Arenberg attended Santa Monica High School with future "brat packer" actors Sean Penn, Robert Downey Jr. and Emilio Estevez, and co-wrote a play with Estevez which was directed by Penn. Lee's first professional job was in 1986 at the Mark Taper Forum in "Ghetto", a play directed by Gordon Davidson. Within weeks he was cast in three films, including the role of Norton in the feature Tapeheads (1988) opposite the film's co-stars Tim Robbins and John Cusack. Guest appearances on television began in 1987 with the hit sitcom Perfect Strangers (1986), and have continued with memorable roles such as the parking space-stealing New Yorker on Seinfeld (1989) and as the murderous rock promoter opposite Katey Sagal and Sam Kinison in Tales from the Crypt (1989), as well as roles on Arli$$ (1996), and Friends (1994). Arenberg can also be seen in the role of the notoriously huge studio head, Bobby G., on the controversial syndicated comedy film Action (1999) opposite series star Jay Mohr.