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.