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The Results from the 14th ORCAS Awards!

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The ORCAS are the Oscars of the crossword community, dedicated to celebrating excellence in crosswords, and that was certainly the case during last night’s awards ceremony!

Clocking in at just under an hour, this was an event at breakneck speed, opening as all online award shows should: with technical difficulties.

David Kwong offered some anagram suggestions for other award shows and then passed the mic to Rich Proulx, whose bowtie game was ON POINT.

Rich’s intro was delightful, particularly when he shared that over $15,000 had been raised for the Trevor Project through the ORCAS puzzle packet!

With 97 people in attendance — including many nominees and puzzle luminaries in the chat — the first award was preceded by a tough trivia puzzle celebrating all of this year’s presenters:

After the solution was revealed, Ophira Eisenberg joined David in the hosting duties before inviting our first two guest presenters to handle BEST META CROSSWORD and BEST EASY CROSSWORD.

Aimee Lucido (author of Words Apart) read out the nominees for BEST META CROSSWORD.

I must confess that meta crosswords aren’t always my bag, but there’s no denying the skill and craftiness it takes to construct an effective meta. I ended up voting for “Blind Stitch” by Hanh Huynh because it felt like such a solidly constructed introduction to the concept of meta crosswords. It’s a great solve.

WINNER: Evan Birnholz for “Flying Colors”

“Queen of the Mondays” Lynn Lempel then read out the nominees for BEST EASY CROSSWORD.

Making easy crosswords is way tougher than it looks, and making easy crosswords that are still surprising and engaging is even harder. Despite that, this was a stacked category.

My vote went to Nate Cardin’s Untitled puzzle from the LA Times on February 25. Managing to find five phrases/compound words (OVERDRAFT, BODY WASH) where both parts could be followed by the word BOARD was an impressive feat of cruciverbalism.

WINNER: Jess Shulman for “Clear Up to Here?” (Lynn was the first presenter of the evening to do the “opening the envelope” gimmick for the winner.)

T Campbell and Laura Braunstein joined to present the next two categories.

Laura, one of the minds behind The Inkubator crossword, presented the EMERGING CONSTRUCTOR AWARD.

I sadly wasn’t familiar with all of the nominees in this category, so I had to go with someone whose puzzles I felt I’d had a good sampling of. My vote went to Carina da Rosa, whose work in Puzzmo and LilAVCX I’d enjoyed throughout the year.

And it turns out I wasn’t alone in my assessment!

WINNER: Carina da Rosa

T Campbell did a wonderful introduction about what separates BEST SUNDAY-SIZED CROSSWORD from the usual crossword fare before reading the nominees.

Despite the sheer ambition of “Just One Clue 2” and its crowd-sourced cluing, my vote came down to either the grid shape wordplay of Jonathan Raksin and Jeff Chen’s “Self-Starters” and the diabolic vocabulary in crosstina Aquafina and erik agard’s “themeless no. 36.”

I mean, we got SATAN WORSHIP and TWO CHEEKS OF THE SAME ASS, neither of which I’ve ever encountered in a grid. That being said, my deep affection for visual gimmicks in crosswords won out here.

WINNER: crosstina Aquafina and erik agard’s “themeless no. 36.”

Stella Zawistowski and Kim Vu were the next two guest presenters, with Stella handling BEST VARIETY CROSSWORD.

I love variety crosswords, because there are so many ways you can play with the traditional crossword formula to make something new and exciting. Rows Garden and Marching Bands puzzles are deviously designed masterpieces when constructed well, and this category showed off skill and cleverness in equal measure.

My vote went to a puzzle style I’d never seen before, as Ryan Faley’s “Nonplussed 4” combined across and down cluing with a non-traditional grid and a Rows Garden-style interior shape (pluses instead of blooms). I loved the construction and creativity, and the revealer was the cherry on top. Terrific stuff.

WINNER: joon pahk’s Two Outta Three Ain’t Bad

“joooooooooooooooooooooooooon” calls rang out both over the stream and in the chat to celebrate joon’s win.

Kim then read the nominees for BEST TOURNAMENT CROSSWORD.

Tournament puzzles are invariably bangers because they can push the difficulty AND creative envelopes, and this category was LOADED with heaps of cool ideas and challenges. (Last year’s Lollapuzzoola alone could have filled this entire category.)

The two puzzles that stuck with me the most were David Steinberg’s Westwords puzzle and Kareem Ayas’s Wild Discoveries puzzle from Lollapuzzoola. They were both wildly inventive, challenging, and above all else, memorable. This was the toughest choice of the entire ballot.

In the end, Kareem got my vote. And again, I wasn’t the only one impressed by his playful puzzling.

WINNER: Kareem Ayas for “Wild Discoveries”

A brief In Memoriam played next, offering tongue-in-cheek farewells to Deb Amlen (for ending her tenure with The New York Times), the Browser Crossword, and the free version of The New York Times Mini Crossword.

We then got a sincere send-off for influential creator and puzzle icon Mel Taub.

