Jon Glaser has built one of the most delightfully odd comedy résumés around—since first rising to prominence as a writer for Late Night with Conan O’Brien, he’s created the series Delocated and Jon Glaser Loves Gear, popped up on Parks and Recreation, Girls, and Curb Your Enthusiasm, and even produced Jason Kelce’s ESPN variety/talk show.
But long before that, he was a Second City alum who didn’t even think of himself as a writer. In 1995, Saturday Night Live flew him to New York to audition, and he went bold, impersonating King Hussein of Jordan raving about bubble baths. SNL passed, but Robert Smigel saw the tape and hired him to write on The Dana Carvey Show instead.
At Carvey, Glaser’s “world leaders in their baths” sketch made it to air (with Smigel playing King Hussein), and he learned that sometimes the right break isn’t the one you expected.
Conan was the perfect fit. Hired in April 1998, Glaser quickly started getting pieces on: the Witness Protection impressionist (every impression sounded equally distorted), “Jeremy and Ira” with Brian Stack, and the “Celebrity Secrets” runner.
Five years in, he left—tearfully—to chase performing again. “The gap had narrowed” between what thrilled him and what didn’t. Still, he calls Conan a dream job: supportive room, thick skins, and daily chances to try something odd.
This week on LateNighter’s Inside Late Night podcast, Jon Glaser joins Mark Malkoff for a deeply funny, surprisingly tender look back at his years with Conan O’Brien—what he learned, what he risked, and why absurdity still feels like home. As Glaser puts it: “The stuff that made me laugh the hardest was always the stuff that made no sense. If it’s making us laugh, that’s the only rule that matters.”
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.
