Benjamin was born and raised in Texas. He studied foreign affairs and economics at the University of Virginia, and after graduating, moved to New York to pursue his passion for acting.
Whilst in New York, Benjamin appeared in the off-Broadway show Life is a Dream at the Soho Repertory Theatre.
He also performed in numerous productions at the Williamstown Theatre Festival and at the University of Virginia, including Measure for Measure and Zoo Story before moving to Los Angeles and winning the leading role in The OC.