Part of From Stand-Up to A-List featuring Eddie Murphy and Robin Williams, Famous After 40 with Samuel L. Jackson and Christoph Waltz, and The Office with John Krasinski.
He spent close to a decade in the comedy trenches before anything stuck. Second City from 1991, where Stephen Colbert was briefly his understudy. The Dana Carvey Show lasted seven episodes. Then six years as a Daily Show correspondent doing "Even Stevphen" debates with Stephen Colbert. The actual landing came in 2005, when The Office and The 40-Year-Old Virgin hit simultaneously. He co-wrote Virgin and played the pathetic lead with enough warmth that critics expected cringe and got something genuinely funny. Michael Scott worked on the same principle: he made the embarrassing character worth rooting for.
He left The Office after season 7 and the industry wasn't sure what to do with him without Michael Scott. Then Foxcatcher happened in 2014: prosthetic nose, added weight, a real-life murder case, and an Oscar nomination that nobody saw coming. The pivot into drama wasn't a one-off. Beautiful Boy, The Big Short, Vice. He spent years taking parts that required disappearing into someone damaged. In 2024 he made his Broadway debut in Uncle Vanya at Lincoln Center. The Four Seasons limited series with Tina Fey arrived on Netflix in 2025. He's not coasting on nostalgia, which is unusual for someone who could easily get away with it.
Before comedy, he delivered mail for the USPS in Littleton, Massachusetts and quit after seven months because his boss told him he wasn't fast enough at the job. He met his wife Nancy Walls at Second City, where she was a student in a class he was teaching, and she later appeared in The Office. The Stephen Colbert connection goes back to 1991: Stephen Colbert was his understudy at Second City, they moved to New York together to join The Daily Show, and spent years doing fake debate segments as "Even Stevphen." His most consistent collaborator isn't an actress or a director. It's the improv circuit.