Born March 5, 1974 in Long Island, NY, Connolly started his acting career at age 6, appearing in numerous commercials including the “Betcha bite a chip” campaign for Chips Ahoy. He made his acting debut in 1990’s “Rocky V,” playing Chickie. In 1993, he played Dabney Coleman’s son in the feature film adaptation of TV’s 1960s camp series, “The Beverly Hillbillies.” 1995 was a good year for Connolly. Not only did he co-star with friends and future collaborators, Tobey Maguire and Leonardo DiCaprio in the film “Don’s Plum,” he landed his first major role in a television series. Connolly played Ryan Malloy on the WB series, “Unhappily Ever After” (1995-99). During the show’s fourth season, Connolly was given the rare chance to pursue his other passion – directing six episodes of his own show. After appearing in “John Q” (2002), Connolly made two more important friends. His relationship with “John Q” director Nick Cassavetes became one of mentor/tutor and would bode well for Connolly’s directorial aspirations in the future. As an actor, Connolly had another admirer in “John Q” star Denzel Washington. When Washington made his directorial debut with “Antone Fisher” (2002), he cast Connolly to play the role of Slim.

Although Connolly had made some high-placed buddies who admired his ambitions, he had yet to land that one defining acting role that would make him a household name. All of that changed in 2004, when the young actor landed the part of Eric Murphy in the Mark Whalberg-produced series “Entourage.” The smart HBO show premiered to instant acclaim in June. The unflinching look at the rise of movie star Vincent Chase and his attached-at-the-hip posse of good buddies became an instant hit on the cable network – a sort of Hollywood-based “Sex in the City” for men. As Eric, Connolly was able to show both his dramatic and comedic skills to equal effect, always trying to steer the girl-crazy and career-lazy Chase (Adrien Grenier) on the right path. Connolly showed particular energy during his verbal head butting sessions with Chase’s obnoxious agent Ari Gold (Jeremy Piven), a comedic highpoint of every episode.

Off screen, Connolly generated more tabloid buzz than any of his co-stars, due to his on-and-off relationship with heiress/designer/celebutante Nicky Hilton (the slightly less-reported-on sister of Paris). But there was more to Connolly than his onscreen gig and headline-making girlfriend. Connolly made his directorial film debut with the 2003 short "Whatever We Do," starring Robert Downey Jr., Tim Roth, Amanda Peet and Zooey Deschanel. The short, which was produced by old friends Tobey Maguire and written by Nick Cassavetes, premiered at the Sundance Film Festival in 2005. In 2004, Cassavetes again cast the youthful-looking actor in his three-hankie weeper, “The Notebook.” The film proved a surprising hit in the middle of an action-packed summer, and Connolly garnered excellent reviews playing Ryan Goslings’ doomed friend Fin. With his success in front of the camera well assured each Sunday night on “Entourage,” Connolly again pursued his directing ambitions. In 2005 he took the helm of “Gardener of Eden," a feature film produced by Leonardo DiCaprio’s production company, Appian Way.