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His film career began in the late 1980s and he has since appeared in a variety of films, television series and stage productions. He became known for his bright and layered roles, where he managed to explore various aspects of human nature.

Some of Stephen Tobolowsky's more notable works include:

1. Strawberry Rain (1989) is a drama about the life of an aging actress.

2. Big (1988) is a comedy about a boy who becomes an adult.

3. "Natural Born Killers" (1994) is a country travel thriller by car.

His talent and dedication to the profession enabled him to successfully work in the entertainment industry for decades. The extent of his contribution to cinema and television can hardly be overstated, and his work remains an important part of cultural heritage.