Our next two guest presenters were Peter Collins and Vic Fleming. They had a great little gimmick involving a swear jar and a virtual handover of $10 to celebrate the eventual winner of BEST CLUE (and my favorite of the nominated clues):

WINNER: [They might have “fuck you” money] for SWEAR JARS by Amie Walker and Amanda Rafkin, AVCX, April 18th

They next presented BEST THEMED CROSSWORD, which was another stacked category.

This category was a case of leading with your strongest contender, because Ada Nicolle blew me away with “Would You Let Me Finish” from Apple News+ on January 5th.

The grid is populated with longer entries that, when the last letters are removed, form the actual answers to the clues. So GOT THE ICK becomes GO-TH-IC, for example. It’s a great gimmick and a fun reveal when you get it.

WINNER: Untitled by Adam Wagner and Rebecca Goldstein

Rafael Musa, Ryan Fitzgerald, and Ben Gross then interrupted the proceedings for an interactive game with the audience. But first, they had a surprise award to hand out!

The Leviathan Award celebrates important contributions to the world of crosswords, so Ryan was blindsided by this award for creating the crossword software Ingrid. A video full of kind words from fellow constructors was played. It was heartwarming stuff.

Three instances of a puzzle game called Bracket City challenged the audience next. The goal was to unravel a series of crossword-style clues nested within each other, like so:

I doubt I was the first to solve this puzzle, but I was the first to post the solution in the chat: BLACK AND WHITE.

Work from the inside out with the brackets. [gun, as an engine] is REV, so you get [REVolving __] for DOOR, then [Friday with REVolving DOORbusters] for BLACK. [south of Spain] is SUR, so you get [flag raised in SURrender] for WHITE. BLACK AND WHITE is the final answer.

David and Ophira solved the first two puzzles live while the audience solved at home, and everyone was challenged to solve the third (and most complicated) bracket city puzzle in their free time. Can you unravel it?

David and Ophira continued the awards and presented the next category, BEST MIDI CROSSWORD.

As was the case with several categories, we were absolutely spoiled for choices when it came to midi crosswords. Crossword Gentleman Doug Peterson had a great one, we had ablaut reduplications from Alex Rossell Hayes, a tightly constructed foursome of BOOM-based entries from Amie Walker, and Peanuts grid art from franci dimitrovska.

But I had to go “By the Numbers” by Kaye Brown. The sheer ambition of a LOST-centric puzzle with character names reading across and aligning with the infamous numbers from the show. It’s a fantastic bit of constructing wizardry.

WINNER: Amie Walker for “Bangers”

Our next presenters were Brad Wilber and Mangesh Ghogre to handle the one-two punch of BEST CRYPTIC CROSSWORD and BEST VARIETY CRYPTIC CROSSWORD.

I have been on a quest to improve my cryptic crossword solving over the last few years, so the nominees in these two categories put me through my paces! The devious cluing was at its peak in the cryptics, and I think I spent more time on each cryptic than I did on any two or three of the puzzles in the other categories!

Amidst all the tough cluing and interesting vocabulary, it was Jamie Ding’s AVCX Cryptic and The Rackenfracker’s “High Definition” who got my votes this year.

WINNER, BEST CRYPTIC: PiGuyN for “pi guy cryptic 22”

WINNER, BEST VARIETY CRYPTIC: The Rackenfracker (JonMichael Rasmus & Sean Weitner) for “High Definition”

Our penultimate pair of guest presenters were Katie Grogg (looking glam!) and Jared Goudsmit. They presented the nominees and some great puns as well (and made a strong case for hosting next year’s awards).

The first award they presented was BEST CROSSWORD-RELATED MEDIA.

This is a new category for this year’s ORCAS, and as you can imagine, I was absolutely stoked to be included amidst a murderer’s row of excellent, insightful commentary on all things crosswords.

I quite selfishly voted for a PuzzCulture piece, as I was immensely proud of “The Curious Case of Richard Simon’s Aunt, Hedwig.” I didn’t expect to win, and was very content just for the opportunity for new eyes to find the blog.

WINNER: Adam Aaronson for “Square Theory”.

The chat was so chuffed for Adam, with several shouting out his post as eye-opening and game-changing. Congratulations Adam!

Katie and Jared then presented BEST CROSSWORD COMMENTARY.

I love the behind-the-curtain glimpses offered in columns like Rex Parker’s, Wordplay, and the LA Times Crossword Corner, many of whom have been commenting crosswords longer than some of the attendees have been making crosswords or solving them!

All of these nods are well-deserved — Deb and Malaika are brilliant, distinct voices in the crossworld — but it was “Malaika Handa and Stephen Lurie” by Renee Thomason that got my vote.

WINNER: Sally Hoelscher for “Terrors of the Deep”

Our final two awards were presented by Christina Iverson and the very dapper Andy Kravis. First up was BEST THEMELESS CROSSWORD.

This one was a three-horse race for me, with killer efforts by Paolo Pasco, guest host Christina, and Erik Agard, all chock-full of great vocabulary and ambitious crossings. I finally managed to narrow it to Erik’s August 18th New Yorker puzzle when it came to my vote, but really, any of these three would be worthy winners.

WINNER: Erik Agard’s August 18th New Yorker puzzle

Finally, it was time for CONSTRUCTOR OF THE YEAR.

