Rise to Fame
Years after moving to Los Angeles, he was still dodging calls from his landlord over back rent. His agent dropped him. A network executive reportedly told his manager he'd 'never be a television star.' He taught acting at his old Missouri high school in the lean years, and one of his eighth-grade students was Ellie Kemper. The Mad Men director thought he was too handsome for Don Draper. He got the part anyway, won a Golden Globe his first season, and spent the next eight years racking up Emmy nominations before finally winning on his eighth try in 2015.
In the Spotlight
After Mad Men ended, the obvious move was a string of brooding prestige dramas. Instead he went the other direction. He took a deliberate comedic pivot, landing supporting roles in Bridesmaids and Baby Driver before playing a full villain in Fargo Season 5 and joining Taylor Sheridan's Landman. Your Friends & Neighbors (Apple TV+, 2025), where he plays a hedge fund manager stealing from wealthy friends to maintain appearances, marks his first lead TV role since Mad Men. He's not coasting on Don Draper nostalgia.
Side Notes
His mother died when he was 10. His grandmother took him in, and then she died too. His father died from diabetes complications during his sophomore year of college. He's talked about drawing on those losses to play Don Draper, a character defined by abandonment and reinvention. The parallel is almost too neat. He went to rehab in 2015 for alcohol dependency, and married Anna Osceola in 2023 at Anderson Canyon in Big Sur, the same cliffside location where the Mad Men series finale was filmed. Some symmetries you don't plan.