Ben Zimmer: Alan Conner put it this way, quote: " to introduce newcomers to the delights of the British cryptic with Listener style puzzles i s a little like persuading people to take a pleasurable, healthy stroll on the weekends by dropping them blindfolded into the Borneo jungle, equipped with a butter knife for hacking through the undergrowth. But you can't blame Sondheim for trying".

Barry Joseph: Welcome to Matching Minds with Sondheim, the podcast. I'm your host, Barry Joseph. As usual, we'll be joined by some amazing people to respond to audio clips from over 60 hours of my original interviews for the book. This time to focus on the topic of Stephen Sondheim and crossword puzzles! Specifically the devious type, known as Cryptics. This is the 22nd episode of the podcast, and it is not a coincidence that it is towards the latter end of the run.

I think I've been avoiding this topic. Why? I don't know. There's just something about it that terrifies me. I had a lot of fun writing about it in my book, but I could not have done it without my hand being held by many of the voices we're gonna be hearing today.

Maybe it just makes me feel stupid. Maybe I feel like it's a language I just can't understand. But I do find them to be brilliant, and there's nothing more I love than watching other people solve them. So today I brought in some remarkable guests to help us better understand this relationship between Stephen Sondheim and cryptic crosswords. Welcome everybody. The first of our four guests is Natan Last.

Natan Last is a crossword constructor and has published crosswords for the New Yorker, the New York Times, and other outlets. He is new to Sondheim and tells me he is kicking himself for not starting sooner. His new book just out is: Across The Universe: The Past, Present, and Future of the Crossword Puzzle. Hi, Natan.

Natan Last: Hey, Barry. Ready to get initiated.

Barry Joseph: Where are you calling in from today?

Natan Last: I am in Brooklyn, New York.

Barry Joseph: What has it been like dipping your toes into this world of Stephen Sondheim?

Natan Last: It's been revelatory. I mean, he's incredible. He's got that puzzle mind and yeah. I'm becoming an obsessive. It's not over yet.

Barry Joseph: It is never over Natan.. Welcome to the cult. Our next guest is Katie Grogg, a singer, actor, and a crossword content creator. As a musical theater performer and puzzler, Katie has always connected deeply with all of Sondheim's work. She's a lifelong puzzler and spends her time teaching people on the internet how to solve crosswords and cryptics, her favorite. Welcome, Katie.

Katie Grogg: Hi. Thank you for having me.

Barry Joseph: Katie, where do you teach people about Cryptics and why are they your favorite?

Katie Grogg: I just started teaching TikTok about cryptics. I started with regular crosswords and we have graduated, so we now do cryptics on TikTok. Cryp-talk, if you will.

Barry Joseph: Love it.

Galen Fott: Hmm.

Katie Grogg: And they're doing great. I'm having the best time. It's very, very fun.

Barry Joseph: I love that you started not by saying I teach people on TikTok, but I teach TikTok.

Katie Grogg: That's right, that's right. The whole app.

Barry Joseph: And where are you calling it from today?

Katie Grogg: I am in New York City.

Barry Joseph: Wonderful. Next up is Ben Zimmer, a linguist, lexicographer, language commentator, and all around word-nut. And not just because he challenged me to read that out loud. Ben is a crossword instructor whose puzzles appear in Slate, Puzmo, the New York Times and many other venues, and he has written about Sondheim's impact in popularizing cryptic crosswords. Welcome, Ben. Where are you calling in from today?

Ben Zimmer: Hi, Barry. Calling in from Jersey City, and really excited to join you. I've been looking forward to this conversation for a while.

Barry Joseph: Wonderful. I didn't know you were from Jersey City. Just like my dad, who grew up there in the 1930s.

Ben Zimmer: There you go. It's a great place to be from. I moved here 20 years ago, but I feel like I'm a newcomer.

Barry Joseph: Last, but not least, I'd love to welcome Galen Fott, an animator, director and actor based in Nashville, Tennessee. Galen is a lifelong Sondheim fan and has acted in two Sondheim musicals. Galen researched Sondheim's cryptic crosswords from New York Magazine and created a complete roster of the puzzles online. Thank you, Galen. Welcome.

Galen Fott: You're welcome and thank you. I'm happy to be here.

Barry Joseph: Are you here in Nashville right now?

Galen Fott: I am, in fact in Nashville. Yes, indeed.

Barry Joseph: So most of us you hear are from the New York metropolitan area. Is there anything you'd want us to know about what crosswords, cryptics and Sondheim are like in the Tennessee area, where you live?

Galen Fott: Wow. I don't think we focus on the crosswords that much down here. Actually. I can't think of anything that would really sort of specifically tie in, Nashville-wise or Tennessee-wise. I spent five years living in New York, so maybe I picked up on it from there somewhat.

Barry Joseph: So if I'm in Tennessee and I have a question about Sondheim, you're the person I'm gonna call.

Galen Fott: I'm certainly one of them, maybe the top five. I don't know.

Barry Joseph: Fair enough. We'll take you! Alright. I have to say I'm feeling a little bit less terrified now, but I'm still virtually holding all your hands and I appreciate it. So, today we'll be digging into the past... but this topic is as topical as ever. Did any of you do yesterday's New York Times crossword puzzle?

Natan Last: Oh yeah.

Katie Grogg: So good.

Galen Fott: Sort of.

Barry Joseph: So Katie, you said "so good." What made it good and why are we talking about it now?

Katie Grogg: I can give spoilers right?

Barry Joseph: Please! Spoil away.

Katie Grogg: Beautiful. Sunday in the park is my favorite Sondheim work. And I was so excited to see that as one of the clues and then to see Sondheim as one of the answers. But the graphic at the end with the "look I made a hat" could make me cry. It's the greatest song in all of Sondheim's work.

Barry Joseph: so for those who don't do New York Times crossword puzzles, when you say the graphic at the end, what do you mean?

Katie Grogg: Yeah. There's not always a graphic is there, but there were some circles that had specific letters in them, and then at the very end, once you solved it, they connected all of the circles that said, "look, I made a hat". That's what the letters made. And it made a hat.

Barry Joseph: And that, of course, is a line from a song in Sunday in the Park with George. So what was it like for all of you new to Sondheim, old to Sondheim crossword lovers, to see Stephen Sondheim being honored in that way within the pages of the New York Times in the crossword section?

Ben Zimmer: Well, I thought that it was perfect timing. It was obviously kismet since we were planning on, recording this today

Barry Joseph: Thank you Will Shortz!

Ben Zimmer: That's right. Perfect timing.

Natan Last: Yeah, and it's actually, it turns out not even the first Sondheim tribute puzzle to run in the New York Times. So there was a link to a couple others. And one of my favorites is a 2005 puzzle clues like, uh, 17. Across is 57 across song about a request in a gene lab across is Stephen Sondheim.

And the answer is "send in the clones". And then 37 across is, you know, a Sondheim song about a request in the maritime supply store. And the answer is "a buoy like that". Um, and it's just those two puns in and out and I really thought that was cute, that Sondheim, of course, continues to be an inspiration for crossword constructors over time.

