Gary Gulman Breaks Down His Legendary Conan Stand-Up Set

Stand-up comedy segments are such a staple of late-night talk shows, but every once in a while someone comes along and does something that changes people's perceptions of what you can do in that time. That's what Gary Gulman (HBO's The Great Depresh) did back in 2016 with a much-beloved Conan appearance that fans and fellow comedians still talk about to this day.

In this edition of The Set-Up, Gulman sits down with J.P. Buck, the comedy booker for Conan, to talk about how he came up with the idea to do an entire six-minute set on the seemingly mundane premise of "the men and one woman who abbreviated all 50 states down to two letters" and how that set affected his career.

"That premise was in my notebook, and I had tried it two years into comedy, or less," Gulman said. "I used to call it Old Ironsides, because there's this ship in Boston that once a year, they take it out into the harbor to work the barnacles off, and it's from like the Civil War or the War of 1812. I'd truck it out every year, make sure it didn't work, and then put it back into my warehouse. I knew I wanted to hold onto it, because nobody else had that joke."

Buck referred to the set as being "like a great song, which is really hard to do with stand-up, to make people want to listen to it again even when they know what's coming."

"It's not hyperbole to say that that appearance changed my career significantly," Gulman said. "It got some notice when it first ran, and then sometime between nine months and a year later, Patton Oswalt shared it on Facebook and that made it go viral, I think, and that was what made it so I noticed more people at my shows, and once you have your own audience, you're able to do more jokes like that."

Oswalt called it one of those rare "perfectly written, realized, and executed comedy routines," and he praised just how ballsy it was for Gulman to use his national TV time for one long-form joke. "Do you realize how terrifying that is to risk? As a comedian? If you start down this road and it's not clicking? There's no ripcord. No bolt-hole to safety. You've chosen this track and you better hope it brings you to the next station instead of suddenly ending in warped rails over a crevasse."

With that in mind, it's understandable that Gulman was nervous about Conan O'Brien's response. "He always says something very nice, but because I'm incredibly insecure, I always compare it to things he said to other people on the show. I've heard him say things really nice about sets that I was like 'that really wasn't that good'... he said it reminded him of Bob Newhart, and I had to pinch myself, because that man was my north star."

Here's the original set in its entirety.

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Andy Hunsaker has a head full of sitcom gags and nerd-genre lore, and can be followed @AndyHunsaker if you're into that sort of thing.