As a teen, he popped up on both the big and small screens before landing on the moderately successful Married... with Children rip-off sitcom Unhappily Ever After. During his tenure, Connolly directed a number of episodes and went on to helm the Sundance-screened short Whatever We Do and later, the feature Gardener of Eden. But it was the Hollywood-insider dramedy Entourage that turned him into a bold-face name. Playing an up-and-coming movie star's manager and lifelong friend, Connolly flexed his dramatic and comic muscles and showcased his sex appeal, while off screen, he made headlines in the gossip pages as he romanced high-profile women such as Nicky Hilton and Haylie Duff.
- Began acting at age 6; first gig was a Chips Ahoy commercial.
- Film debut was in 1990's Rocky V.
- Old friends with Leonardo DiCaprio and Tobey Maguire; starred with the latter in 1992's short-lived Fox sitcom Great Scott!.
- His directorial debut, the 2003 short Whatever We Do, starred Robert Downey Jr., Amanda Peet and Tim Roth. It was produced by Maguire and premiered at the Sundance Film Festival.
- In 2007, directed his first full-length film, Gardener of Eden.
- Also directs music videos.
- 2008, Screen Actors Guild Awards — Outstanding Performance by an Ensemble in a Comedy Series: Nominee
- 2007, Screen Actors Guild Awards — Outstanding Performance by an Ensemble in a Comedy Series: Nominee
- 2006, Screen Actors Guild Awards — Outstanding Performance by an Ensemble in a Comedy Series: Nominee
- 2009, Golden Globe — Best Performance by an Actor in a Television Series - Musical or Comedy: Nominee
- Nicky Hilton — Ex-significant Other