Barry Joseph: Love it. And I love not only seeing that Stephen Sondheim is an inspiration for people making crosswords. But they're honoring him in a medium that he loved so much, which of course is the topic of today's episode. What was Stephen Sondheim's relationship with crossword puzzles? First, before we get into it, we need to define some terms. The term that's gonna come up often in today's episode is Cryptic Crosswords... the specific type of crossword that Stephen Sondheim loved to do and was a master at creating. So to start, we're gonna go into my archive, and we're gonna hear a definition from Richard Maltby Jr. .

What is a cryptic?

Richard Maltby Jr.: It is a crossword puzzle in which as opposed to a standard crossword puzzle where you were just given a definition. You are given a clue, and the clue is something that looks like a sentence or a fragment of a sentence or a phrase, but is in fact a veiled way of telling you the answer. Any clue has a definition and then a secondary description of the word, how to spell it, an anagram of it, an anagram of the letters in it, a combination of that, a homophone for it or any other way that you might want to spell it. All in language intended to just confuse you.

Galen Fott: Well, yeah, that's a great description. Absolutely... of what Cryptics are. From someone who has made so many of them. Maltby was one of, I think maybe the very first person to fill in when Sondheim started in the New York Magazine puzzles. Perhaps, I'm just guessing he had trouble keeping up with the schedule 'cause he was busy writing Company and Follies at the same time! And so Maltby is one of the people that came in and contributed puzzles, when Sondheim, uh, didn't have one that week.

Barry Joseph: And in fact, this month, January marks the 50th year of Richard Maltby, constructing on a monthly basis crosswords for Harper Magazine... having learned how to do it from Stephen Sondheim.

Ben Zimmer: Richard is clearly a master of the form and, one of the great American cryptic crossword constructors. But it should be noted, of course, this is originally a British form that was adopted by various Americans, including Sondheim. But was really developed and cultivated in the British crossword scene. Even though crosswords are originally an American invention, they've crossed the Atlantic back and forth a few times in terms of their influences and development.

Barry Joseph: So let's talk about why we're talking about Cryptics. What do Cryptics have to do with Stephen Sondheim first? To do that, we'll listen to another set of clips. We're gonna start by hearing from Stephen Sondheim himself. This comes from an interview he did for Games Magazine in 2020, and we are listening to a recording of the phone call that was used for transcription purposes. Which I was given permission to share today. So it's not perfect, but it's Stephen Sondheim's voice. So we'll start with that and then we'll hear a little bit from my conversation with Will Shortz on the topic and bring back again to round it out, Richard Maltby Jr.

Stephen Sondheim: So I take virtually full credit for

for introducing cryptic space.

Barry Joseph: What are the key characteristics that you see of a mind that adores crossword puzzles?

Will Shortz: Wow. Well, obviously you love language. You like to be challenged, you like to be tested. You need to be a good crossword solver, you need to know a little about everything.

I think the biggest characteristic of crossword people is flexibility of mind to be able to look at a clue and see the many different ways it could be interpreted and figuring out which one is correct.

Richard Maltby Jr.: So these puzzles are, again, a technical exercise in language. So it's not surprising. Sheldon Harnick used to do these puzzles. Steve Schwartz went into it for a while. Lyricists respond to the technical fun, and the pitfalls of the English language. I mean, how many sentences are there that seem to be about this? But they could also be exactly the opposite.

Barry Joseph: And if the audio wasn't clear, what Sondheim said in the beginning was "I take virtually full credit for bringing cryptic puzzles over to the United States."

Ben Zimmer: He can take most of the credit. There were precursors who were doing cryptic crosswords, particularly in the nation. And occasionally in the New York Times before Sondheim was publishing them in New York magazine in the late 1960s, but he can take most of the credit.

Barry Joseph: So Ben, in the New York Times, I believe what you're referring to is the puns and anagrams. Is that the, am I getting the title there correct?

Ben Zimmer: That's right. There were, uh, from the beginning of the New York Times publishing crosswords originally just in the Sunday, New York Times Magazine, starting in 1942. They included what we might call sort of light, not quite full fledged cryptics as they developed in the UK.. And those were called puns and nanograms puzzles. And in fact, Stephen Sondheim, enjoyed those as a child. He's talked about this in interviews where he recalled when he was introduced to puns and anagram puzzles, by his mentor Oscar Hammerstein, because when he was a teenager, he was spending a lot of time at the Hammerstein House in Pennsylvania. And, that's where he was first exposed to, not quite cryptics, but again, these puns and anagrams, which use a lot of the same techniques as cryptic crosswords in terms of their word play. So in fact, Sondheim recalls when he was about 14 years old, he decided he was gonna make his own and submitted to the New York Times. And he says, they sent it back saying: "We're very impressed. It's very perspicacious, which was a word I had to look up". So that was, his first attempt at crossword Construction in the style of puns and anagrams. And, it would take till he was an adult before he was a really full fledged crossword constructor.

Barry Joseph: And that training that he received from the puns and anagrams column continued when he went to college, when his friend Burt Shevelov introduced him to the weekly cryptics constructed by Frank Lewis for the Nation. And this was the first time Sondheim experienced crosswords that relied exclusively on cryptic clues.

He said about them, they have gimmicks. Some are in a code, and you can't figure out the code till you solve the puzzle. And you can't solve the puzzle till you figure out the code. And by the time we're now into his work on West Side Story, he's now in his twenties. It's the 1950s, he's discovered the British cryptic puzzles.

Can anyone here say a few words about what the British cryptic puzzles were about? Anything about that community or where they came from. That history leading, leading up to the 1950s when he heim began picking them up every Thursday when they arrived overseas.

Natan Last: One of the interesting things is that for a while, British style puzzles were actually American style puzzles. So these looked just like the puzzles you'd see today in the New York Times, more or less, but more like the puzzles you'd see in the New York world when the First American style crossword is published in 1913 by a Liverpudlian and Arthur Wynn. So the Atlantic Crossing is constant in the history of the puzzle and. Of course at the time the Brits were aghast at the American Obsession with Crosswords. And there's a famous article in the London Times in 1924, imperiously titled An Enslaved America. And you know, the author is tallying up the number of working hours that American, gadabouts and layabouts are devoting to this idle, trifling. But in the late twenties, there are early intimations of cryptic crosswords. And then I'll pass to band to talk about the shift to cryptics.

Ben Zimmer: Yeah. So, there was one cryptic crossword constructor or setter, as they say in the UK who really kind of initiated this revolution. And, his name was Edward Powys Mathers. He went by the pen name Torquemada. , After the figure from the Spanish Inquisition since he was kind of torturing you with his puzzles. So for a while, he developed this, uh, style over late twenties into the 1930s. For a while, those puzzles were just called Torquemada style. But that became the sort of recognized style that was picked up by many UK newspapers and other publications in the 1930s, especially. And then, Americans start noticing, you know, , those British people, they're doing something different with these crossroads. And, eventually that ends up filtering back, uh, to the US. And, by the time that Sondheim is really getting into it in the 1950s, there are these very elaborate, what we would call variety cryptics that involve a theme and some sort of gimmick that can get very complex. And the hardest ones to solve came from The Listener, which of course is what Sondheim gravitated to. 'Cause they were the most diabolical.

