Connolly was born on Long Island, New York, the son of Eileen J. (née McMahon) and John Connolly. He is of Irish descent.
Connolly began his career at age six, appearing in television commercials including the popular "Betcha bite a chip" campaign for Chips Ahoy. In 1990, he landed his first film role, as Chickie, in Rocky V. Two years later, Connolly was cast as Shaun Kelly in the film adaptation of Myron Levoy's novel Alan & Naomi, and co-starred in the short-lived Fox sitcom Great Scott!. His appearance in the show later earned him a Young Artist Award nomination for Best Young Actor Co-starring in a Television Series. He portrayed Dabney Coleman's son in the 1993 film The Beverly Hillbillies. Connolly continued guest starring in television shows including Wings, Getting By and the medical drama ER.
From 1995–96, Connolly starred in Don's Plum alongside friends and future collaborators Tobey Maguire and Leonardo DiCaprio. Later that year, he landed the role of Ryan Malloy on the sitcom Unhappily Ever After. The show also marked Connolly's directorial debut when he directed six episodes in its fourth season. In 2007, Connolly made his full length movie directorial debut with the film Gardener of Eden, which premiered in April 2007 at the Tribeca Film Festival.
In addition to television work, Connolly has starred in several major motion pictures including Antwone Fisher, John Q, and The Notebook. In August 2007, he signed on to play a supporting character in He's Just Not That Into You, which was released in 2009. Connolly has reportedly been cast as jazz musician Benny Goodman in an upcoming movie. The film, set in the 1930s, will focus on one of the first interracial bands of the era; Nick Cannon, Brandon Routh, and rapper Ludacris will co-star.
In October 2008, Connolly was hired to direct his first music video for multi-platinum rap artist The Game, featuring R&B artist Ne-Yo. The video is for the song "Camera Phone" off The Game's album LAX.
Connolly attended the 2010 NHL Entry Draft in Los Angeles and announced the final pick of the first round for the New York Islanders.
Is of Irish ancestry.
Ex-boyfriend of Julianne Hough.
Had actually retired from acting when the creators of "Entourage" first approached him about doing the show. It wasn't until he was informed the part of Eric had been written specifically for him that he decided to take part.
His mother died in March 2009 aged 62.
Was crowned Homecoming King at his high school in 1991.
Was voted "Most Likely to be Famous" by his high school class.
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