5 Questions with Comedian, Animal Activist, and Puzzler Elayne Boosler!

Welcome to 5 Questions, our recurring interview series where we reach out to puzzle constructors, game designers, writers, filmmakers, musicians, artists, and puzzle enthusiasts from all walks of life!

It’s all about exploring the vast and intriguing puzzle community by talking to those who make puzzles and those who enjoy them! (Click here to check out previous editions of 5 Questions!)

And I’m excited to welcome Elayne Boosler as our latest 5 Questions interviewee!

If you haven’t heard of Elayne Boosler from her decades-long stand-up career — including being named one of Comedy Central’s Top 100 Comedians of All Time — you’ve certainly seen her work in radio, television, movies, and print. Elayne is a triple threat — comedian, actress, writer — and the founder of Tails of Joy, a non-profit organization dedicated to rescuing and caring for animals.

She became a quadruple threat last year when she added her first New York Times crossword to her accolades in a collaboration with constructor Patrick Merrell. (Of course, she’s also appeared as an answer in the NYT crossword over 30 times. In her words, “Yes, it’s cool. But one day when I’m really famous, I’m going to be 18 Down, and then 22 Across is going to say, “See 18 Down”.)

Elayne was gracious enough to take some time out to talk to us, so without further ado, let’s get to the interview!


5 Questions for Elayne Boosler

1. How did you first get into puzzles?

I’ve always had a touch of dysgraphia/dyslexia; my cursive writing (as they called it back in the 1800s) was always illegible, and when banks still checked signatures on checks I’d get about five calls a day. “But they are written on the same day, three checks in a row, and the signatures don’t match at all.” I know. I can read and write upside down and backwards. I remember driving in the car with my parents when I was really little, and reading a sign. I said, “Bar. R-A-B. Bar.” I can also sing any song you can throw at me, backwards, which once saved my life when I went to a school to talk to twelve-year-olds. I guess wordplay was the natural next step.

2. Now that you’ve made a New York Times-level crossword of your own, what was the most surprising part of the process for you? What did you enjoy?

I never passed any year of math in my entire life, and basically, making a crossword is math. The gentleman I made the puzzle with, Patrick Merrell, was a saint. If they threw some hyperactive puppy at me who thought she knew how comedy worked and said, “Write comedy together!”, and she emailed useless things to me three times a day, I’d kill her. Patrick was an unbelievably patient, wonderful, and talented teacher.

Though I’ve done crosswords all my life, as a layperson I never got the nuance of just how specific the theme clues have to be. It was mind-boggling. I think I sent Patrick clues and answers for a full month before he finally got to spell “water” in my hand. As an added bonus, Patrick wasn’t just brilliant about the words, he’s a crossword artist. His desire for grid symmetry and beauty was fascinating. I enjoyed all of it. Even the frustration.

Do you ever see yourself collaborating on or constructing another crossword?

I would love to collaborate on another puzzle. As you can imagine, after several months of thinking of nothing but themes, clues, and answers, I could not just turn my “crossword mind” off. So I have a LOT of lists of themes, clues, and answers, and I hope I get another opportunity to use them.

3. Many people know you from your trailblazing stand-up comedy career, or your appearances on shows like Night Court. But these days, you’re more synonymous with your charity work protecting animals. How did you get started with Tails of Joy?

I’ve always loved animals. I always knew I wanted to be a rescuer. Being on the road for forty-six years, I got to meet lots of rescuers in different states, and looked for a way I could have the most impact. What I learned was, three old ladies in Ohio will save more cats and dogs in a year than the entire bloated, overgrown Humane Society of the United States (HSUS) which has $300 million and is NOT a rescue organization! I knew the “little guys” needed someone to keep them from falling through the cracks.

So I founded Tails of Joy twenty years ago, and that’s what we do. We’re a nationwide and beyond, all animal (dogs, cats, birds, reptiles, sea life, wildlife, snakes, bunnies, big cats, primates, elephants, bears, everybody!!) rescue and advocacy group, which provides “Little Guy Grants” to the smallest, neediest rescue groups or individuals all across the country. If you’re reading this and you need help with an animal, contact us! All my money goes there. Every time a dog walks by my husband says, “There goes our beach house.”

4. What’s next for Elayne Boosler?

Thanks for asking. I have a boxed set of four of my specials, plus a new CD — Timeless — coming out on Comedy Dynamics on August 31st. I’m featured in the new season of “CNN’s History of Comedy”, Sunday nights at 10pm, and I’m featured in HBO’s new documentary, “Robin Williams: Come Inside My Mind”. I have a new piece up at CNN.com, “Elayne Boosler: Saying ‘Joke’ is no Excuse for Offensive Behavior.” And I spend hours every day doing rescue.

5. If you could give the readers, writers, and puzzle fans in the audience one piece of advice, what would it be?

I’m sure they already know this. When you look at a puzzle and you can’t fill in even one word, and you walk away, you come back later and sit down and fill it all in in five minutes. What does that tell you? The subconscious is always working, it’s always carrying out your directives, conscious or not.

So it’s very important to always try to speak in the positive, because you are actually giving your brain orders. In comedy, I have never said “I killed” or “I died”. I don’t say that. If you want to remember your keys, don’t say “I hope I don’t forget my keys”, because your mind hears “forget my keys”. You have to say, “I hope I remember my keys”. In essence, the subconscious has no sense of humor, so be careful how you program it.


