Leary grew up in Dallas and first appeared on stage at thirteen. From 1993-1995 he was a founding member of an improvisational comedy troupe called Freudian Slip.
In December 1995 he and his wife moved to Chicago, where Leary studied at Second City and Improv Olympics. They now live in Los Angeles.
From 1998-2001 he co-starred as Kevin, on Telemundo's Los Beltrán. In 2000 he played Mark in the Parallax Theater Company's production of Robert Coover's The Babysitter at McCadden Place Theater in Hollywood.