Born in Boston, Massachusetts, but raised in West Orange, New Jersey, Wolf attended George Washington University and earned a degree in finance.
Wolf's entry into dramatics was facilitated by family friend and former actor Clint Brady, who thought the youth had a natural gift for acting. Wolf took his advice and studied acting at New York's HB Studio and then studied under Robert Carnegie at Playhouse West in California. He started out on television, appearing in several commercials and then graduated to bit parts and guest-starring roles on series ranging from Saved By the Bell to The Commish.
Wolf was cast as Bailey Salinger, the second-oldest of five orphaned children on Party of Five in 1994. Wolf made his feature film debut with a starring role in Double Dragon (1994). Wolf last appeared in the WB drama Everwood.