5. Derek Jeter, 2001
The Yankees and Saturday Night Live are New York institutions, so it made sense to have Jeter, the face of the franchise, serve as host just months after the terrorist attacks of September 11. And Jeter definitely embraced the role, dressing in drag – alongside David Cone and David Wells – in a sketch called "Yankee Wives," and dismissing his own heartthrob status ("Derek Jeter looks like if the Rock had sex with a Muppet.") That, combined with a hilarious opening monologue in which he smashed line drives at unsuspecting audience members, made his turn on SNL a classic.