A huge thank you to Elayne for her time. You can follow her on Twitter (or visit her website, Elayneboosler.com) for updates on her many MANY ongoing projects, and be sure to visit Tails of Joy to explore all of the wonderful work she does for animals.

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The New York Times Crossword, Accordion to Weird Al

 In February of 2017, The New York Times celebrated a landmark in the history of puzzles: the 75th anniversary of the NYT crossword.

And ever since, to commemorate that puzzly milestone, top constructors and Times favorites have been pairing up with celebrity fans and puzzle enthusiasts to co-construct puzzles for the Times!

This year, you might’ve encountered some of these collaborations, like news pundit Rachel Maddow’s March 2nd puzzle with constructor Joe DiPietro, or “How I Met Your Mother” star Josh Radner’s meditation-themed puzzler from January 31st with constructor Jeff Chen.

Over the last year, names as diverse as John Lithgow, Elayne Boosler, Joy Behar, Mike Selinker, Lisa Loeb, Neil deGrasse Tyson, and Bill Clinton have contributed their puzzly efforts to this marvelous project.

And yesterday, another famous wordsmith and master of punnery made his New York Times debut.

[Image courtesy of Instagram.]

Yes, the immortal “Weird Al” Yankovic teamed up with Puzzle Your Kids mastermind and friend of the blog Eric Berlin for a cheese-themed Wednesday outing that delighted fans and solvers alike.

Al has certainly been keeping busy lately, launching his Ridiculously Self-Indulgent, Ill-Advised Vanity Tour — his words, not mine; I loved the show I attended! — and working with Lin-Manuel Miranda to create The Hamilton Polka, an ambitious and hilarious take on the wildly successful musical.

The puzzle was Eric’s 40th Times puzzle, and Al’s first. Not only did the puzzle feature those signature cinematic cheese puns — like A FEW GOUDA MEN and THE PELICAN BRIE — but there was plenty of nerd culture featured in the fill and cluing.

Tom Lehrer and John Cleese were both name-dropped, as well as Legolas, Wile E. Coyote, WALL-E, Mr. Clean, and Bones from the original Star Trek.

Eric offered some insight into the puzzle’s creation while discussing the puzzle with Wordplay’s Deb Amlen:

My very first attempt at the grid included one of my favorites from his list, QUESOBLANCA. I was under the misapprehension that queso is not just the Spanish word for cheese but also a specific kind of cheese. Whoops, not quite. (This was entirely on me, I should note — Al, not knowing during his brainstorming that the end result would be restricted to specific cheeses, had several cheese-adjacent puns in his list, including FONDUE THE RIGHT THING and CHEESY RIDER.)

And appropriately enough, Al had a bit of fun promoting the puzzle on his Instagram, claiming, “If you’re REALLY good, you don’t NEED the clues!”

For the record, I needed the clues.


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Celebrity Constructors Galore!

[Bill Clinton enjoys a puzzle and a snack. Image courtesy of The New York Times.]

The New York Times Crossword celebrated 75 years of puzzles back in February, and ever since, they’ve been commemorating that puzzly milestone with a series of collaborations between established constructors and celebrity guests to create special monthly puzzles.

It started on February 15th, the 75th anniversary, with a collaboration by Patrick Blindauer and actor Jesse Eisenberg offering some food for thought with culinary wordplay.

On March 20th, astronomer and affable Pluto slayer Neil deGrasse Tyson joined Andrea Carla Michaels in creating a punny look at the stars.

Classical pianist Emanuel Ax teamed up with Brad Wilber to pen a music-minded puzzler on April 19th.

None other than former president Bill Clinton tried his hand at creating a crossword alongside judge and constructor Victor Fleming for the May 12th edition of the puzzle.

Tuesday, June 6th saw musician Lisa Loeb duet with crossword gentleman and friend of the blog Doug Peterson. Their theme involved concealing one-word #1 hit songs (including one of Loeb’s!) in larger phrases, leading to a Rihanna reference with UMBRELLAPOLICY, for instance.

And big names continue to appear.

Comedian and Tails of Joy pet advocate Elayne Boosler teamed up with Patrick Merrell for the July 12th puzzle, where they did modern day versions of classic films. For instance, Taxi Driver became UBERDRIVER and Holiday Inn became HOLIDAYAIRBNB. It was an excellent collab that made the most of Merrell’s gift of grid fill and Boosler’s wit and wordplay.

Clothing designer and television host Isaac Mizrahi joined forces with constructor David J. Kahn for the July 30th puzzle, employing crafty clues to put a spin on DIY construction phrases like “Cut and dried” and “On pins and needles.”

Tying a given puzzle’s theme to the guest constructor has been a recurring theme with the 75th anniversary puzzles, and the duo of Mizrahi/Kahn produced arguably the best examples thus far this year.

Most recently, constructor David Steinberg paired off with host, comedian, magician, and performer Neil Patrick Harris for the August 24th edition of the puzzle. Their magic-themed puzzle not only incorporated different parts of a standard magic show, but it concealed the name of a famous magician by hiding him among the down answers. (Or it would have, if he hadn’t escaped!)

Brilliant execution makes for a clever puzzle that Jeff Chen of XWordInfo declared one of his favorite puzzles of the year. (Of course, readers of the blog shouldn’t be surprised after solving the crossword Neil included in his autobiography.)

With more celebrity constructors still to come, including “a venerable TV journalist, a morning TV host, a six-time Emmy-winning actor, and a sitting U.S. senator, among others” (according to Will Shortz), I am definitely looking forward to seeing what other tricks these constructor/celeb duos have up their sleeves.


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