A busy supporting player in films since the 1980s (often playing bosses, prosecutors, principals, or just plain oddballs), Tobolowsky played minor roles in Spaceballs, Swing Shift (with Goldie Hawn), The Philadelphia Experiment, and Checking Out. He also co-wrote the screenplay for the 1986 film True Stories. Larger parts followed, including an FBI man in Thelma & Louise, psychiatrist Dr. Lamott in Basic Instinct, irritating insurance salesman Ned Ryerson in Groundhog Day, and amnesiac Sammy Jankis in Memento. Other film credits include Radioland Murders, Single White Female (with Bridget Fonda and Peter Friedman), Failure to Launch, My Father the Hero, and The Time Traveler's Wife.
On television, Tobolowsky was a regular on several one-season series in the '90s (including another salesman type on Against the Grain and the headmaster on Mr. Rhodes). On longer-running series, he recurred on Glee (as Sandy Ryerson), Heroes (Bob Bishop), Deadwood (Hugo Jarry), Californication (Stu Beggs), CSI: Miami (as a state attorney), and later The Goldbergs (Principal Ball). He guest starred on Alice (with Linda Lavin), 227 (with Alaina Reed), Cagney & Lacey, Seinfeld, The Drew Carey Show, the Perry Mason TV movie series, Mad About You, The West Wing, The Closer, Desperate Housewives, Boston Legal, Community, and Law & Order: Special Victims Unit.