Barry Joseph: So The Listener, I believe, came out on Sunday. So that meant for a New Yorker like Stephen Sondheim, who wanted the best and the hardest Cryptics, he had to wait till Thursday. And Thursday morning when Stephen Sondheim would pick up his copy. That meant all work would stop on West Side Story. And in our next set of clips, we're gonna hear a little bit about that from Richard Maltby Jr. And then we'll hear a little bit more from Stephen Sondheim from that Games magazine interview with Andrew Parr, and again, Richard Maltby will return to wrap that up.

I mean, he and Bernstein would sit in the theater at West Side Story doing British cryptic puzzles. I mean, it was a thing.

Stephen Sondheim: After I'd done for a while, then I became aware of The Listener, which was more difficult, although the Ximenes puzzles was not that easy. And um, so that's when, when we were writing West Side Story, I introduced Lenny to the cryptic puzzle. And when what, like an interesting one would come, I bring it down and instead of working spend a day doing the puzzle, I can remember some of those puzzles vividly because they were so intricate and imaginative. And, um, so as I say, I borrowed some of the ideas, but I always gave credit.

Richard Maltby Jr.: In fact, one time I was at some sort of gala and for some reason I was seated next to Leonard Bernstein.

I mean, I was sort of.... verklempt. When I was sitting next to Leonard Bernstein and all he wanted to talk to me about was cryptic puzzles. He knew I did them and you know, and that's what he wanted to know about.

Ben Zimmer: You might have just heard the name Ximenes in there. So that's another pen name. This is something that , the British cryptic crossword setters started doing with Torquemada. So Ximenes - actually I think he pronounced his name as Ximenes. He was, setting cryptic crosswords, for The Observer.. So in real life, he went by the name Derek Somerset McNutt. And he's famous I think for kind of really standardizing the rules, you know, Torquemada started this whole process. And then, Ximenes or Ximenes was the first to really kind of, give a set of guidelines that everyone followed to sort of make it fair and you knew what to expect in cryptic crosswords.

Galen Fott: I looked up, - I was curious because in every Sondheim puzzle, he always says, you know, gives a little mention of credit, like he said in the clip to the originator of a puzzle in The Listener. And I was curious and I found at Vanderbilt University, an archive of old Listeners and I was like, I'm gonna find one puzzle that he was clearly, inspired by. And I was able to find one or two. I came away with the conclusion that he's really pretty generous in acknowledging, the originators of The Listener puzzles, because Sondheim's puzzles are entirely his own work. It really was just sort of a, a germ of inspiration, I believe that he founded in those.

It's not like he just Americanized a few clues and sent it out there you know. They're his work.

Barry Joseph: Galen, I think you're right. And for those who are new to cryptics, it's important to remember that on one hand you had individual clues that you were solving and then writing those words into the grid. But that cryptics, as you mentioned earlier, always had a theme, a meta puzzle. And they were different every time. The one we started today's episode with was the fact that there was gonna be a hat that was gonna be drawn out by the letters at the end. And that's the fun extra piece, except the meta puzzles for these cryptics were so insanely complicated. One, for example, is you fill in all the words in the crossword, and that's the beginning. Some of the lines are thick, you cut them out, and now you have jigsaw pieces. You put the jigsaw pieces together, and now you finish the jigsaw. That's end of the second puzzle, and that then puts words together, and those words make out an entire logic puzzle. You have to solve the third one. And so when Stephen Sondheim was acknowledging the people who inspired him in England, what he was often doing was acknowledging the people's meta puzzles that he was copying. So I think one of the puzzles you'll be familiar with, Galen, is called Chop Logic and it's called Chop logic. 'cause you're cutting it up to do the jigsaws. And so when he's thanking someone, he's thanking them for the menopausal and he's reusing that. But like you said, Galen, the rest is all Sondheim.

Katie Grogg: Barry, I'll just say in regards to what you just said about the meta puzzle, I just, last year started making my way through Sondheim's Archive of New York magazine puzzles, which I actually found thanks to Galen.

Galen Fott: Hmm.

Katie Grogg: So thank you I still feel new to Cryptics, even though I've been doing them now for about four years. I feel like I'm just starting to understand them. So diving into Sondheim's puzzles, I mean, there's nothing more gratifying than being able to solve one of his. Can't believe it. But going and just looking at it, the instructions take up like half the page. He can't help himself. It's like seven layers deep. So, it's no wonder that this could be like a scary territory for people who have never seen Cryptics before. I would say if you started with Sondheim, you'd probably just end right there.

Barry Joseph: I appreciate that, Katie. Anyway. So the people we're talking about now, these British cryptic constructors. Ximenes, of course. Derek McNutt, who was kind of the leader. The Will Shortz of his time, so to speak. But then all these other people, the individual constructors.. Stephen Sondheim spent a decade, a decade and a half, maybe two in New New York, solving them as they came over every week. But then in 1968, he got to meet them in person. I'm gonna read now a short excerpt from my book that talks about Ximenes' 1000th, cryptic puzzle. Now, Derek McNutt, that's much easier to say, made a tradition of when he hit milestones, having a party. The 100th puzzle published. 250th. 500th. And it was 1968 when he hit his 1000th puzzle.

And there was a big dinner being held for Derek. At the Cafe Royale in London. And it just so happened that, A Funny Thing That Happened on the Way to the Forum, that Stephen Sondheim created with Burt Shevelov was going to be in London, and Shevelov loved doing puzzles with Stephen Sondheim as much as Sondheim loved doing them. And Shevelov said, why don't you come over for it? Come be here for the show. Come here for our show, and then we'll we'll go to the party. And so something happened. Shevelov was supposed to have gotten the tickets. He said he contacted them, but when they showed up at the door, they said, I'm sorry, we don't have any tickets for you, and this is invitation only. Sondheim then says, you know, I've come all the way from America. Maybe you can find a way. And they did. Everyone had a number on their seat. So maybe Katie, you would be number 37 and, and, uh, Natan, maybe you're gonna be, uh, 94. Well, Stephen Sondheim was 00, because they had to create it from scratch. And Sondheim described the room: it was a very large dining hall. The tables were long, like a day table, like a bird's eye view. If you look down, it was like four tables with one facing all of them. There was a column in the paper at the time who described the event as 360 uniquely gifted people who can actually do Ximenes' puzzles all there to celebrate the occasion by having Mr. McNutt to dinner at the Cafe Royale where they toasted him as "the maestro". That letter M in Maestro was intentional and in joke on the theme with the evening. As the Roman numeral for the number of thousand is the letter M. The character would appear throughout the night.

