21. 'Upright Citizens Brigade' (1998-2000)
Soon after migrating to New York City from Chicago in 1996, the live-improv crew of Amy Poehler, Matt Walsh, Matt Besser and Ian Roberts found space for their hallucinatory sketch and prank show on Comedy Central. Never has a scripted show so flaunted its improvisational origins: Many sketches were developed through the form, and most episodes were structured like Del Close's signature improv form, "the Harold." In addition, concepts like "ass pennies" and "supercool" felt like vivid details plucked straight from the subconscious, retaining the insider, you-had-to-be-there quality of the troupe's live performances. "I know we've never stopped anything for going too far," Poehler told the Onion A/V Club in 2008, of the UCB's sense of play. "I guess if it continues to be funny, there's no such thing."