I genuinely have no idea how you even narrow down nominations for this category, because there are SO MANY talented constructors. My shortlist would be 30 people deep, easy!

Each of the puzzles included in the Trevor Project Puzzle Pack represented the nominees well, but it was Rafael Musa and Adam Wagner’s puzzles that stuck with me the most. I loved the gimmick in Adam’s “Endless Loop,” but in the end, I went with Rafael Musa. Each time I saw that name in the byline, I knew I was guaranteed a terrific solve.

WINNER: Adam Wagner

Adam was there to accept and gave a very sweet speech, celebrating the welcoming crossword community and the support of his wife and family. Amazingly, he only started constructing in 2019!

You can’t complain about an award show that only takes up an hour of your time, especially when Oscar and Emmy broadcasts can last into the wee hours. And the crossword community is full of quirky, likable folks, so anytime you can get a bunch of them in a room (virtual or otherwise) together, you’re guaranteed a good time.

I thought it was a little weird that the games got more time than some of the categories, but this was my first ORCAS. Maybe that’s how the show usually goes!

Congratulations to all the winners! There were so many amazing puzzles published last year, and it was a pleasure to get to solve so many mind-bending, entertaining, and lovingly crafted cruciverbalist creations.

It was cool to see 5 out of my 15 selections get the nod (and a few other winners in my honorable mentions). And I’m already taking notes to contribute nominees to next year’s ORCAS!

What did you think of the ORCAS, fellow puzzler? Did your favorites win? Was there a puzzle you loved that you wish had gotten more of a spotlight?

Let me know in the comments section below. I’d love to hear from you!

Delving into the 2026 Boswords Winter Wondersolve Puzzles!

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Tuesday night was my first chance to sit down and try my hand at the puzzles from this year’s Winter Wondersolve event. Given the talent involved amongst the organizers and constructors — as well as the always-reliable puzzles featured in previous Boswords-hosted events — I had high expectations, and I was not disappointed.

So let’s put those puzzles under the microscope and see what’s what!

Warm-Up: Opening Kickoff by John Lieb

Perennial Boswords warm-up puzzle master Mr. Lieb delivers a terrific puzzle to knock any ring rust off of solvers with this 16×11 football-shaped grid.

With both teams competing in this year’s Super Bowl (as well as one team’s coach) in the grid, the theme is on point and the smart construction makes this puzzle so accessible. It’s a first-class starter for a day of solving.

My favorite clue was the double use of “Like a haunted house” for both SCARY and EERIE, especially since they were in mirrored spots in the grid.

Puzzle #1: French Twist by Pao Roy

The tournament proper launched with this 15x grid that relied on pronunciation as much as wordplay, adding an “eh” sound to established phrases, like PURE NONSENSE becoming PUREE NONSENSE or SNAIL MAIL becoming SNAIL MELEE.

I appreciate a puzzle that takes you out of the traditional solving experience, so the fact that I had to say each theme entry aloud to get the most out of the solve was great fun. Add in the tight construction and you’ve got a strong opener on your hands.

Interesting grid entries included THE FONZ, HARISSA, TUMBLR, and DEEP CUTS, and my favorite clue was “Only Rock & Roll Hall of Fame inductee to win a National Book Award (for her memoir “Just Kids”)” for PATTI SMITH. I learned something in this puzzle!

Puzzle #2: Pandora’s Box by Wendy L. Brandes

Puzzle #2 was only a half-step or so tougher than Puzzle #1, remaining very solver friendly while still peppered with some great vocabulary.

This 16×17 grid had a marvelous visual element, with some of the bad things contained in Pandora’s Box literally escaping from their rows and longer entries, so CIVIC ENGAGEMENT only read CIVNGAGEMENT, as the rest of VICE was spelled out in the circled letters above.

With HOPE remaining in the box in the final themed entry, this puzzle’s beautifully visual style nicely encapsulated the classic myth. My favorite puzzle of the day!

Interesting grid entries included STRIATED, ENRON, USER FEES, and AMATEURISH, and my favorite clue was “Name contained in a wedding registry?” for GREG.

Puzzle #3: Skipping a Grade by Adam Aaronson (or dm ronson, perhaps?)

The most devious puzzle of the day belongs to Adam Aaronson, as this 16×17 grid featured theme entries where all of the As have been removed from phrases, turning BLACKSABBATH into BLCKSBBTH. With six theme entries plus the revealer STRAIGHT A’S, this grid was packed!

And it’s hard to deny the absolute insanity of writing FLLLLLLLL for “Refrain in a Christmas carol.” An unforgettable puzzly moment, to be sure.

Interesting grid entries included BEAN BAG CHAIR, RIZZLER, I’LL SUE, and CULT HIT, and my favorite clue was “India is in its alphabet, but not in it” for NATO.

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Puzzle #4: Themeless by Amanda Rafkin and Amie Walker

The tournament concludes with the toughest puzzle of the day, a 15x themeless grid with an S-shaped grid pattern that created a genuine flow while solving.

Two sets of clues were offered for the final puzzle — FLURRY clues on the easier side (approximately a NYT Wednesday level) and BLIZZARD clues on the tougher side of the spectrum (approximately a NYT weekend level) — but both offered their fair share of challenges for solvers of all skill levels.

