Having stretched the limits of prime-time postmodernism with his fourth-wall-shattering cult hit It's Garry Shandling's Show, Garry Shandling faced a career-shaping decision in the early '90s. He could leverage his growing popularity for a shot at late-night talk-show stardom, or he could turn the genre on its head with a scathing satire as revolutionary in its own way as David Lynch's Twin Peaks. Thankfully, he chose the latter option. Beginning in 1992, Shandling executive-produced, co-wrote, and starred in The Larry Sanders Show, a work of dark comic brilliance that reveals the hornet's nest of neuroses, tension, and hostility beneath late-night television's reassuring façade. Of course, the ironic contrast between celebrities' polished exteriors and their tortured inner lives—represented visually by Sanders' split between flat, conventional video for its talk-show segments and gritty, documentary-like film for its behind-the-scenes footage—has long been a fixture of show-business satire. But Sanders avoids the easy irony of its imitators (Arli$$ being the direst example) in favor of more sophisticated humor that exploits the comedic possibilities of tension, discomfort, and awkward silence as masterfully as the wit of Nichols and May. Sanders explores the nebulous intersection of pain, humiliation, and comedy, creating moments that are simultaneously funny, uncomfortable, and painful. Though the show is rich with sharp one-liners, the complicated relationship of its three main characters—the titular Shandling surrogate, cheerfully Machiavellian producer Rip Torn, and blustery tragicomic sidekick Jeffrey Tambor—provided both its soul and its comic thrust. All three characters are variations on time-tested show-business stereotypes, but in the able hands of Sanders' cast, they register as complicated, flawed human beings. The Larry Sanders Show's depiction of self-loathing, back-stabbing, narcissism, and insecurity run amok ventured unusually close to the heart of darkness, which may be part of the reason it's aged so well. After all, television trends may come and go, but the turmoil, ego, and politicking that go into the act of creation remain timeless.