Rise to Fame
The pie scene in American Pie (1999) was the kind of career moment that locks you into a lane forever. He'd already done respectable work, earning a Daytime Emmy nomination on As the World Turns and making his Broadway debut at 12. None of that mattered once the movie grossed $235 million worldwide and turned him into the guy from that scene. He reprised Jim Levenstein in American Reunion in 2012. The franchise earned roughly $1 billion total. His reputation earned him something more complicated.
In the Spotlight
Orange Is the New Black was supposed to be the pivot. He joined as Larry Bloom, Piper Chapman's fiance, in 2013, won a SAG Award with the ensemble, and spent two seasons as the character audiences most actively rooted against. His exit before Season 3 was mutual. Since then, he's bounced between Netflix baking competitions, Fox sitcoms, and co-hosting a TBS revival of Dinner and a Movie with his wife. His 2025 directorial debut Getaway, a comedy thriller he also wrote, landed a global distribution deal with Republic Pictures after Zurich. Making your own material when Hollywood stops calling is a move, not a pivot.
Side Notes
At 12, he made his Broadway debut alongside Judd Hirsch. At 24, he played Benjamin Braddock opposite Kathleen Turner in The Graduate on Broadway. None of this registers in his public image because of a pastry. He turned down the Ted Mosby lead in How I Met Your Mother, a fact he confirmed in 2021, which means he passed on nine seasons of network television. He's also the guy who made sexual jokes about Ann Romney and Janna Ryan in 2012, then tweeted jokes about Malaysian Airlines 65 minutes after MH17 was shot down in 2014. He has a documented talent for generating backlash.