I have gained a new appreciation for themeless puzzles over the last few years (in no small part thanks to Boswords’s seasonal themeless leagues), and this one was a highlight, for sure. Great long entries, fun fill, and really smart construction made the final challenge of the day a very satisfying solve.

Interesting grid entries included WHITE LIE, STRAY CAT, SCRAP PAPER, TARGETED AD, and THERE THERE. Both the easier and tougher sets of clues had some gems, so I’ll list them separately below:

FLURRY clues:

  • “Brass fastener, as in a kid’s model skeleton” for BRAD (love the specificity!)
  • “Ball culture affirmative” for YAS
  • ‘”You can totally pull off a Mariah Carey song at karaoke tonight,’ probably” for WHITE LIE
  • “Wool whose name becomes a country if you change one letter” for ANGORA

BLIZZARD clues:

  • “Draft pick?” for SCRAP PAPER
  • “Twosome in ‘Waiting for Godot'” for ACTS
  • “Whopper Jr.?” for WHITE LIE
  • “It might be right up your alley” for STRAY CAT

This year’s tournament felt like the perfect introduction to tournament-style solving and puzzles for a newbie competitor, and the wide array of themes, cluing, and grid entry vocabulary kept me engaged throughout the entire solve.

The cluing this year was topnotch, and I laughed out loud several times at the clever linguistic trickery on display.

Boswords events aren’t about difficulty, they’re about the joy of crossword solving and wordplay and all the delights that come with filling in these black-and-white grids, and this year’s Winter Wondersolve was no exception.

It’s the right mix of challenge and creativity for solvers accustomed to NYT-style solving, and I think the constructors and organizers did one heck of a job putting together the event. A hearty tip-of-the-hat to the hardworking puzzlers for pulling this all off!

I can’t wait to see what they cook up for us next.

And speaking of, the Boswords 2026 Spring Themeless League is coming soon! A weekly tournament that happens every Monday night from 9-10 pm Eastern in March and April (with a bonus livestream hangout!), the Spring Themeless League is the kind of community puzzly joy that is always welcome.

Registration for the event opens Saturday, February 15th, and they’ve already announced a killer’s row of constructors (in addition to the spot for the winner of their open submission contest).

This year’s line-up includes Kareem Ayas, Michael Berg, Malaika Handa, Katie Hoody, Rafael Musa, Jess Shulman, Byron Walden, and Stella Zawistowski.

Check out the Boswords website for full details!

Thanks for solving with me today. Did you tackle the challenge of the Winter Wondersolve, or will you be participating in this year’s Spring Themeless League? Let me know in the comments section below, I’d love to hear from you!

Women of Letters (and Squares and Boxes and Clues and…)

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Puzzles bring joy to so many of us. They’re an escape, a challenge, a satisfying little test of our wits, our dedication, our creativity, and our flexibility of thought.

In uncertain times, in times of trouble, people often turn to puzzles. Puzzles were a refuge for many during lockdown when COVID hung over our heads. And now, when so much seems uncertain, if not downright unstable, people will no doubt turn to puzzles again.

That’s not to say that puzzle solving is a mere flight of fancy, a desperate bit of escapism, a Hail Mary avoidance of difficult circumstances, hard questions, and treacherous times to come. Quite the opposite, in fact.

If you turn to puzzles now, you’ll see a road map that proves things can get better.

Because, like it or not, misogyny once dominated the world of puzzles. It was baked into crosswords from the very beginning.

Yes, Arthur Wynne created the template for crosswords. Simon & Schuster are credited with publishing the first crossword puzzle book, as well as all the bestselling puzzle books that followed, serving as the foundation that helped build their brand.

But it was women who made crosswords into something more.

Women like Richard Simon’s aunt Wixie. She insisted Simon look into publishing a limited release crossword book. (UPDATE: I originally wrote that none of the stories mentioned her name, but I later found some that included her nickname, Wixie. I later discovered her actual name is Hedwig Simon.)

Women like Margaret Farrar. While serving as “an unofficial editor of the crossword-puzzle section,” she prevented errors and helped establish some of the baselines that still stand in crosswords today.

Women like Ruth Hale. Ruth was the founding president of the Amateur Cross Word Puzzle League of America, an organization that set crossword standards like limiting black squares and symmetrical grids, building off of Farrar’s work.

Women like Nancy Schuster. Schuster (no relation to the aforementioned publisher) not only ran Dell Crosswords but was the first winner of the American Crossword Puzzle Tournament.

Women like Helen Haven. In the 1920s, Haven was the organizer of the first competitive crossword-solving contest and served as the puzzle editor for The New York Herald-Tribune.

As pointed out by Anna Shechtman in her book The Riddles of the Sphinx: Inheriting the Feminist History of the Crossword Puzzle, between 1913 and the 1960s, most crosswords were created by women.

Puzzles were literally women’s work! With all the connotations that phrase invites.

And crosswords were derided as a frivolous pastime because of it. Not only because women made crosswords, but because crosswords were predominantly solved by women.

The New York Times called the crossword “a primitive form of mental exercise” and female solvers were blamed for neglecting their families and wifely duties because of their “utterly futile finding of words the letters of which will fit into a prearranged pattern, more or less complex.”

