Inside Late Night: Brian McCann on Writing, Performing, and Warming Up for Conan O’Brien

Brian McCann spent 17 years helping build Conan O’Brien‘s beautifully weird late-night universe—as a writer, as the show’s warm-up comic, and as the guy behind some of its most memorable characters, from Preparation H Raymond and the suicidal kayaker to Pimpbot 5000 and “No Reason to Live” guy.

But his original dream was quieter: after graduating college in 1987, McCann moved to Chicago to become a cartoonist. He could draw, but the writing felt flat. Looking for a way to get sharper comedically, he wandered into a tiny, early ImprovOlympic show called Honor Finnegan Versus the Brain of the Galaxy. Del Close was directing, the cast was spinning a wild narrative out of nothing, and McCann walked out feeling like he’d been put under a spell. What was supposed to be a month-long writing boot camp turned into nearly a decade of improv that he now calls his grad school—and his religion.

On one of his first days there, another new guy showed up: Chris Farley. At first, McCann thought he was just a “fat, crazy dude” with too much energy. Then he watched him work. Farley was chaotic, but also articulate, precise, and clearly channeling the same Belushi-fueled energy that had inspired so many Chicago comics. Within a few years he’d leapfrogged Second City’s whole farm system straight to the mainstage and then on to SNL.

While Chicago improv was exploding, McCann quietly built a parallel life in standup, doing character-driven sets on Caroline’s Comedy Hour, Evening at the Improv, and at the Aspen Comedy Festival. That mix—improv chops, odd characters, and standup reps—put him on Conan O’Brien and Robert Smigel’s radar when they were building Late Night with Conan O’Brien. He didn’t get hired off his first packet (or his second), but kept faxing in unsolicited ideas. Eventually, right before Thanksgiving 1996, the call came. He moved to New York the next day.

At Late Night, McCann became both a writer-performer and the face the audience saw first, taking over warm-up from Mike Sweeney. He loved the nights when he could turn a stiff tourist crowd into believers—and almost loved it more when a bit went sideways, like the time an entire studio booed him as “the I Am Not Annoying Guy” furiously banging water jugs.

The show also sent him to some very strange places, including Budapest, where he escorted a choir of ventriloquist dummies to appear on a local talk show—while their “parents” fumed that McCann was in first class and they were back in coach with their beloved puppets.

This week on LateNighter’s Inside Late Night podcast, Brian McCann joins Mark Malkoff to talk Chicago improv, Chris Farley, the long road to 30 Rock, the joy and terror of bombing in front of millions, and why Conan still feels like home.

Click the embed at the top of this post to watch now, or find Inside Late Night on Apple Podcasts, Spotify, YouTube, or wherever you listen to podcasts.