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).