A product of Cambridge, Massachusetts, where he was born on October 8, 1970, Damon grew up in prosperous surroundings with his tax preparer father, college professor mother, and older brother. At the age of ten, he made the acquaintance of one Ben Affleck, a boy two years his junior who lived down the street. The two became best friends and professional collaborators. Educated at Cambridge's Rindge and Latin School, Damon was accepted at Harvard University, where he studied for three years before dropping out to pursue his acting career. During his time there, he had to write a screenplay for an English class: it went unfinished, but it would later be dusted off and turned into Good Will Hunting.

Arriving in Hollywood, Damon got his first break with a one-scene part in Mystic Pizza (1988). However, his film career failed to take off, and it was not until 1992, when he had a starring role in School Ties, that he was again visible to movie audiences. As the film was a relative failure, Damon's substantial role failed to win him notice, and he was back to laboring in obscurity. It was around this time, fed up with his Hollywood struggles, that Damon contacted Affleck, and the two finished writing the former's neglected screenplay and began trying to get it made into a film. It was eventually picked up by Miramax, with Gus Van Sant slated to direct and Robin Williams secured in a major role.

Before Good Will Hunting was released in 1997, Damon won some measure of recognition for his role as a drug-addicted soldier in Courage Under Fire; various industry observers praised his performance and his dedication to the part, for which he lost forty pounds and suffered resulting health problems. Any praise Damon may have received, however, was overshadowed the following year by the accolades he garnered for Good Will Hunting. His Oscar win and strong performance in the film virtually guaranteed industry adulation and steady employment, something that was made readily apparent the following year with lead roles in two major films. The first, John Dahl's Rounders, cast Damon as a former card shark trying to make good, despite the temptations posed by his ne'er-do-well buddy (Edward Norton). Despite a name cast and preliminary hype, however, the film proved a relative critical and financial disappointment. The same could not be said of Damon's second film that year, Steven Spielberg's Saving Private Ryan. As Ryan's title character, Damon headlined an all-star line-up and received part of the lavish praise heaped on the film and its strong ensemble cast.

The following year, Damon further increased his profile with leads in two more highly anticipated films, Anthony Minghella's The Talented Mr. Ripley and Kevin Smith's Dogma. The former cast the actor against type as the title character, a psychotic bisexual murderer, and featured him as part of an improbably blonde and photogenic cast that included Cate Blanchett, Jude Law, and Gwyneth Paltrow. Dogma also allowed Damon to go against his nice-guy persona by casting him as a fallen angel. One of the year's more controversial films, it reunited him with Affleck, as well as Smith, who had cast Damon in a bit role in his 1997 film, Chasing Amy. Taking a break from psychosis and religious satire, Damon next turned-up in notable performances in a pair of low-key dramas, The Legend of Beggar Vance and All the Pretty Horses (both 2000), beforeappearing in director Steven Soderbergh's remake of the Rat Pack classic Oceans 11 the following year.