Jack Handey, Humor Writer and Comedy Legend

Jack Handey is an American humorist and comedy legend. He’s famous for his writing at Saturday Night Live, where he created “Deep Thoughts, by Jack Handey,” as well as famous sketches such as “Unfrozen Cavemen Lawyer” and “Toonces the Driving Cat.”

Jack Handey went on to write numerous humor books, including the Deep Thoughts series, What I’d Say to the Martians, and The Stench of Honolulu. He has been a frequent contributor to The New Yorker’s Shouts and Murmurs since the 1990s.

Jack has just published My Funny Cowboy Dance, a new collection of hilarious short humor pieces from from The New Yorker, Outside, and elsewhere, plus nine TV sketches from “Saturday Night Live,” and 22 new Deep Thoughts.

This conversation with Jack Handey explores the humor in My Funny Cowboy Dance, plus some timeless tips for how humorists can sharpen their craft!

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ALEX BAIA: My Funny Cowboy Dance opens with “Hydrogen Car,” a piece about exploding hydrogen cars. How did you decide to open with that one? Is this just you following the time-honored advice to “open with a bang?” 

JACK HANDEY: A reader mentioned that he thought it was the funniest of my then-recent pieces.  And who am I to argue with an anonymous reader?  I do think it’s a strong piece though, and not from The New Yorker, which adds to the variety.

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How did you choose the sequence for this collection? And how do you generally approach sequencing a book that collects shorter pieces? I see on the back of the book there’s a picture of note cards on a bulletin board, so I’m guessing that was a part of the process.

Yes, I’m a believer in the note-card-on-bulletin-board system.  I guess I got it from my Saturday Night Live days. The cards help you keep pieces with similar themes away from each other (Martians, grisly death, etc.)  Also they help you see the book as a whole, with a couple of strong pieces followed by a softer piece, etc.

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A few pieces in my My Funny Cowboy Dance feel more like short stories, e.g. “Apocalypse” and “Toothpick.” Do you think you might lean into more short story writing in the future?  

I am coming to find narrative pieces, like my novel The Stench of Honolulu, more fun to write.  I think it’s because the story requires a certain type of joke, rather than the premise — if that makes any sense.  It’s challenging.

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Let’s get into some humor writing geek questions. I’m curious about how you self-edit. When you have a first draft of a humor piece, what kinds of self-editing are you doing to improve the draft into something final and publishable?

Often, cutting is the best answer.

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Do you have any tips on sentence-level joke writing for humor pieces? How can writers make their individual jokes shine in a humor piece?

Try your jokes out on someone whose opinion you trust.  Also, don’t make a joke too “sweaty” — that is, too long and convoluted. A good joke has a certain non-logic.  It’s often mathematical, as in “2 plus 2 = 5."

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Comedy has few if any “rules,” but one that people sometimes reference is, “the funny thing goes at the end.” You can see this pretty clearly in stand-up comedy. Is this a useful “rule” in humor writing? 

Yes, in a joke, usually the key word comes at the end.  But sometimes an average line can be hilarious if it comes in the midst of a totally ridiculous situation.  Those are usually the best.

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What are the most common ways you find humor premise ideas? Or, putting it another way: What are the circumstances in life where humor premise ideas pop into your head?

In my experience, a good idea will occasionally pop into your head, but that’s uncommon.  Usually it takes lying on a couch or the floor and free-associating until you come up with an idea.  You write it down, then come up with some more.  Then you go back through them and see if any are funny.  My friend, screenwriter Fred Wolf, used to say that if something was funny after three days, it was funny.

One thing that oddly seems to help generate ideas is heat.  A warm bath or shower.  Or pulling a blanket over yourself while you’re lying on the couch.  Of course, if you’re crawling through a hot desert, looking for water, you’re probably not going to come up with a good joke.

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If a humorist has a list of premise or piece ideas, how do you recommend they go about selecting one to draft? 

Basically, if it seems funny.  Also, if it seems to invite several jokes that fulfill the premise.

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Do you have many premise ideas for humor pieces that go unused? Or premise ideas that get turned into first drafts, but you don’t like the draft enough to see it through?

I have folders full of bad ideas and weak drafts.  They don’t get better over time.  Sometimes you can trick yourself into believing an old idea is pretty good, but usually it’s not.  I recently went through my Deep Thoughts, originally typed on 3x5 cards, and weeded out 2,000 weak ones.  I burned them in my fireplace.

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As a humorist, sometimes I’ll finish a draft and think, “hmmm, not my best work.” Or, maybe the piece will get rejected. How should humor writers proceed? When should we push on and try to publish it somewhere else versus just throwing the piece away and moving on?

If you’re a young writer, send it back out.  You want to get published.  But sometimes being proud of getting published can bite you.  When I was young and had a humor piece come out in Oui magazine, I sent a copy to my parents.  But it also had several photos of unabashedly naked young women.  Yikes!  

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Do you have examples of pieces where you’ve had to make a big shift—like a shift in the premise or format—to make it work? I read in another interview that your New Yorker piece, “Guards’ Complaints About Spartacus” was originally about the Man in the Iron Mask. These kinds of shifts are interesting because they show that it’s fine to let an idea evolve.

Good question.  Sometimes you’ll have an idea, but it doesn’t quite click.  You let it simmer in your head.  (Your brain likes to work on unfinished ideas, especially when you’re asleep.)  

Many times the answer is to push it farther.  When I came up with the idea for the sketch “Unfrozen Cave Man Lawyer” on SNL, at first the idea was that they find a frozen cave man, but they accidentally melt him.  Or they find way too many frozen cave men.  Finally I decided on one cave man, but it wasn’t enough. What if he’s a sleazy lawyer, playing on his caveman roots?

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Do you have any tips for how humorists can steadily improve their craft over time?

The most important thing is to find your own voice.  For me, it took writing many, many pieces that anyone could have written, before finding a certain attitude.

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Do you have any personal favorite pieces in my My Funny Cowboy Dance? 

Good question.  I lean toward the darker, mean-spirited things.  I think John Cleese said that to a comedy writer, a man slipping on a banana peel isn’t that funny.  It has to be an old woman falling into a manhole.  So I like “Execution Days” and “The Mysteries of Humor.” Also “Message to my Clone,” because it’s so cruel.  I also like stupid, as in “The Symbols on My Flag." 

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It feels like a lot of your recent humor-writing career has been building up to My Funny Cowboy Dance. Now that it’s out there, do you think you’ll retire the Funny Cowboy Dance? Maybe pick a new type of dance? Or is this simply a dance that cannot be retired?

The funny cowboy dance will live forever!

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Get My Funny Cowboy Dance, by Jack Handey, exclusively from deepthoughtsbyjackhandey.com.

Want to write humor? Get The Ultimate Humor Writing Cheat Sheet: my tips and tricks for writing funnier stuff and publishing humor in The New Yorker, McSweeney’s, and Slackjaw.