Jacobson was born in Chicago, Illinois, the son of Lynn Straus and news anchor Walter Jacobson. His family is Jewish and coming from Russia, Ukraine and, maybe, Lithuania. He is a 1987 graduate of Brown University. Jacobson also graduated from the Juilliard School, where he was a member of the drama division's Group 20 (1987–1991).
Jacobson and Lisa Edelstein, his Future co-star on House, appeared as a couple eating at a restaurant in the 1997 film As Good as It Gets. He played a recurring role on Law & Order as Randy Dworkin, a jovial crusading defense attorney. In 2005, he played Jimmy in the Academy Award-nominated film Good Night, and Good Luck. He has appeared in Scrubs, CSI: Miami, The Lost Room, The Starter Wife, Transformers, and The Midnight Meat Train.
Jacobson joined the cast of House as Dr. Chris Taub, a plastic surgeon hoping to secure a place on Dr. Gregory House's diagnostics team. In October 2007, he was confirmed as a regular on the show. He made a guest appearance as Alan on an episode of the USA Network's Royal Pains.