The menu was turned into Millenu, serving Moracambi prawns, ministroni, mutton, mashed potatoes, marrow, moose, mocha, and mac nuts. And then all the speakers for the evening all began with letter M. And then Sondheim told, Andrew Parr for Games magazine. " Because it was the 1000th puzzle and Ximenes was often referred to as X, everyone Intendance got a puzzle that had to do with Xs and M's and all the Roman numerals." After all the evening speeches, it was time for Ximenes to share a few words of his own. According to Sondheim, he said. Over the years I've had many distinguished solvers like the Field, Marshall Montgomery, and then he named a bunch of celebrities and they concluded with, tonight we have a visitor from America, the man who wrote the music to West Side Story, Stephen Sondheim. It was a round of applause, and as it died away, Stephen Sondheim yelled out to the entire room lyrics, not music. He told Andrew Parr. That was my highlight of the evening. In reflecting on that story, Sondheim said all these people, most of them who made puzzles, I got to know a couple of them. And he did. And as a result of that, he became part of what has come to be known as Apex, a puzzle every Christmas. Now, were any of you familiar with Apex or Eric Chalkley who also used that nom de plume Apex?

Ben Zimmer: I learned about all that from reading your book, Barry.

Barry Joseph: Well, I'm so excited that I have something to contribute to this incredible community of knowledgeable crossword aficionados. When I started researching my book, people would say, oh, you have to look into this club that Sondheim was part of in England, or this group of people who we knew. No one knew exactly what it was. Was it secret? Was it invitation only? And in fact, it was invitation only, and it was really exciting to get to the bottom of who was Eric Choley? What was Apex and why was a carpenter in England, someone who would engage and entertain Stephen Sondheim with cryptic crosswords for decades. So in short, Ximenes not only constructed crosswords in England. He also wrote a book. He wrote a book to teach anyone who wanted to learn how to design their own. He didn't think it was a special ability. He thought anybody could learn it. And Eric Chalkley as I said, just a carpenter, who's looking at these really obscure, obtuse puzzles every week in the paper. And felt confused by them, challenged by them, but also curious. And so he picked up Ximenes' book, which challenged the readers to make their own. And he said, once he got to the end, I now understand how this works and I'll see what I could do. And he did. He created one, sent it to Mr. McNutt, who promptly wrote it back and tore the shreds. But that was done with love. It was done with love. as a teacher to a student. And that is how Eric appreciated the comments. And he worked on 'em some more and sent them back and got less comments. And he kept doing it until he got a, essentially a version of a thumbs up. And that started Eric making encrypted crosswords and then submitting them to the paper where they then got published.

One of the things that Ximenes did that was special was he left one of the clues to be constructed by the readers. That is, it was just a straightforward clue. So it was obvious. But your job in reading it that day was to write him back and say, here is a great cryptic clue you could have used. Ximenes would then put together the best ones and send them back out to everyone who submitted them. So imagine. This was his own way of creating a social network through mail where anybody who dared to step up and try and suggest what their own construction might be, could both get feedback and learn from it and see the best of the group creating a kind of a community. And this would happen every week. Eric saw this and thought, one, this is incredible. And two, how unfair that Mr. McNutt doesn't get to experience this. I want him to have his own experience. And so Eric decided to bring together people who were at that 1000th party from all over the world and create through mail an opportunity for Derek McNutt to get to also be one of the people who are contributing. And one of the people that Eric included was Stephen Sondheim. And when it came time to naming it, he decided to pun his own name. So Ben, you explained that Torquemata was the nom de plume of one of the original creators of cryptic crosswords, and then he inspired Derek McNutt to take on the name of Ximenes, who is in the real world, the mentee of Torquemata. And Eric wanted to continue that line. And so he calls himself Apex. That is A-P-E-X because he ate Ximeness. Apex. So his nom plume was Apex. And when it came time to name his invitation only Mail community, which he sent out on Christmas every year, he called it Apex. But all capital. A puzzle. Every X-mas. Every Christmas.

And that's the origin of Apex. And so every year, Stephen Sondheim and then others who would join Leonard Bernstein, Will Shortz, would get a cryptic crossword with one of the clues. Being just straightforward, where everyone would again, try and come up with the best. Everyone would contribute some money, and, uh, Eric Chalkley would then donate it to a good cause. Later in his life when Eric was about to pass away, many in the community wanted to honor him. His community nominated Eric to be recognized for his work in crosswords. And three people submitted letters that were to go to the Prime Minister's office to advocate for Eric and one of those people was..

Ben Zimmer: Sondheim

Barry Joseph: That's right. And unfortunately we do not have that letter today. But the person who did submit it said it was a very nice letter and it advocated for the crucial role that Eric played as Apex promoting cryptic crosswords throughout England and from there around the world.

Katie Grogg: The thing that I have to offer about that, and that kind of stands out to me is where he started versus where he ended. Eric... because my whole shtick online is that anyone can solve crosswords. That's the whole point of doing it, of starting my channel and all that stuff. And even something as insane as cryptics and how they feel so convoluted and so impossible with practice kind of what we heard in one of the clips we listened to, like your brain starts to change. You start to see things differently. And in fact, like in my experience, I see the world differently. I've got my head on a swivel at all times for wordplay. I feel like crosswords and wordplay are the lens through which I see the world, and once you start to your brain kind of shift in that way, it becomes totally possible the thing that you thought you simply didn't have the smarts for. So I just think that's really interesting how he was able to start from getting bad feedback to creating an empire.

Barry Joseph: That's beautiful. Katie. I think that speaks to one of my favorite things about the values I see in Stephen Sondheim's designs, which is that they're very democratic. They're designed for anyone to be able to participate in the process. And that's also something that you're seeing in the British cryptic community, and I saw that as well, which is one of the reasons why I loved writing about it.

It's just such a wonderful community.

So here we are. In 1968, Stephen Sondheim connects with the British cryptic community For the first time in person, maybe it's a Saturday. It was a weekend. And then that Monday, his first cryptic crossword was published when the first issue of New York Magazine came out, and he was the founding puzzle editor.

Ben Zimmer: So right when Sondheim is, uh, really getting immersed in the world of cryptic crosswords Clay Felker, who is the co-founder of New York Magazine, asks him to contribute a crossword to that magazine's very first issue in April, 1968, and that would become his regular gig for about a year and a half. Although his frequency of crosswords,, declined. Over that period, he was getting a little too busy working on Company and, he couldn't devote so much attention to making these crosswords. And in that very first issue in April, 1968, he gives this introduction to how Cryptics work. In the same time he ends up kind of slagging American cryptic crosswords, for being sort of lesser puzzles, which, rankled American, , puzzle people. They didn't really like that these American crosswords, that Sondheim was treating as, not nearly as clever as these amazing British creations that he was trying to introduce to an American audience.

Natan Last: Yeah. He says something like, there are crossword puzzles and then there are crossword puzzles. Right, right. And he doesn't like the American style puzzles, which tend to have wider open expanses of crossing words. The British style, you know, these look like lattices. Or sort of waffles. There's fewer crosses. The American style, because there's an increased density in interlock. You do sometimes have obscurities and Sondheim hates these. He rages against... " Brazillian potter's wheel" or obscure nuts from places he's never been, right? So, the idea is that the British style, by giving you clues and riddles and helping you build the word up through these instructions, is just a test of cleverness and not a test of your mastery of esoterica.

