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

Some of Stephen Tobolowski's more famous works include:

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

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

3. "Natural Killers" (1994) is a thriller about traveling around the country by car.

His talent and dedication to the profession enabled him to work successfully in the entertainment industry for decades. The extent of his contribution to film and television is hard to overstate, and his work remains an important part of cultural heritage.