Young Matt Damon: A Look Into the Actor's Early Acting Career

He only had 12 credits to complete in order to bring home his Bachelor of Arts in English diploma from Harvard University. Instead, Matt Damon dropped out, sought acting projects, eventually moved to Hollywood to pursue his craft as a young actor and brought home a coveted Oscar for Best Original Screenplay for Good Will Hunting (1997), which was originally written as an early treatment of the screenplay for an English class at Harvard. Some would consider this a fortuitous trade-off.

The actor's Massachusetts origin story

Born Matthew Paige Damon on August 19, 1969 in Boston, Massachusetts, when he and best friend and fellow thespian Ben Affleck were children, they lived two blocks away from each other. The two bonded over many things, one being that they were avid collectors of Daredevil comics.

The pair met when they were 10 and 8 years old, Damon being the older of the two. Beyond Daredevil, they became fast friends after they discovered a mutual love for baseball and movies. Their friendship was cemented when Affleck defended Damon in a fight at school.

Bit by the acting bug

Damon's love of acting began at an early age. He performed in several high school theater productions and credited his drama teacher as being an important artistic influence.

While at Harvard as an English major, Damon kept skipping classes to pursue acting projects such as  Burn This and A … My Name is Alice. He also appeared in the TNT original film Rising Son (1990), and had a role in the ensemble cast in the prep school drama, School Ties (1992).

It was during the 90s that he and Affleck wrote Good Will Hunting about a young math genius — it was the film that changed everything for both of them.

This time around, outside of the confines of Harvard, Damon got advice from some of Hollywood’s best: director Rob Reiner, screenwriter William Goldman and writer/director Kevin Smith. When he moved to Los Angeles and bunked down in Affleck’s apartment, the two began working on the script more seriously.

Armed with a $20,000 paycheck for his role in 1995’s TV western The Good Ole Boys, the money kept Damon and roomie Affleck free from having to take other jobs so that they could focus on writing the script.

“The role was so close to my heart because my best friend and I invented him, he’s from Boston and it was what we knew," he told Entertainment Weekly in 2007. "The stakes were pretty high with Good Will Hunting and it worked out as best as it can in this business — people saw the movie, it got good reviews, I was happy with the finished product and they gave us an Oscar.”

Here’s a look at some early roles in Matt Damon’s illustrious Hollywood career during his time as a young actor.

Matt Damon movies as a young actor

Mystic Pizza (1988)

After arriving in Hollywood, Damon managed to get his first break with a small part in this romantic comedy starring Julia Roberts. If you blinked, you might have missed his brief appearance as Steamer. The film did not do what he had expected and his film career failed to take off.

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School Ties (1992)

Not one to let failure discourage his ambitions, Damon went for an audition and managed to get a starring role as Charlie Dillon, the rival to Brendan Fraser’s David, in this ensemble movie, while bestie Affleck had a supporting one.

Glory Daze (1995)

By this time, he had made somewhat of a name for himself in Hollywood, but not a big enough one to capture casting agents’ attention for this buddy film.

Damon had a non-speaking role as former El Rancho housemate Edgar Pudwhacker, while his pal Affleck had a starring role.

Courage Under Fire (1996)

To look the part of a Gulf War vet addicted to opioids, Damon dropped 47 pounds for the role within a 100 day period on a self-prescribed diet and fitness regimen. His authenticity in the role as Specialist Andrew Ilario garnered him critical notice.

Good Will Hunting (1997)

This film was nominated for nine Academy Awards, one of which, as noted, when to Damon and Affleck for Best Original Screenplay. Will Hunting is a janitor at MIT with a gift for mathematics, and this wayward young man needs help from a psychologist, played by Robin Williams, to find his own identity and direction in life.

The movie, also starring Minnie Driver as Skylar and Affleck as Chuckie, immediately thrust the pair into the Hollywood limelight. Damon had been working as an actor for 11 years and found the "overnight" success nearly indescribable.

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The Rainmaker (1997) Matt Damon young

Francis Ford Coppola cast Damon as Rudy Baylor in his legal drama after seeing his performance in Courage Under Fire. By the time filming began, Damon had regained most of the 47 pounds he had previously lost.

Based on a John Grisham novel of the same name, Matt had star billing alongside Claire Danes, Jon Voight, Danny DeVito and other notable actors. As the story goes, Rudy had no high paying jobs lined up after law school graduation, so he serves drinks at a Memphis bar to make ends meet. Rudy eventually begins meeting and associating with unsavory characters and finds himself involved his first courtroom drama.

To perfect his Southern accent for his role as Baylor, Damon actually tended bar in Knoxville, Tennessee for free. He later hired one of the customers to serve as his dialect coach.

Saving Private Ryan (1998) Matt Damon young

Damon plays the title role in Steven Spielberg's acclaimed World War II film. As Private James Ryan, who is brought to safety and discharged as a result of his three brothers all dying in the war, Ryan delivers a very unfunny and unimpressive story of the last night he spent with his siblings.

The horrible speech was a lousy ad-libbed delivery that made Damon’s character ring true as an oddball, uninformed, immature kid who was fated to be at the center of this rescue mission.

Rounders (1998) Matt Damon young

The actor stars as earnest New York City law student Mike McDermott, whose one big gift is poker. He dreams of winning the World Series of Poker, but loses his entire bankroll in a single hand to a Russian mobster.

McDermott eventually becomes a reformed poker player who finds that he must return to playing big stakes poker in order to help a friend pay off loan sharks.

Dogma (1999) Matt Damon young

Damon rejoins his BFF Ben Affleck and comedian Chris Rock in this comedy, deemed blasphemous by religious groups.  He plays one of two fallen angels in this fantasy comedy, both rejected from paradise and now headed to none other than New Jersey — where they find a loophole that can get them back into heaven. The only downside to this plan is that it will destroy humanity.

The Talented Mr. Ripley (1999) Matt Damon young

Damon is antihero Tom Ripley, a working class young man who tastes the good life and will do anything to live it. Once again, Damon went on a diet and fitness regimen to lose 25 pounds and convincingly conveys his character’s slide from innocent eagerness into cold determination.

The film received so-so reviews, but his performance was praised and singled out, even though the movie boasted big stars like Gwyneth Paltrow, Cate Blanchett and Jude Law. Always giving authenticity to his role, Damon learned how to play piano for the film.

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