Barry Joseph: Sondheim's opening essay did draw a line saying the American style is on this side, and I'm clearly here on the British side. But that essay did more than that. It was also designed to introduce Americans to Cryptics and how he was gonna adapt them for an American audience. Does anyone feel like they can reflect on what it was he did in that essay that allowed Cryptics to transition to America in a way that it could finally stick?

Galen Fott: It's an incredibly thorough, and delightful as well, explanation of how cryptics work in the various, formats that the clues can be in. If I may, I just wanted to read my favorite line where he talks about solving cryptics. He says it's a matter of mental exercise, not academic clerk work, and all it takes is inexhaustible, patience, limitless time, and a warped mind.

Barry Joseph: I love his all that it takes. That's the best.

Ben Zimmer: Well, the essay itself is a wonderful piece of writing. It did annoy people though. There was a letter to the editor, in the following issue from David Schulman. Who was someone I actually knew when I was a kid, when I was a young puzzler, , back, in the 1980s when I joined the National Puzzlers League. David Schulman, by that time, was in his seventies. But I got to actually know him, and he responded to that essay from Sondheim saying. What are you talking about? American puzzles are the real crosswords. These British crosswords aren't the real ones. And he kind of went overboard railing against cryptic crosswords, talking about, you know, Americans have the real, real deal. But you know, he did sort of point out some hypocrisy there where Sondheim's saying, oh, all of these obscurities that you have to know to solve an American crossword. There are still plenty of obscurities... If you were actually trying to solve a crossword from the listener or one of the other leading British papers, there would still be things you'd have to run to the dictionary. They use, often Chambers dictionary as their reference of choice, stuff that is super obscure. So, fortunately Sondheim, when he, introduced his crosswords... he toned that down. So yeah, he really didn't want there to be anything that was super obscure in his crosswords. But the ones he was modeling, , his crosswords on, yeah, they could get just as obscure as American ones.

David Schulman writes this letter to the editor, taking exception to Stephen Sondheim's introductory essay, which was called How to Do a Real Crossword Puzzle, and said, no, no, the real one is, the American Style. And he ends it by saying, I have over 25 years experience, and he signs off. David Schulman, associate editor of Complete Crossword, Tiptop Crossword and Original Crossword Magazines.

Barry Joseph: I love that there's three different ones that he's editor of. That guy's qualified

Ben Zimmer: For sure.

Barry Joseph: Schulman was not the only one in New York Magazine to critique Sondheim's Cryptics and how challenging they were. And we get to see that a year later when the issue to recognize and celebrate printed parodies of everything it had done.

So I'd like to invite you all to read for our listeners what it said and describe it where it's only visual. And just to go around. Okay, great.

Katie Grogg: It's titled Do I Hear A Waltz by Stephen Sondheim with some redactions in his name. And then it's followed by what looks like a musical clef, mixed with a crossword grid. It says the diagram represents a musical staff in the G clef. Consonants occurring in the answers should be entered according to their appropriate musical position on the staff as shown by this chart.

Barry Joseph: I'm not a musician. Katie, when I see all these letters in the chart, does that mean something to you as a musician that you understand that I don't.

Katie Grogg: I mean, yeah, they usually do. These are a little, , off the normal scale, I would say.

Barry Joseph: Okay.

Katie Grogg: Um, yeah, we've got our normal E-flat fg. I love those notes. And then there's SKY, I don't know those notes, but it seems that this is, this is our, this is our code.

Barry Joseph: Who wants to pick it up?

Galen Fott: The solution consists of 21 4 letter words and 4 21 letter words. Vowels Vowels when used in answers are subject to transposition according to the key signatures following each definition. Remember, diagram is in E flat. When the diagram is completed, the filled in o's if played on the piano will be the minute waltz.

Natan Last: Answers contain six Serbo-Croatian words, a Nicaraguan idiom, 11 words made up by the author. Four outrageous puns and a farfetched definition of tinderbox. Three of the definitions are in Norwegian, and two must be held up to a mirror.

Ben Zimmer: One letter in each answer does not fit into the diagram. These unchecked letters may be rearranged to spell I hate you Stephen, S-O-N-D-H-E. Ignore punctuation, which is designed to confuse.

Barry Joseph: And as many of you know, that last line, "ignore punctuation", is how Stephen Sondheim ended all of his instructions for all of his cryptics in New York Magazine.

Ben Zimmer: It's a great parody, just of the many layers that would go into these Listener style, variety, cryptic crosswords where, you know, you solve it and then there's another step, and then another step and another step of often involving kind of different genres of puzzle making, kind of being, amalgamated into one puzzle. And so it's a lovely parody from someone who had clearly tried to wrap their brains around these, diabolical puzzles that Sondheim was presenting in New York Magazine.

Katie Grogg: Yeah, I would say it really does feel this way. Like this is what it feels like to be attempting a Sondheim cryptic for the first time.

Ben Zimmer: I wanted to share a quote from Alan Connor. He is a cryptic crossword setter for the Guardian and the Observer. And he wrote a book called The Crossword Century, when the Crossword was celebrating its centennial. And he talked about these, Sondheim puzzles, that were modeled on the Listener.. Alan Conner put it this way, quote, to introduce newcomers to the delights of the British cryptic with Listener style puzzles i s a little like persuading people to take a pleasurable, healthy stroll on the weekends by dropping them blindfolded into the Borneo jungle, equipped with a butter knife for hacking through the undergrowth. But you can't blame Sondheim for trying.

Galen Fott: That is perfect.

Barry Joseph: Lovely. So at this point, we're now a year into Stephen Sondheim making cryptic crosswords for New York Magazine. Starting initially with one a week, which is just remarkable. By the end of his first year, he took a break every once in a while, and his friend and fellow lyricist, Richard Maltby Jr, loved doing them, had learned about them from his friend Stephen Sondheim, and couldn't bear the idea of them not being in print for one week. So Richard took his hand at creating them and had a few submitted, and by the time Stephen Sondheim in his second year decided he needed to stop doing it and move on to work on his new show, Company, Richard Maltby Jr said, could I step in? And so what we're gonna listen to now is a clip of what it was like for Richard Maltby to be mentored by Stephen Sondheim, not for writing music or lyrics, but for constructing cryptic crosswords.

Did you and Steven ever solve them together?

Richard Maltby Jr.: The only thing that we did was when I started doing them, I would always send the puzzle to him and then we would get on the phone and have nitpicking... where is it fair to have as a dividing line between the two parts? The word "for". FOR, you know. This for that, or should it be "from" or into or, you know, some we would, we can go go on for hours, well minutes about whether it was a fair use of the meaning of the word. But you know, that's what lyric writing is. You're so responsive to the actual meaning of the word to make sure it doesn't mean something else. You know.