Funny how their opinions changed just in time to profit on crosswords in the 1940s.

Much like the Beatles — who were dismissed as nothing more than a glorified boy band when thousands of women cheered at their shows, only for them to be recognized as a once-in-a-generation group of talents when men started paying attention — crosswords became “respectable” only when men took interest and took over.

The percentage of female constructors published in The New York Times went down during the Will Shortz era, as compared to the Will Weng and Eugene Maleska eras.

And like it or not, but “the average solver” concept — a problem I discussed years ago — is still using a white male yardstick for comparisons, to the detrimental of solving and constructing.

In a wonderful blog post on the subject of women in puzzles, the author of the piece opens with the line “I’ve always associated crossword puzzles with men.”

And I realized how lucky I was to NOT have that association. In fact, I don’t think I would be a puzzly guy without the women in my life.

My mother (the first female store manager in A&P history) still solves crosswords and jigsaw puzzles to this day, and encouraged my interest in puzzles in the first place. My oldest sister (a teacher) introduced me to wordplay. My older sister spent hours playing puzzle video games like Dr. Mario with me. My younger sister is not just a master jigsaw puzzle solver, but a fiend at trivia nights and escape rooms, forever challenging me to match her flow.

I was trained in crossword puzzle editing and construction by Penny Press’s crossword guru Eileen Saunders, and still lean on her creativity and wisdom every day (and marvel at her blistering speed and efficiency).

I was shepherded through the world of variety puzzles by Los Angeles Times crossword editor and puzzle badass Patti Varol. (Though it was probably more like dragging my deadweight body through molasses than “shepherding” if I’m being honest.)

And that’s not counting the undeniable and indispensable influence of Amy Roth (a shining light at Penny Press), Chris Begley, and so many other female voices that make Penny Press one of the best outlets for puzzles in the world.

I love puzzles because of those women. I have made a career in puzzles because of those women. I am better at puzzles because of those women.

The puzzle world is better because of women. It will continue to advance and innovate and thrive because of women.

How do I know this? Because women are doing incredible things in puzzles RIGHT NOW.

A small sampling of the women making puzzles better. Wyna Liu, Amanda Rafkin, Soleil Saint-Cyr, Tracy Bennett. Illustrations by Ben Kirchner.

Look at The New York Times. Tracy Bennett, Wyna Liu, and Christina Iverson are delivering great daily puzzles like Connections, Strands, and Mini Crosswords not just consistently, but brilliantly.

The aforementioned Patti Varol is absolutely crushing it at The Los Angeles Times crossword. With Katie Hale and Angela Kinsella Olsen on Patti’s team, every month since mid-April 2022 has had a minimum of 50% women constructors and often exceeds that, all while delivering topnotch puzzles.

The New Yorker, USA Today, The Slate Crossword? Liz Maynes-Aminzade, Amanda Rafkin, Quiara Vasquez. Brooke Husic runs PuzzMo (where Rachel Fabi constructed my favorite puzzle of the year!) and Amy Reynaldo co-edits Crosswords With Friends.

Rebecca Goldstein just won the Orca for constructor of the year. Smarter people than me have called Stella Zawistowski a crossword boss in every sense of the word. Ada Nicolle won the 2024 Lollapuzzoola crossword tournament.

The impact of projects like Women of Letters and The Inkubator weren’t just the tip of the iceberg, they were the tip of the spear. A spear aimed directly at the heart of outdated notions of who makes crosswords and who solves them, dismantling the idea of some mythical “average solver” that has never truly represented the crossword audience.

As constructors, editors, and solvers, women in the past shaped puzzles as we know them. And women in the present are redefining puzzles. Not just in terms of representation (both as grid answers and creators behind the scenes), but in terms of acknowledgment, respect, and appreciation.

As for women of the future? I, for one, can’t wait to see what they have in store for us.

(And thank you to several of the women mentioned above for making this post far, far better than it started.)

Farewell, Stephen.

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[Image courtesy of Vanity Fair.]

Most people know him as a titan of Broadway and the American stage, the composer and lyricist behind dozens of iconic works, spanning decades. West Side Story. Gypsy. Into the Woods. A Funny Thing Happened on the Way to the Forum. (My personal favorite? Assassins.)

Even as someone with a degree in theater, I don’t feel qualified to discuss or summarize his impact on the stage. It’s monumental. Incalculable. Iconic.

But as a puzzle enthusiast, I do feel qualified to discuss his influence in that realm. You see, Stephen Sondheim occupies a curious space in the history of puzzles.

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He created cryptic / British-style crosswords for New York Magazine in the late 1960s, helping to introduce American audiences to that devious and challenging variety of crosswords.

In fact, he famously wrote an article in that very same magazine decrying the state of American crosswords and extolling the virtues of cryptic crosswords. (He even explained the different cluing tricks and offering examples for readers to unravel.)

Sondheim was an absolute puzzle fiend. His home was adorned with mechanical puzzles, and he happily created elaborate puzzle games. Some of them were featured in Games Magazine! In his later years, he was also an aficionado of escape rooms. (Friend of the blog Eric Berlin shared a wonderful anecdote about Sondheim here.)

