Conan O'Brien

O'Brien was a writer first, and for longer than most people remember: Saturday Night Live from 1988 to 1991, then The Simpsons from 1991 to 1993. He has a Primetime Emmy for Outstanding Writing for a Variety Series from that period. Then came the desk, and three decades of it, from Late Night with Conan O'Brien in 1993 through the brief and famous Tonight Show run in 2009 to Conan on TBS until 2021. He is credited as a creator on the first and the last of those, and he has hosted the podcast Conan O'Brien Needs a Friend since 2018.

The film career is a curiosity, because for years the part he was offered was himself. He appears as Conan O'Brien in Vanilla Sky, Bewitched, Now You See Me, Clear History and Thunderstruck, and even in Sharktopus vs. Pteracuda, which is roughly where that particular idea ran out of road.

The actual acting hides in animation, where nobody expects the face. He is a preening Riddler in The Lego Batman Movie, Glaxxon 5000 in The Mitchells vs. the Machines, Clarence on Final Space, David Endocrine in the Dark Knight Returns films, and Smarty Pants in Toy Story 5. The two recent live-action exceptions are the good ones: Andy Warhol in Weird: The Al Yankovic Story, and a therapist in If I Had Legs I'd Kick You, which is the first role in years to use the deadpan rather than the celebrity.