Natan Last: Yeah. So I mean, one of the things you hear in that clip is this idea of the lyricist and the crossword setter being technicians in a similar way. And Sondheim was actually one of the pioneers and formalisers of the way cryptic Crosswords should connect their cryptic section and their definition section. So a clue, like.. "She screams, em dash, don't allow her if you hear it"... is a clue for the word Banshee. " She screams" is the direct part of the clue... "don't allow", is a synonym for the word "ban". " Her" is "she".. SHE. And if you hear it, you're hearing a homophone for the word shee, right? SHEE. And so you get Banshee when you put it together and that em dash links the cryptic part of the clue to the right of it and the direct part of the clue to the left of it. And so from, and for, and all the ways of connecting the cryptic part and the definitional part would be the kind of thing that a setter would really, labor over in the same way that, you know, Sondheim hated near rhymes, right? And treated the search for the perfect rhyme as a logic problem. You can imagine treating the search for the perfect, linking word in a cryptic clue that still gives the clue some kind of surface sense. That's another thing we haven't talked about. Cryptic clues are beautiful when like "she screams, don't allow her, if you hear it". Sounds like a sentence, a poetic one from some kind of fairytale... but "if you hear it" indicating the homophone and "she screams" indicating the banshee sort of have less to do with each other, then the sentences syntax might have you think.

Barry Joseph: So here we have Sondheim in his late thirties mentoring a friend and colleague on how to create and construct cryptic crosswords. And I wonder if those who are more familiar with Sondheim hear echoes here of the elder Sondheim who spent much of his time mentoring in musical theater, performers and writers.

Katie Grogg: My love for Sondheim runs very deep because I did not start out loving him as a puzzle person, as most people don't. I know him as the prolific musical theater composer, and he's composed all of my favorite shows. And it took me a while to realize that the reason that I love them so much is because they behave like puzzles. And the little motifs that you hear in one song that show up in another song tells its own wordless story. And you could go 7, 8, 12 layers deep in all of his compositions in the same way that you can go 7, 8, 12 layers deep in his cryptic crosswords. And so him living at that intersection is the thing that, whether I knew it or not, was connecting with me the whole time. And I think at the end of that clip, when they start to mention the, like lyricism and how that is its own puzzle and you're trying to find the exact right word, you're trying to find the true rhyme. There's a real alignment there. I think to your point, Barry, like , he can't help himself and so the mentorship of him and Richard Maltby is... I think back to videos I've seen of him, like in masterclasses and things like that. And it's all so specific. Everything is always so specific. So long answer to your question, yes.

Barry Joseph: Thank you, Katie. We're about to leave his time as puzzle editor. Is there anything else everyone wants to comment about this time in Sondheim's life or the crosswords that came out of it?

Galen Fott: There are a couple of interesting things where echoes from his life and even his future work would appear in the puzzles. Like the one where one of the clues was Seurat.

Barry Joseph: Please, please say more.

Galen Fott: Absolutely. Right. . So, it's the puzzle for October 21st, 1968. The puzzle is called intermediaries. And one of Sondheim's clues is as follows. French painters works could make us stare. French painter's works, could make us stare. So, leaving a little, a little time for people to think on that. And I'll go ahead and it has important to say the answer has seven letters. So part of the clue obvious is French painters in the possessive with the apostrophe. And then us stare is the anagram for, as it turns out, Seurats, S-E-U-R-A-T-S.

It makes you wonder how much was Seurat on Sondheim's radar before he and James Lapine wrote Sunday in the Park, which was inspired by Lapine bringing a postcard of the painting to one of their brainstorming sessions. And they decided to write a musical about that. But, you know, Seurat was at least a little bit on Sondheim's radar even way before then. Sunday In the Park was 1984, and that puzzle is 1968.

Barry Joseph: Galen, that is a remarkable detail. Talking about life rhyming. That's a perfect example. So Stephen Sondheim leaves New York Magazine. He leaves the puzzles in the hands of his friend, Richard Maltby. He goes on to do Company and he stays in the world of musical theater. And yet the puzzle still followed him because in the early eighties, New York Magazine published a collection, two collections, actually, one tends to overshadow the others. One is a collection of Stephen Sondheim's cryptic crossword puzzles, and the other is Richard Maltby jr's cryptic crossword puzzles. But it is Sondheim's book that we hear about the most. It is Sondheim's book that will cost you thousands of dollars if you wanna buy an original copy on eBay. And it is actually, I think, the version that most people come across because you tend not to find the ephemera of a magazine from 1968. As much as you might be able to find a book, even though that book itself was paper and, was meant to be written on and and thrown away.

Galen Fott: For the listeners I'm holding up. My copy of Stephen crossword puzzles from New York Magazine.

Barry Joseph: This became one place where people could go to access the majority of Stephen Sondheim's original cryptic crosswords. I think he created originally 42, so I believe the book has 41. Can anyone talk about the impact the book had on the crossword community?

Ben Zimmer: Well, I heard about this book without ever seeing it for many years. Uh, it was just this legendary book that few people had. Um, and so it, it circulated as far as I know, in the crossword community originally, just as this kind of Samizdat underground publication. That was photocopied. I remember that John Delfin, who's a great, crossword solver.... many time champion of the American Crossword puzzle tournament. And also a piano accompanist, just someone else who combines love of music and love of crosswords. He was sharing, photocopies originally , and that was sort of working its way through. And then eventually he was, scanning that for people to share. And so it was all circulating and you had to know who to ask basically in order to even get a photocopy of it.

Barry Joseph: And Katie, you've mentioned that you've been working your way through Sondheim's crosswords. Where are they coming from? Are they from a copy of the book? Are you reading in the original New York magazine.

Katie Grogg: Well, it's interesting, Ben, what you just said, because they came to me kind of in a roundabout way. They came through my musical theater experience. So bit of a backstory, but I was in an audition and on my resume I have my, you know, internet handle on there. And so the casting director who was there was like, oh, you do crosswords? I was like, yes. And I was like, can't wait to talk to you about this. So we had a long conversation, me, him, and the accompanist who was in the room, and they brought up Dan Feyer, who is also a renowned. American crossword puzzle tournament champion many times so they mentioned his name. And he's also a music director and a pianist, so also lives at the same intersection as, you know, Sondheim in that, you know, music and puzzles world. So he had a long conversation about that and it moved after that to email and we emailed back and forth. And then he is actually the one, that casting director is the one that sent me Sondheim's puzzles for the first time. So he emailed me the photocopy PDFs from the book. It wasn't, I don't believe that he has the book. I believe he probably found it through Galen. And Galen and I had come upon your blog as well...

Galen Fott: okay.

Katie Grogg: After he sent me that and I was like, oh, it's so, it is somewhere you can find it. And I was like, oh my gosh, I can't believe I'm looking at these. Like I, I never would've imagined that I would like attempt anything like this. so I sat down one night and I opened up the very first one and I was like, let's see how this goes. And it took me a few hours, but I finished it. And it is one of the most gratifying feelings I've had in solving. So yeah. Interesting that it came through musical theater for me.

