Bradford's cousins are Jonathan Svec (a member of the bands Splender and Edison) and Sarah Messer, a writer and poet.

He was Homecoming King, captain of the tennis team, and was voted "best looking" and "favorite actor" by his high school class (although he was not in the drama club).

As a child actor, Bradford starred in the well-reviewed films Prancer (1989), Presumed Innocent (1990), King of the Hill (1993), and Far from Home: The Adventures of Yellow Dog (1995).

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.

In 2009, Bradford was cast as one of the leads in I Hope They Serve Beer in Hell, based on Tucker Max's bestselling book.