Tobolowsky has been quite memorable in both film comedies and dramas, first gaining notice with a humorous portrayal of French De Mille, the documentary narrator, in Jonathan Demme's "Swing Shift" (1984). A busy character man, he appeared in seven 1992 features including "Basic Instinct", as a psychiatrist who raises serious doubts about Sharon Stone; "Single White Female", as a sleazy designer who sexually harasses and cheats Bridget Fonda; and "Sneakers", as a computer flunky who gets duped by Mary McDonnell. In perhaps his most well-known role, Tobolowsky delivered a hilarious performance as Ned Ryerson, the overly-assiduous insurance salesman who bedevils Bill Murray in the comedy hit, "Groundhog Day" (1993).
Tobolowsky has appeared regularly on a number of TV series, many of them short-lived, including a turn as a car salesman in "Against the Grain" (NBC, 1993), a product tester on the ABC sitcom "Blue Skies" (ABC, 1994) and "Dweebs" (CBS, 1995). He then played the headmaster of a private school where an iconoclastic new teacher caused problems in the NBC sitcom "Mr. Rhodes" (1996-97) and co-starred in the mini-series ""Dean Koontz's Black River" (2001) and "Kingpin" (2003). As a guest player, Tobolowsky has racked up a staggering resume of stints on dozens of popular series both comedic and dramatic, including "Alice," "Knots Landing," "Falcon Crest," "Designing Women," "L.A. Law," "Seinfeld," "Picket Fences," "Chicago Hope," "Buffy the Vampire Slayer," "The Drew Carrey Show," "Mad About You," "The Practice," "That 70s Show," "King of the Hill," "Malcolm in the Middle," "CSI:Miami" and "The West Wing."
The actor continued to appear in a long list of films as well. Among the more notable were "The Insider" (1999), "Memento" (2000), "Adaptation" (2002), "Freaky Friday" (2003) and "Garfield: The Movie" (2004).