It's not easy to be charming and snide simultaneously, but this affable comic performer has forged a career out of delivering cutting quips with a winning smile. After starting in stand-up, Spade made a handful of TV guest appearances before signing on to Saturday Night Live in 1990. Although some viewers initially confused him with chameleon cast mate Dana Carvey, Spade fared best when playing himself (or some variant thereof), particularly during his snarky "Hollywood Minute" segments, which years later would serve as a blueprint for his Comedy Central series The Showbiz Show With David Spade. During Spade's SNL tenure, he ventured onto the big screen in a string of inane comedies, including two with late cast mate Chris Farley (Black Sheep, Tommy Boy). He then landed a role on the sitcom Just Shoot Me, playing a sarcastic underling. His next big TV moment came in 2007 when he was cast as the perpetually single Russell Dunbar in the sitcom Rules of Engagement. Spade himself has never been married, but he's been romantically linked to impressive array of Hollywood women, including Kristy Swanson, Lara Flynn Boyle, Julie Bowen and Heather Locklear.