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Tobolowsky was born on May 30, 1951, in Dallas, Texas. He studied geology at Southern Methodist University but switched to theater after being cast in a production of "The Crucible." He later attended the University of Illinois at Urbana-Champaign, where he graduated with a degree in drama.

Tobolowsky began his acting career in the early 1980s, appearing in films such as The Philadelphia Experiment (1984), Nobody's Fool (1986), and Spaceballs (1987). He also had a recurring role on the television series Seinfeld (1989-1998).

Tobolowsky's breakthrough role came in 1993, when he played Ned Ryerson in the comedy Groundhog Day. His performance in the film was critically acclaimed, and he has since become one of the most recognizable character actors in Hollywood.

Tobolowsky has continued to work steadily in film and television over the years. He has appeared in numerous other films, including Memento (2000), Mulholland Drive (2001), and The Informant! (2009). He has also had recurring roles on the television series Deadwood (2004-2006), Heroes (2006-2007), Californication (2007-2014), and Silicon Valley (2014-2019).

In addition to his acting career, Tobolowsky is also a writer and a podcaster. He has written two books, The Dangerous Animals Club (2002) and The Tobolowsky Files (2017). He also hosts the podcast The Tobolowsky Files, in which he tells stories about his life and career.