#6 "The Betrayal" -- Seinfeld (1997)
Seinfeld has earned its place in the pantheon of great television because it rewrote the rules for sitcoms. Its humor is organic and daring, refusing to be confined to pre-established patterns. One early episode that best exemplifies this is "The Chinese Restaurant," noteworthy because the entire episode takes place in one location (the aforementioned restaurant) and because it involves nothing more than Jerry, George and Elaine talking while they wait for a table. More than any other, that episode earned the show its reputation as a show about nothing.
I have chosen, however, an episode from one of the later seasons that I think is both funnier and more daring. "The Betrayal" again illustrates the risk-taking mentality of Seinfeld as the entire episode is told in reverse order. We begin at the end of the episode and then the scenes work backward as the audience has to put the pieces together to form the puzzle. Punchlines land first only to be followed by the set up later on. We first encounter Kramer with his tiny lollipop, which then grows throughout the episode to its original, humongous size. It is a risky and gimmicky episode. But what makes it stand out is that the gimmick works.