Barry Joseph: Galen, what blog is this?

Galen Fott: Oh, this is blog fought@blogspot.com. My name being Galen Fott. I couldn't think of anything better to call it. And yeah, it's just various things that come into my mind and little discoveries. I feel like I've made that. I haven't found anyone else on the internet who said this, so I'm gonna just put it out there. It's easily findable. Blog fott@blogspot.com. That's where I first posted, my list of the Sondheim crossword puzzles. I discovered, just through Googling around I found one or two of them, and then one of them was on Google Books. So I said, well, that's interesting. Don't tell me that Google Books has all of New York Magazine archive.

Well, they don't have all of New York Magazine archived. It's a very spotty collection. There was no easy way that I could find any way of even figuring out which issues they had. So I really kind of methodically started making a list and I ended up contacting New York where for I think $10, they will send you a color copy of an article or whatever you're looking for from their printed archives of old New York copies. So yeah, I sort of systematically kept hitting them up for, you know, how about this issue? I got to where I could ask them you would look at it and tell me if Sondheim did the puzzle or not. I would appreciate it. And also if the answer to the puzzles is, is to one of Sondheim's puzzles. So over a period of several months, I eventually was able to compile, the list of all of the puzzles that he made with links on my blog, to the pages on Google Books where you can find the puzzles and work them yourself.

Barry Joseph: And the answers as well.

Galen Fott: The answer is as well, where, where available. 'Cause it, it's frustrating sometimes there's the puzzle, but the issue that had the answer in it isn't archived on Google Books. So I think I managed to find a legal way to share this information as opposed to the fellow who was notified that he needed to take down his website.

Ben Zimmer: Yeah, so there was a, a website on Angel Fire, which was, you know, this bygone web hosting service, where someone had put up PDFs of a photocopy of the book. And I know that was in existence in like '09 to I think 2011. it actually got a little recognition. There was like a New York Times blog post about it, which probably brought it too much attention because, it got shut down shortly thereafter. And then we had to wait until, you know, Galen, what was it, 2014, I guess when you

Galen Fott: I, I think so. Yeah. I think in that same article that was in the Times, they were trying to figure out who actually owns the copyright to them. And I believe Sondheim is quoted as saying he didn't know if it was him or the magazine.

Ben Zimmer: So yeah, in 2011 on the New York Times Blog Arts beat, Patrick Healy, wrote about this, website that was originally sharing, the scans from Sondheim's book of Cryptics. ' And so they checked in with Sondheim. And, he had said actually that he had no problems with the cryptic puzzles, appearing free for all on the internet, saying quote, "it's fine to have more people learning about the games and enjoy them." He said he was not sure who held the copyright to the puzzles. Since they were published in that 1980 book. And so, that's where things stood. But then shortly thereafter in 2011, that website they're talking about was taken down.

Barry Joseph: So let's talk now about the impact Stephen Sondheim has had on the world of puzzles in general on cryptic crosswords, through his time at New York Magazine and the reprinting of those puzzles. When I talk publicly, as I go around on my book tour for Matching Minds with Sondheim, I often say the following, " that even if Stephen Sondheim had not written a single song in his entire life, still would've had an obituary in the New York Times when he passed away simply because of the impact he had in the world through his cryptic crosswords."

Do you agree with that? Do you disagree? What are your thoughts?

Ben Zimmer: I would say there was definitely a ripple effect that happened starting with those, cryptic crosswords that Sondheim published, and then Maltby took up the mantle after that. Because that had a big influence on, some young puzzling types who are coming of age in the 1970s. And then. In the 1980s, especially where cryptic crosswords were becoming a more, you know, recognizable puzzle type that you would see in US publications. And we really can trace that back to Sondheim and everyone who tried to sort of wrestle with these puzzles. I'm reminded of the famous quote that Brian Eno said about the Velvet Underground that... they only sold 30,000 copies of their first album. But every one of those people ended up forming a band. So, I don't know how many people were actually, you know, solving those puzzles, but a lot of them did go on to become puzzle makers themselves. Maltby, of course, is the, the great example, but he was being directly mentored by Sondheim. , Another notable example of this were, was, the, the great husband and wife, puzzling duo of Emily Cox and Henry Rathbone. They go by the shared pen name of Hex. They got their start, with cryptic crosswords by doing those Sondheim puzzles. After Sondheim passed away, I wrote a piece for Slate just talking about Sondheim's, puzzling legacy. And so I got in touch with, , Emily Cox and Henry Rathbone to see, you know, what effect Sondheim had on them. And, they said that, it all started because, Henry Rathbone's father had a stash of photocopies of those original Sondheim cryptics. And one day in the summer of 1976, they just decided that they would try solving them, and it just like opened up a whole world for them. Shortly thereafter, I think just in 1977. They end up starting to make cryptic crosswords for the Atlantic. And so they're starting that. Richard Maltby, and his collaborator Ed Galley, are making crosswords in Harper's Magazine. So it's taking off as perhaps a kind of a highbrow, puzzle type that you might see in a magazine like The Atlantic or Harper's, and that all directly flows from Sondheim.

Then starting in the 1980s in particular, we get a whole new generation of puzzle makers who are making puzzles for Games magazine. That's when Will Shortz is there. But we have great, crossword constructors, people like Mike Shank, Henry Hook, Merle Regal, and so forth. and Cox and Raton are making cryptics for Games magazine and then these new young up and coming constructors are making them as well. So you can definitely trace a lineage going from those Sondheim puzzles all the way through this generation that's really popularizing American Cryptics.

Barry Joseph: That's an amazing history. Thank you, Ben. And then we have today, Katie, when you talk about going onto TikTok to teach it or teach them about Cryptics... which Cryptics are you solving? Who are making those? Where are you going?

Katie Grogg: It is not Sondheim. I felt like I was taking a big leap bringing Cryptics to TikTok. I'll go back just a second to say I would never have attempted Cryptics, if not for the livestream that I do. I also livestream on Twitch and we solve crosswords and as I said, I started out just doing regular crossword, which is what I was used to. And then the people in my chat. Ben being one of them would bring up like, Hey, you should try Cryptics, you should try Cryptics. And the first time I was introduced to them, I wanna say it was a Cox and Rathbone cryptic. Those were the names that kept coming up. So it's interesting that it has down and I attempted my first one, luckily with my chat in on Twitch to hold my hand.

And I felt like I was on the verge of tears as someone who considers themself a puzzle person and a good solver. I was like, I. I don't understand. I don't know what's going on. I'm so confused. I'll never get it. All the thoughts. And then after four years of a lot of practice and a lot of handholding, I now feel like I have graduated, like I said, my brain has stretched. I see things differently. I look at things new eyes. And so the things that I post about on TikTok to sort of like get my audience there to wade into the waters of Cryptics is called the Minute Cryptic. It's an Australian based company and they do, they have an app that they give one cryptic clue a day, which is pretty manageable. Just one cryptic clue. That's it. It's not a full grid. It's not, it's nothing too scary. And they'll give you hints. It is a very excellent resource for anyone trying to solve cryptics. It really breaks it down. It gives you that little sense of satisfaction when you get it, especially if you've gone days without getting it. And then you get one day where it just clicks. That is what keeps you going. That's what keeps the drive going. And that's what I've seen in my audience on TikTok. The my favorite comment to get is, oh my gosh, I got it before you. Like, I love to hear that. So exciting. So, yeah, , minute cryptic has been like the tool that, you know, I guess the trickle down effect has.

