Played: Steven Black in season 1's "The Source Awards"

Particularly in the series' early days, when Tracy could still have the occasional human moment, "30 Rock" did some brilliant, biting stuff about race relations and the clumsiness of white liberals in dealing with minorities. In "The Source Awards," the show brought in Brady — who, famously, was described on "Chappelle's Show" as someone whom white people love "because he makes Bryant Gumbel look like Malcolm X" — to play Tracy's business manager and Jack's latest attempt to fix up Liz. Steven turns out to be an unappealing clod who collects tote bags, but Liz is reluctant to stop dating him for fear of seeming racist. When she finally tries to break up with him, he refuses to believe that it could be for any other reason but his skin color, which prompts Liz to ask, "So what you're saying is any woman that doesn't like you is racist?" Steven, smug, replies, "No, no, no, no, no. Some women are gay." It's not as bold a piece of self-satire as the "Is Wayne Brady gonna have to choke a bitch?" appearance with Chappelle in response to the earlier gag, but it's a fearless performance in one of the show's best, most biting episodes.

- Alan Sepinwall