Hailing from the Midwest, Bennett was born June 10, 1981 in Rossford, OH. Although he spent part of his youth in North Carolina, the actor called Toledo his hometown. Throughout his childhood, he idolized actor/comedian Chevy Chase. He performed in his first play in middle school, and continued to act throughout high school, where he was elected student council president. Upon graduation in 1999, Bennett enrolled at Otterbein College in Columbus, OH, to study theater.

After college graduation, he moved to New York City to pursue acting full time, meeting his agent on the train along the way. Within only a month following his arrival, he landed the role of Adam 'J. R.' Chandler Jr. on the ABC soap, "All My Children" in 2001. He played the rich teen for one year - his first and only foray as a regular on series television. Soon thereafter, he started taking small guest parts on popular primetime series, including a 2002 episode of "Law & Order: Special Victims Unit" (NBC, 1999- ) and a 2003 episode of "Boston Public"(Fox, 2000-04) entitled, "Chapter Sixty-Three."

Bennett made his feature film debut in 2003 with the independent movie, "Season of Youth." For this first film, he drew critical accolades and won the Best Actor award at the 2003 Palm Beach Film Festival.

However, no amount of critical acclaim or awards on the independent circuit could prepare him for the mainstream success of "Mean Girls" - the Tina Fey-penned dark comedy about the Machiavellian hierarchy that is high school. Playing the object of Lindsay Lohan's affections, Bennett held his own opposite a bevy of onscreen cat-fighters including Rachel McAdams and Lacey Chabert.

Coming off his "Mean Girls" success, Bennett landed a small role in the 2005 feature film, "Lovewrecked," as well as returned to television with a bit part on "Smallville" that same year. Around this time, he also landed a recurring role on the hit "Veronica Mars," playing the character of Casey Grant, in the 2004 episode, "Drinking the Kool-Aid" and the 2005 episode, "A Trip to the Dentist." A personal friend of comedienne Kathy Griffin, Bennett made two notable 2005 appearances as himself on her snarky reality show, "Kathy Griffin: My Life on the D-List."

Whether on the big or small screen, Bennett continued to make an impact, becoming one of the most sought after young actors in the business. After starring in the hit Steve Martin film "Cheaper By the Dozen 2" (2005) and the straight-to-DVD comedy, "Bachelor Party Vegas" (2006), he was cast in "1/4life," a comedy-drama series from "thirtysomething" creator Ed Zwick and Marshall Herskovitz, scheduled for the fall 2006-07 television season. The show would follow the lives of several 20-something friends just out of college and struggling with their first jobs in the real world.

He appeared on season 19 of "Dancing With the Stars."

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