That's where it has gone nowadays.

Ben Zimmer: It's been gratifying to see Katie's progress, from when she was just working on, you know, American style crosswords on TikTok and Twitch. And then it was really her Twitch stream as she mentioned. There were several of us... another Ben named Ben Bass was really encouraging her to try out these cryptics you can do it, and being very encouraging and with help from the chat, figuring out all these little wordplay, gimmicks and things like that. And now she's a pro. She can do these without any help and continues to do it on Twitch. And so it is always fun to just sort of see someone open up a cryptic crossword for the first time and be like, what is even going on here? What are these clues? And it can seem so, uh, intimidating. But then little by little, um, you get the tools in your arsenal to figure out how to do them.

Barry Joseph: Let's wrap up today's episode with one final clip. This one is from Colm Malloy, who listeners to my podcast will know wrote the brilliant theme song to this very podcast, and in it he's building on some of what Richard Maltby Jr. Said earlier.

Colm Molloy: There is also wordplay going on, so it suggests something meta, but there's also a sense of.. A game lying underneath or a kind of challenge or there's. Again, it's like how in a good musical, the lyrics are saying one thing and the music is saying something else In a cryptic clue, you've got the clue saying something and the clue saying something else at the same time. And that's quite fun, that interplay. And I, I think it also makes one think about his psychology in that he clearly gets deep satisfaction from the tortured chaos of a crossword puzzle and trying to put it all into order somehow, I think. He talks about being dogged in terms of writing, and I think I can see that there is a torturous element to writing that is deeply unpleasant, but you do it because you know there's something worth it at the end. Even if that's just a grid filled, filled with words, there is something perversely satisfying about that. And you could say the same about musicals, I suppose.

Barry Joseph: So I wanna ask all of you, now that we've gone through this deep conversation about Sondheim and cryptic crosswords, how does your understanding of cryptic crosswords help you understand Stephen Sondheim and his work?

Natan Last: Yeah, I mean one of the things Sondheim ends up saying about all art is that it's about bringing order out of chaos. That formalism and organization of material is what making a puzzle is and what making a musical or a painting or a poem also is. And I think that there are sort of puzzly rhymes in Sondheim that helped me understand his cryptics and his cryptic clues helped me understand his rhymes. There's that line in Company where the words will sometimes spill over into the next bar. Like "it's spreading each minute through the whole vicinity". And the way that minute and vicinity are perfect, perfect rhymes, but not the full word of vicinity, I think is very cryptic in its playfulness. And it's just opened me up, I think, to the ways that musicals can, as we hear in the clip, be really beautiful, impactful, but can do many things at once, can be clever, can tickle different parts of the brain. And Sondheim, of course is the master of that.

Katie Grogg: I would offer that, starting with Sondheim as the musical genius and then finding the cryptic, content his puzzles galore... Solving his cryptics and seeing how many layers he goes with it and how it seems he could just keep going with the meta, like he could continue on forever. It's stunning to me that he was able to finish any composition ever. I'm like, I really am so impressed that he was able to stop him himself at a certain point and say, okay, this will be done now. Because I think he could have kept going eternity. And the genius would never stop.

Ben Zimmer: I would say that a recent experience really drove home the connection between Sondheim puzzles and Sondheim's musical theater career. And that was, getting to attend Katie Grogg's solo cabaret show, which she recently had in New York City. And Natan and I had the pleasure of attending that. The way that Katie weaved together these threads of, her obsession with crosswords and getting into cryptic crosswords, Sondheim plays a major role in, in Katie's production... as well as Maltby, right? Because the first number in Katie's show is kind of an adaptation of that Maltby number, crossword puzzle that he did for the, off-Broadway revue Staring Here, Starting Now, back in 1977. " I'm sitting here doing the Sunday Times crossword puzzle." So, seeing Katie put her own spin on all of that and sort of personalize that, was really just a wonderful experience of understanding how all these kind of threads come together.

Katie Grogg: Thanks, Ben.

Galen Fott: I would love a chance to see it. Absolutely. I was really struck at the end of Sondheim's book. Look, I made a hat. In the epilogue. He talks about this poem by Phyllis McGinley called Love Note to a playwright... , i couldn't find it anywhere online. I found it in a book and I posted it. The poem is about Richard Brinsley Sheridan. This is the poem that Phyllis McGinley wrote and how he had a habit of ignoring his mail. And instead, instead of the time that he spent, answering his mail, he was, first of all, of course, still a hugely celebrated playwright, but also a member of Parliament. That is what the poem is about. Tony Kushner would ask Sondheim to read this. There were a few events, I think, where Kushner asked question to Sondheim and Sondheim explained that he could not read it without crying, without it making him cry. If you read it, it's a wonderful poem, but there's nothing really inherently sad about it.

And what the poem is about is how you manage the finite amount of time you have. In my mind, I look at it this way, I think Sondheim decided to be married to musical theater. That was his spouse, but puzzles, boy, they were the tempting fling that was always right there waiting. You know.

Barry Joseph: Galen, thank you, Natan. Katie, Ben, thank you all for joining us today. If we wanna follow you or learn more about your work, where can we go?

Katie Grogg: I am coffee and crosswords on TikTok and YouTube and Twitch.

Natan Last: I'm @NatanLast on X and Blue Sky and Instagram. And my book Across the Universe is out now and available everywhere books are sold.

Ben Zimmer: I am, Ben Zimmer on Blue Sky and Facebook and some other places. Also benzimmer.com and yeah, you can look for my crossroad byline. Frequently in Slate and other venues.

Galen Fott: I'm just Galen Fott, G-A-L-E-N-F-O-T-T. I've got a few websites, my blog, which we've talked a good bit about, and then I'm an animator too. You can go to BigFott.com and see some of that if you want to.

Barry Joseph: Well, I think I'm now a little less intimidated by cryptics so thank you all once again. And I hope you dear listeners feel the same. In either case, thank you listeners for joining us for Matching Minds with Sondheim, the podcast. If you can't wait for the next episode to drop, then well please pick up a copy of my book, hit us up on the socials, Facebook and Instagram. And please comment and like the podcast on whatever platform you use. It helps us out immensely. I would also like to thank everyone who contributed behind the scenes to this episode.

The musical stingers composed by Mateo Chavez Lewis, our line producer Dennis Caouki, and the theme song to our podcast with lyrics and music by Colm Molloy, and sung by the one and only Ann Morrison, who created the role of Mary and Merrily we roll along. Until then, remember, someone is on your side... matching minds with Sondheim.

Ben Zimmer: I'm sitting here doing the Sunday Times crossword puzzle.