This article originally ran in 2018. We’re re-running it in honor of Conan’s final episode, which airs Thursday, June 24 at 11 p.m. EST on TBS.
Today marks the 25th anniversary of the debut of Late Night With Conan O’Brien. NBC rolled the dice on the veteran Simpsons and Saturday Night Live writer, plucking him from relative obscurity to take over for no less a luminary than David Letterman. But after a famously rocky start, the series became a springboard for ’90s alt-comedy talent and turned its endlessly sardonic host into a late-night legend. To commemorate its 14-season, 2,725-episode run, here are a handful of The A.V. Club’s favorite clips, which are just as surprising, subversive, and silly today as they were when they first aired.