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Hollywood legend Jackie Cooper passed away Tuesday at the age of 88. Jackie’s career spanned over 60 years, starting off big as one of the best-known child stars of his generation.

Jackie died Tuesday at a convalescent home in Santa Monica, Calif.

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“He just kinda died of old age,” his attorney Roger Licht told Reuters, via The Hollywood Reporter. “He wore out.”

He got his start in films at a very young age, and at nine years old was nominated for an Oscar for his role in Skippy (1931) — a film based on the popular comic strip.

Jackie set and still holds the record for youngest actor ever to be nominated for a Best Actor Oscar at age nine.

At 14, he dated Judy Garland, THR reports and at 17, he had a six-month fling with Joan Crawford.

Later in his career, he starred as Perry White in the four Christopher Reeve Superman films and has also worked as a director and TV executive.

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He married Barbara Kraus, and the couple had three children. He is survived by two of his children.

Watch Jackie as a child star in 1931’s The Champ.

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