Opinion | Anthony Flint

Dying is easy. Comedy is hard. Stand-up comedy? Harder

Microphone over the Abstract blurred photo of conference hall or seminar room background.
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What’s up with all these people around Boston taking stand-up comedy classes? Am I right?

Just about every nightfall in Central Square, the faithful report to ImprovBoston for two-hour workshops, from college students to working professionals to retirees. And they’re not necessarily thinking they’ll become the next Jerry Seinfeld.

For me, taking ImprovBoston’s eight-week “Intro to Standup” course was part fifty-something bucket list, part dare, and part professional development. I consider myself a student of comedy, appreciating technique and craft, whether Ellen DeGeneres or Super Bowl commercials. I thought maybe I could pierce the veil. I also knew that corporations, nonprofits, doctors, and lawyers — and even some politicians, I’m told — have begun to understand how comedy training, particularly improv, can lead to better communication and workplace collaboration. Who knows, maybe it would make me a more astute writer and public speaker. Or at least give better toasts.


Here’s what I learned: As much as I want to be funny naturally, comedy is serious business. It’s hard work. Virtually everything a comic says on stage has been tested, vetted, edited, scripted, and assiduously rehearsed. Even as they make it seem like they’re saying it for the first time.

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Another revelation is how comedy marvelously transcends culture, and exacerbates our many tensions, all at the same time. One of the first things I did was make a ham-handed reference to the misconduct that continues to make headlines. Louis C.K. apologized and Larry David bombed on Saturday Night Live around the fourth week of class, prompting an hour-long discussion about what’s funny, and what’s beyond the pale.

The ladies and gentlemen filing into the studio every Wednesday — under the tutelage of comedian Kelly MacFarland — included a retired teacher, an executive from Harley-Davidson, an Emerson College student, a lawyer specializing in regulatory compliance who was recovering from a brain injury, an art history professor, a leadership consultant, and a PhD candidate in economics at Harvard.

One after the other, we’d get up on stage, and get down to the business of bombing. Our goal was to “find the funny.” By the seventh week, I announced that I had looked everywhere, but I just couldn’t find it. “Hey, that’s funny,” the leadership consultant remarked.

The whole thing is preposterous. What makes anybody think they can do this coming in off the street, any more than start to play the cello like Yo-Yo Ma? True, there are classes for all kinds of things — painting, cooking, dancing, writing. Watch HGTV enough and you can probably do a decent job transforming a fixer-upper.


But being a stand-up comic — what Seinfeld describes as showing up to work in your underwear? Well, it turns out there is a lattice-work of reliable technique, and tips and tricks to start thinking like a comedian. It’s not quite paint by numbers, but for example, the “rule of three” is a go-to structural element — listing three things, with the last being the best.

In the end, it’s all about execution, like the Patriots on game day. My own routine was “chalky,” in horse racing parlance — safe. Stepping on stage in a black suit with a pocket square, I was self-deprecating and tried to turn on the charm. I made light of working at a think tank concerned with urban planning: You know what they say, if there’s one thing people hate more than sprawl, it’s density.

The payoff for all of us came on performance night. After weeks of workshopping, every single one of us came out of the green room and executed, even those who had struggled. We all drew energy from the audience. There is something uniquely satisfying about getting somebody to laugh.

Many of my classmates really caught the bug, attending comedy shows or participating at open mic nights at the Middle East or other venues after class. Generally, I was more interested in getting home to some Tito’s.

But you never know. Central Square is on the way home. I’ve been developing some new material, and I may need to test it out.

Anthony Flint is a fellow at the Lincoln Institute of Land Policy in Cambridge.He can be reached at anthony.flint@gmail.com.