[3] He graduated from Hunterdon Central Regional High School[2] and studied acting in New York at the American Academy of Dramatic Arts and David Mamet's Atlantic Theater Company.

[3] Osborne's first film role was a small part in School Ties (1992) with Brendan Fraser, Matt Damon, Ben Affleck, and Chris O'Donnell.

His character Emile in School Ties inspired Osborne to write the screenplay for the film Dropping Out, in which he starred alongside David Koechner, Adam Arkin, John Stamos, Katey Sagal, and Fred Willard.

For Uncle Kent, which debuted at the 2011 Sundance Film Festival, Osborne served as co-writer and co-producer, as well as playing the title role, loosely based on his own life.

Osborne also worked as a voice director for The Marvelous Misadventures of Flapjack, Bee and PuppyCat, Adventure Time and Steven Universe and a story consultant for Cartoon Network Development Studio Europe's very first show ever created The Amazing World of Gumball.