The Brilliant Comedian (And My Idol) Gary Gulman Is Posting Viral Joke-Writing Tips That Are Ruining My Life

If you’re not familiar with Gary Gulman, I would encourage you to watch ALL of his work, immediately. He is, for my money, the best joke-writer in the business. And that’s not a hot take. If you talk about the minutiae, the surgical precision, the mathematical quantification of laugh-return-per-word, Gulman and Seinfeld are in a class of their own.

The second time I ever performed standup was at a place called the Comedy Studio in Cambridge, MA. It was February of 2011, my senior year of college. I had no job waiting after graduation and I was quietly incubating the idea of moving to New York to pursue “comedy,” whatever that meant. The Comedy Studio was a mainstay for Boston comedians, overseen by the wonderful, eccentric Rick Jenkins and perched above the odiferous Hong Kong Chinese restaurant. I was terrified, but I had (what I thought was) an automatic joke about cumming on girls’ faces (classic!).

Growing up, I only had porn as my reference for sex. I treated porn as an instructional video. Fast-forward a few years, I’m losing my virginity and I start cumming on her face. She says “What the FUCK?” I said “are we not watching the same instructional videos? Because in every one I’ve seen, this is how it ends.” 

Side-splitting, am I right? Also a joke that would go over GREAT today.

As I waited for my five-minute turn, I watched a range of comedians take the stage. It was a Wednesday night but Rick had the ability to pack the place with great crowds every night of the week. I wasn’t familiar with Gary’s work yet, but he was on the lineup two spots ahead of me. I still remember, word-for-word, a joke he told:

“I was in that Dunkin’ Donuts on the corner earlier. The sign said ‘February is chocolate lovers’ month!’ I’m pretty sure they prefer ‘Black history month.” 

That was THE lightbulb moment for me as a comedian. That joke, more than any other joke I’ve heard, made me think I want to do THAT.

Eight years and hundreds of open mics later, I’ve learned that it’s impossible. It’s impossible to write a joke as well as Gary Gulman. Every single word is intentional; each pause and inflection serve a purpose. He studies his sets the way that Peyton Manning watched tape. It’s a mastery and commitment to the art that few possess, or are willing to strive for. I find it daunting.

Here’s a bit he did on Trump long before Trump was thinking about the presidency:

And here’s the best five-minutes on Trader Joe’s you’ll ever hear:

Lately, Gary has been writing a joke tip a day. People love them. Not me. I can barely read them without breaking down in a panic attack. I force myself to read them because I know they’re the bitter medicine that will make me better, but they also shine a surgical light on my meager and pathetic effort to improve at my job. Each tip is like opening up the blueprints to a more successful career and seeing that the cost of parts, labor, contracting, and plumbing is a LOT more than I’m currently spending. And here I was, thinking that I was trying! Here I am, telling people that I do 5 sets a week and enjoying when people say, “Wow! That’s a lot.”

Here are the tips that resonated the most with me, but check out his twitter @garygulman for the full list:

Do you know how many words there are in a 10-minute set? Pages. Pages and pages. I asked Gary about this when he did Barstool Breakfast a while ago, and he said he does this every single morning. It’s part of his routine. He puts on his headphones and just transcribes words that he already knows by heart. He’ll do three sets a night and do this for each one. And I thought being a court stenographer was boring! Christ.

Hell, I’m bringing back that face-cumming joke tonight! Thanks Gary.

People sometimes email me, asking me for tips on how to improve their writing. I’m in no place to give anyone advice, but #18 applies to writers/bloggers big time. READ. Nobody reads anymore. I can tell you that reading is the single most important “workout” I do as a writer.

Hopefully, these tips provide more direction than anxiety for some of you. For me, the tips have felt like walking into our college gym, seeing the conditioning workout written on the board, and knowing immediately that I was going to puke.

But at the end of it, you’ll be better.

PS- I had Gary on Barstool Breakfast some months ago, when Willie was on his honeymoon. What Conor McGregor’s recognition meant to Robbie Fox, having Gary on my radio show meant to me. It was absolutely insane that the person who inspired me to do this was shooting the shit with me on my show. If you listened to that show, you might have laughed at my giddiness. I couldn’t help it. Pretty great.

PPS- here’s a joke I’ve worked on for a couple years. Hope you like.