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He also represents another link in the curious chain that seems to connect musicians with crosswords. Prominent constructors like Patrick Blindauer, Brian Cimmet, and Amanda Rafkin, as well as top crossword tournament competitors like Dan Feyer and Jon Delfin also have musical backgrounds.

In the crossword documentary Wordplay (and quoted from the article linked below), former New York Times Public Editor Daniel Okrent mentioned why he felt that musicians and mathematicians were good fits as crossword solvers:

Their ability to assimilate a lot of coded information instantly. In other words, a piano player like Jon Delfin, the greatest crossword player of our time, he sits down and he sees three staffs of music and he can instantly play it. He’s taken all those notes and absorbs what they mean, instantaneously. If you have that kind of mind, and you add it to it a wide range of information, and you can spell, you’d be a really great crossword puzzler.

Sondheim certainly fits the bill.

He will forever be remembered for his musical creations, and that legacy far overshadows his work in puzzles. But as someone who opened the door to a new brand of puzzle solving for many people, Sondheim will also have the undying loyalty, respect, and admiration of many puzzlers around the world.

We wholeheartedly include ourselves in that crowd of admirers.

Farewell, Stephen. Thank you.

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A Cracking Collection of Crossword Clues

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Someone recently asked me about my favorite crossword clue, and after mentioning four or five off the top of my head, I cut myself off and tried to explain that it’s impossible for me to pick one.

So many clues are out there that surprised me, or outwitted me, or made me laugh, or made me think in an unexpected way. I could never narrow it down..

Regular readers who have seen my reviews of various crossword tournament puzzles will recall I like to highlight favorite clues.

I actually keep track of clues from constructors as I solve various crosswords. Not only are they often witty, hilarious, and/or impressive, but they inspire me as a puzzler to always try to find entertaining, engaging new angles for these crucial crossword elements.

So today, I’d like to pull some favorites from my personal clue vault and give them some time in the spotlight.

(I’m crediting the constructor listed on the byline for each clue. These clues may have been created elsewhere and reused, created by the constructor, or changed by an editor, I have no way of knowing. So I’m just doing my best to give credit where credit is due.)

Misdirection

I love a good misdirection clue, because it not only has a straightforward meaning that sends you one way, but it has a true secondary meaning that usually only emerges once you’ve considered the clue for a bit.

Constructor Amanda Rafkin has a knack for these sorts of clues, delivering terrific examples with “Decline a raise?” for FOLD and “One who’s pro con?” for NERD.

It’s particularly great when a constructor can use a misdirection clue to put a new spin on a word you’ve seen dozens of times before. Peter Gordon did just that with both TYPO (“Character flaw?”) and AHS (“Sounds made with depressed tongues”), and even manages to be topical whilst doing so, as he did with the clue “Page with lines of dialogue” for ELLIOT.

Yacob Yonas took an awkward RE- word — all too common in crossword grids — and made it shine when he clued REHEM as “Take up again, say.” Priyanka Sethy did the same with a multi-word answer when she clued IGOTIT with the delightful “Catch phrase?”

Brendan Emmett Quigley covered up an ugly abbreviation answer — ECG — with a banger of a clue: “Ticker tape?”

As you can tell, misdirection clues are absolutely a favorite of mine.

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[Image courtesy of XKCD.]

I also can’t resist clues that get a little meta, playing with the format of cluing itself.

TYPO appears for a second time in today’s post, but the cluing is totally different, as Andrea Carla Michaels offered this meta treat: “Something annnoying about this clue but hopefully no others!”

And Francis Heaney went out of his way to word to clue the word AUTOMOBILES in a manner you’ll never forget: “‘Humorous People in ____ Acquiring Caffeinated Drinks’ (Jerry Seinfeld series whose name I might be remembering incorrectly)”

Using multiple examples in a clue not only shows off the variety of definitions some words have, but allows constructors to juxtapose these meanings in entertaining fashion.

Janie Smulyan deftly shows off this technique by cluing SPELLS “Some are dry, some are magic.” Concise and clever.

“Beehive part, or beehive parter” for COMB was Sid Sivakumar’s tricky way to use multiple meanings twice!

And although this Hannah Slovut offering isn’t as concise as the others in this clue for SEE, it’s still a terrific example of employing multiple uses of a word: “Different tense of ‘saw’ that may precede ‘saw'”

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[Image courtesy of David Louis Ghilchip.]

I know some crossword outlets aren’t fans of using clues that specifically reference each other — “With 21-Across, name of Charlie Chaplin film,” for instance — but other publishers are completely fine with this style of cluing.

Naturally, that allows constructors to have some fun making connections and using clues to reference each other.

Hannah Slovut utilized this technique in a recent puzzle, cluing STYE as “Ailment that might be seen near 63-Across.” (63-Across was the exclamation MYEYE.)

There are all sorts of cluing styles we didn’t cover in this post — trivia clues, fill-in-the-blank, clues that use capitalization or pronunciation to mislead the solver — but hopefully we’ll get to them in a future blog post.

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In the meantime, how about a few more misdirection clues for the road?

Brooke Husic made readers take a second look at a familiar word — “Surroundings?” — when she used it to clue SIEGES.

