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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