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.
[Photos via @sammifax and @jessebradford]