Catherine Cetta’s “Spot early on?” definitely sends you down the wrong path before you double-back and find the correct answer: PUP.

And we happily conclude with a clue from puzzle master Mike Shenk, who clearly had some fun with this one, cluing ANKLES with “They’re just over two feet.” Absolutely shameless.

Gotta love it.

What are some of your favorite crossword clues, fellow puzzlers and PuzzleNationers? Let us know in the comments section below! We’d love to hear from you.

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Delving into the Lollapuzzoola 14 Puzzles!

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The fourteenth edition of Lollapuzzoola, as is tradition, arrived on a Saturday in August, but for the second year in a row, it was hosted online to allow tournament solving from home.

I was not in virtual attendance, but I did sign up for the Next Day Division puzzle packet. Last weekend, I finally had a chance to sit down and try my hands at this year’s tournament puzzles, and I was not disappointed. Lollapuzzoola continues to push the envelope with inventive themes and unique spins on how to bring crosswords to life.

This year’s theme was “This Time, It’s Virtual… Again.” Every puzzle had something to do with social media, social distancing, or some other aspect of virtual life that emerged during the pandemic, and the constructors were clearly inspired in all sorts of ways. Let’s take a look at what they came up with.

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Two rehearsal puzzles served as a warm-up for this year’s tournament crosswords. The first was constructed by Brooke Husic and Sid Sivakumar and entitled “Hit Me Up!” This puzzle immediately reminded solvers that anything could happen at Lollapuzzoola.

Not only were the theme entries reading down — which isn’t that weird, but it’s fairly uncommon — but there were animated GIFs as clues for three of the answers. The theme was fairly accessible: phrases that started off with a method of communication like ZOOM or TEXT, confirmed by the revealer CONTACT HIGH (since the method of contact was the highest part of the down entry). All in all, a puzzle with a solid hook, complimented by good grid fill. Exactly what you want from a warm-up.

The second rehearsal puzzle was constructed by the same duo (but with Sid leading off the byline this time) and entitled “Box Score.”

This was a strong follow-up, featuring the word WIN as a rebus-style single-box entry, which allowed for some devious crossings (like ENTWINE crossing RAW INGREDIENTS). The fill was smooth and I learned that KOREA is the home of the Baekdu-daegan mountains. Neat!

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Puzzle 1: Extremely Casual Friday by Robyn Weintraub

The tournament puzzles kicked off with this enjoyable opener, a 15x grid with clean fill and quite the appropriate theme for a virtual tournament.

Each theme entry was a phrase starting with a type of pants — SWEAT, PAJAMA, YOGA, and hilariously, NO — tied together with the answer word PANTS in the bottom-right corner.

Well constructed, humorous, and a great solve… it’s the recipe for an ideal Lollapuzzoola puzzle #1.

Interesting grid entries included REPLY ALL, SLOPPY JOES, and BEST BET, and my favorite clue was “This puzzle was constructed by Brooke Husic, e.g.” for LIE.

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[Here, Deb Amlen (blue checkmark and all) demonstrates Twitter tagging.]

Puzzle 2: Tag! by Amanda Rafkin

This 17x puzzle embraced the social media theme by embedding @ symbols in the grid as starters for the theme entries (where @ represented AT, like in @ASTANDSTILL), allowing for some fun crossings.

The theme was encouraged further by the revealer TWITTER MENTIONS, as well as a blue checkmark next to Amanda’s byline. (For the uninitiated, the blue checkmark, aka the blue tick, is used on Twitter to indicate someone is a verified user. It’s often a source of some small social media clout as well.)

With strong fill and some signature Rafkin flare — it’s very Amanda to have a Sondheim reference — this was a great confidence-building solve with a heap of style. I quite enjoyed this puzzle.

Interesting grid entries included AW NUTS, EYE DOC, and STAYED INSIDE, and my favorite clue was “Sound that might drown out some $%!#ing bad words” for BLEEP.

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Puzzle 3: Get the Message by Sid Sivakumar

This 19x grid with vertical symmetry was a definite step-up in difficulty after the first two puzzles, but it’s also a strong puzzle with a great design.

The theme for this one involved chat/texting slang like TTYL and ROFL, and like the second rehearsal puzzle, it had a rebus element where those abbreviations were contained in a single box, used by two crossing entries. This was supported not only by the cluing — which included a fake username and comment to indicate some chat or textspeak was involved — but the revealer CHATBOX in the middle of the grid.

I probably wouldn’t have realized as quickly that there was a rebus involved if I hadn’t had rebuses on the brain after solving the rehearsal puzzles. But even without all hints, this was a fairly tight grid that made the most of its theme. (I wasn’t a huge fan of IN appearing three times in the grid, but that might be seen as a nitpick.)

Interesting grid entries included PRESS KIT, SASHAY AWAY, SIERRA MIST, and EVIL ONE, and my favorite clue was “Bar, barn, or barrel” for UNIT.

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Puzzle 4: Connecting… by Brooke Husic

Okay, here we go.

Puzzle 4 was a 15x grid with one doozy of a gimmick. Most of the down clues were replaced with an animated GIF of three dots moving (like the one above), the instantly-recognizable image of a message either being typed or incoming, but that hasn’t arrived yet. (For Next Day Division solvers, there was no animation, just three dots, but the message was still clear.)

