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Jesse Bradford

Then: We first fell in love with Jesse when we played nice guy Cliff, Torrance's (Kirsten Dunst) love interest in Bring it On. After the success of the movie, he snagged lead roles in Clockstoppers and Swimfan, and appeared on The West Wing. Bradford is also a Columbia graduate, and was an investor in Manhattan nightclub The Plumm (now closed). Now: Bradford is rumored to be dating rapper/singer/songwriter Azealia Banks. He's currently starring in the TV series Sequestered. Jesse Bradford ThenJesse Bradford Now [Photos via @sammifax and @jessebradford]
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