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Born in Long Island, 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 movie The Beverly Hillbillies. Connolly continued guest starring in television shows like Wings, Getting By and the medical drama ER.

From 1995 to 1996, Connolly filmed 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 of 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 lead role in Drew Barrymore's new comedy He's Just Not that Into You. Most recently, 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.

Connolly was linked with his Unhappily Ever After co-star Nikki Cox. He also dated heiress and designer Nicky Hilton from January 2005 to October 2006.

In 2007, he was romantically linked with actress Haylie Duff[7]and Dancing with the Stars dancer, Julianne Hough.

In June 2007, Connolly was named one of People magazine's hottest bachelors of 2007 along with cast mate Adrian Grenier.

Connolly is a die-hard New York Islanders fan. He showed his support for the team by wearing an Islanders hat in the Entourage episode "Welcome to the Jungle".