All the across clues were still there, and SOME of the down clues as well. The remaining down clues were long, and almost felt like the clues from a cryptic or British-style crossword, because they didn’t seem to quite fit the answers in the grid.

I can only imagine the baffled terror I would have felt in the moment during the tournament if I tackled this puzzle live. I imagine it would have been similar to this poor soul’s experience:

tim pierce

Thankfully, I finally realized what was going on. The down clues weren’t just for their particular coordinate, they were for all of the words in that column. For instance, 55-Down was clued “A+ hosts,” and the answer to 55-Down was MCS. That could fit. But only “hosts” applied to 55-Down. “A” and “+” were the clues for the two down entries above 55-Down: 1-Down ALPHA and 32-Down AND.

Across-only solvers probably got farther than most with this one at the start, and I can imagine the grid would feel almost impenetrable if you didn’t figure out the gimmick.

But man, this is clever as hell and a solving experience nobody is going to forget anytime soon.

Interesting grid entries included HIGGS, OPEN SECRET, and SVELTE, and my favorite clue was either “A+ hosts,” as listed above, or “Get the picture SO much” because “SO” clued BOO and I thought the misdirect was very clever.

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Puzzle 5: You’re Muted by Patti Varol

After a brain-melter like Puzzle 4, Puzzle 5 was clearly designed as a cool-down puzzle before the tournament final. And I’m sure it served that purpose amiably for many solvers.

But for some reason, this theme took me the longest to get, and I felt so dumb when I realized how obvious it was.

This 21x grid featured theme entries where part of the phrase that sounded like “You’re” had been removed. For instance, JUNIOR EXECUTIVES became JUNE EXECUTIVES, and VEGETABLE PUREE became VEGETABLE PAY.

For some reason, the sound aspect of it just blew past me several times on the way to the forum, and I was done with the grid for MINUTES before it finally dawned on me. Patti is going to be so disappointed with me.

The theme is terrific and the grid fill is solid. This was a great capper for the tournament proper, helping bring (most) solvers back down to earth after the whirlwind that was Puzzle 4.

Interesting grid entries included SNIVEL, SINEWED, MOONSTRUCK, PHOTOBOMB, and ALL TIME LOW, and my favorite clues were “Dirt pie ingredient” for OREO and “Notable Ford of the 1970s” for GERALD.

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[The tournament finals, live on Twitch!]

Puzzle 6: Finals by Wyna Liu

As always, there were two sets of clues for the Finals puzzle, the Local and the more difficult Express clues. No matter which clues you were working with, you were in for a terrific tournament finale.

This themeless 15x was tough but engaging, featuring lots of long entries and unusual phrases crossing, making for a satisfyingly challenge finale and a suitable final boss for the top contenders. The entry NHL MVP tripped me up more than once, what a brutal combination of letters, but the tight grid and strong cluing for both the Local and Express solvers made this an excellent wrap-up to a great day of puzzling

Interesting grid entries included CRAFT VODKA, THE ROYAL WE, “I’M NOT A CAT” (referencing that amazing online legal proceeding debacle), ACID ROCK, Y-AXES, and LEO X. Both the Local and Express sets of clues had some gems, so I’ll list them separately below:

Local clues:

  • “Saved butt” for ROACH
  • “Ah, this is the life (to Mario and Luigi)!” for ONE-UP
  • “Ones for the books?” for SCHOLARS
  • “Moving parts of a painting on ‘Scooby-Doo'” for EYES

Express clues:

  • “What might require a blunt instrument?” for ROACH
  • “Congress, after adjourning?” for BREAKUPSEX
  • “Video game life form?” for ONE-UP
  • “Cabs, e.g.” for REDS
  • “Whence a popular countdown in Times Sq.” for TRL

There was also a tiebreaker themeless mini by Nam Jin Yoon. The mini was a quick and satisfying solve, anchored around the grid-spanning entries GATECRASHER and READ THE ROOM. Loaded with great vocabulary, this puzzle offered a nice wind-down after a strong tournament and several really engaging puzzles.

Interesting grid entries included RAHRAH and TOO SOON, and my favorite clue from the mini was “Some fishy characters?” for MERMEN.

[There was also a meta-puzzle suite AND a collection of ten mini-crosswords dubbed the Mid-Day Mini Meta which was constructed by a small army of strong up-and-coming constructors, both of which are absolutely worth your time.]

The puzzles at Lollapuzzoola always impress, and this year was no exception. The grids were neatly constructed, there was little crosswordese, and the creative themes, grid designs, clues, and puzzle mechanics ensured that not only would fun be had by all, but that the puzzles would linger in your memory. Especially Puzzle 4.

The puzzles were varied and engaging, and the Next Day Division solving experience is always a treat. Congratulations on the competitors and the organizers who made it all happen, especially in a virtual format with so many additional solvers. (Click here to check out the Twitch feed of the entire tournament!)

Lollapuzzoola is only getting more creative, more groundbreaking, and more clever with each passing year, and it’s just awesome to watch it grow and evolve.

I can’t wait to see what they come up with next year!

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