The Celebrity: Charlie Murphy as Ed Wuncler III and Samuel L. Jackson as Gin Rummy
The Appearance: “Let’s Nab Oprah” (Season 1, Episode 11)
The Reason It Worked: Because they manage to play two white Iraq War vets—and still make it funny. Murphy actually appeared in the first episode of the series, but this clip demonstrates just how crazy these two can get when they get together. Pause.
The Celebrity: Lil Wayne as teenager from New Orleans
The Appearance: “Invasion of the Katrinians” (Season 2, Episode 24)
The Reason It Worked: Because Lil Wayne got the joke. Despite the fact that the episode touched on a very touchy subject (Hurricane Katrina victims finding shelter in other cities and disrupting other families), Weezy F. did his best to bring the New Orleans authenticity straight to the Freeman family’s front door.