1. "D*ck in a Box" (12/16/06)
"D*ck in a Box" isn't just one of Justin Timberlake's best skits—it's also one of the best skits in the history of the show. The unbelievably catchy song was the first of three SNL digital shorts starring the singer and Andy Samberg. An ode to corny R&B ballads from the '90s, the bawdy tune will undoubtedly be etched in pop culture history.
Fun Fact: The song won a Creative Arts Emmy for Outstanding Original Music and Lyrics.
What's your favorite SNL skit starring JT?