Growing up, Matt Damon’s brother Kyle picked up on hints that his younger brother wanted to be a star. “Matt was a big Michael Jackson fan. He would go into his room, put on a white glove, and spin around,” Kyle told Artworks. Damon went to high school at Cambridge Rindge and Latin, where he took theater classes all four years. He also participated in the school’s stage productions, sometimes with underclassman Ben Affleck. He credited the program’s excellent teacher for nurturing their budding talent, telling Harvard Magazine, “[We] just came out with a real love of theater and acting.”
When Damon landed at Harvard for college, he continued to take theater classes. His former teacher, David Wheeler, told Daily News, that he was stunned by the student’s performance in a scene from Sam Shephard’s “Fool For Love.” “It was extremely mature and powerful and a total surprise,” he said. “What was immediately clear was that he was very, very talented.”
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Yet, even with all this talent, Damon still struggled to land roles early in his career. “There are times I’ve been rejected that would spin your head around,” Damon confessed to Time. Even after landing a few parts, he still felt it was impossible to compete with other elite Hollywood actors. “I was so low on the pecking order that if Brad Pitt, Johnny Depp, and Leonardo DiCaprio and every other guy passed on a script, maybe I’d get an audition,” Damon told the Independent.
