In 2005, Hatosy performed opposite Al Pacino in Lyle Kessler's "Orphans", at the Greenway Court Theatre in Los Angeles. Hatosy also took on the title role in the La Jolla Playhouse production of "The Collected Works of Billy the Kid". Off-Broadway, he starred opposite Anna Paquin in the Paul Weitz comedy "Roulette". He also performed in "Roulette", an Ensemble Studio Theater production directed by Trip Cullman, whose characters include a dizzy, distant dad (Larry Bryggman), a sweet, adulterous, alcoholic mom (Leslie Lyles), a steroid-hyped son (Shawn Hatosy), and a wise-cracking, substance-abusing teenage daughter (the Oscar-winning actress Anna Paquin).