His first movie role was in The Rules of Attraction, playing a speed freak named Quinlivan in a scene that ended up cut from the film. He played Scarlett Johansson’s character’s husband in the flashback scenes for The Island, and a cook in Waiting…. Stone was cast in Christopher Guest’s For Your Consideration as a trashy radio morning show host after Guest saw the “Cancun Coma” episode of Con. In July 2007, Stone was cast in the comedy House Broken, as Danny DeVito’s son.

Stone sold a pilot called Skyler’s Revolution to Fox Broadcasting Company and Warner Bros. Television in 2007, wherein he made prank calls to celebrities, but it was not picked up for a series. He appeared in the CSI: NY episode “Youngblood.” Stone was a contestant on Dog Eat Dog and Whammy! The All-New Press Your Luck twice (the second time in the Tournament of Losers). In 2010 he appeared in the CBS sitcom Rules of Engagement.

Stone is a regular at the Laugh Factory, The Improv, and The Comedy Store, in Hollywood, California. He made his first national stand-up appearance on The Late Late Show with Craig Ferguson on January 3, 2007. He resides in Sherman Oaks, California.

In 2013, he provided the voice for Scowler, a Pachyrhinosaurus in BBC Earth’s Walking With Dinosaurs: The Movie.