Trousdale was raised in La Crescenta, north of Glendale, California. He had planned to be an architect, but had failed at math. Instead, he had decided to study animation at CalArts, where he studied for three years. After his studying, he applied to work as an animator for Carter/Mendez Productions. He was hired in 1982 to design storyboards and do other animation. He then went to work designing restaurant menus and T-shirts.
Trousdale was hired by Walt Disney Productions in 1984 as an inbetween effects animator on The Black Cauldron (1985). Trousdale then worked as a storyboard artist on Oliver & Company (1988) and The Little Mermaid (1989). It was on the former film Trousdale became re-acquainted with Kirk Wise, his future collaborator. Wise recalled, "Gary and I actually met at CalArts in my first year, that would've been 1981 ...We didn't cross paths again until I was at Disney. I worked at the end of The Great Mouse Detective, I got laid off for a year and came back in '87/'88 on Oliver & Company in the story department and that's where Gary and I started working together."
While working on The Rescuers Down Under (1990), Trousdale and Wise were fired from the project due to creative differences, most particularly after their desire to have an Aboriginal Australian child actor hired to voice Cody was ignored. They both moved to Orlando, Florida to the Disney-MGM Studios where they developed a Roger Rabbit short film titled Buggy Buggy Blunder, which told of Baby Herman's stroller getting away from Roger while they were out in the city. Their pitch was rejected by the studio's management. Trousdale and Wise then directed the animated opening sequence for Cranium Command, an attraction ride at the Walt Disney World Resort's EPCOT Center. Trousdale explained, "...there was a shakeup on the directorial side... they said you guys go, that's how we got put together."

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