Bradford was born Jesse Bradford Watrouse in Norwalk, Connecticut, the only child of actors Terry Porter and Curtis Watrouse, who appeared in commercials, soap operas, and industrial films.
His mother also played his character's mother in Hackers (1995). Bradford's cousins are Jonathan Svec (a member of the bands Splender and Edison) and Sarah Messer, a writer and poet.
He began acting at the age of eight months, appearing in a Q-Tip commercial. At his parents' encouragement, Bradford began modeling and auditioning for acting roles; his first film appearance was as Robert De Niro's son in Falling in Love (1984).
He graduated from Brien McMahon High School, where he was a self-described geology nerd. He was Homecoming King, captain of the tennis team, and was voted "best looking" and "favorite actor" by his high school class (although he wasn't in the drama club). He went on to attend Columbia University, from where he graduated in 2002 with a degree in film.
As a child actor, Bradford starred in the well-reviewed films Presumed Innocent (1990), King of the Hill (1993) and Far from Home: The Adventures of Yellow Dog (1995). Subsequently, he has had several notable roles in motion pictures, including Romeo + Juliet (1996) and Bring It On (2000), playing the romantic interest. In 2002, he appeared as the lead in two films — Clockstoppers and Swimfan. He also had a minor role as White House intern Ryan Pierce for nine episodes during the fifth season of The West Wing.
Bradford played the role of Rene Gagnon in the 2006 film Flags of Our Fathers, based on the book of the same name by James Bradley.
The film is about the Battle of Iwo Jima and was directed by Academy Award-winning director Clint Eastwood. Most recently, Bradford has been cast as one of the leads in I Hope They Serve Beer In Hell, based on Tucker Max's best-selling book.
He was an investor in the Manhattan nightclub The Plumm, along with Chris Noth, Samantha Ronson, and Noel Ashman, among others.
Bradford joined the main cast of the short lived NBC courtroom drama series Outlaw in 2010
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