Mystic Pizza (1988)
School Ties (1992)
Damon took a few small roles over the next few years, but School Ties not only gave him a little more space to actually act, it also gave him a chance to work with his childhood friend Ben Affleck (Brendan Fraser and Chris O'Donnell also appeared in this 50s-set movie).
Fraser plays a Jewish kid who faces prejudiced treatment when he moves to a new prep school on a football scholarship, particularly when he butts heads with Damon, a rival for his spot on the field.
Brainiac Damon? No, on top of his ignorance, he's also flunking history.
Courage Under Fire (1996)
Fairly early in his career, Damon scored a great deal of attention in this military drama. In terms of scale, it was his biggest film yet, and he made the most of it with a committed performance.
In a supporting role, as a soldier key to the investigations regarding potential Medal of Honour recipient Captain Walden (Meg Ryan), Damon dropped a considerable amount of weight to give his drug addict a convincingly gaunt physicality.
Brainiac Damon? Yeah, this ain't your average screen junkie.
The Rainmaker (1997)
Francis Ford Coppola was impressed by Damon's turn in Courage Under Fire and cast him as the lead in this John Grisham adaptation.
While The Rainmaker is nowhere near Coppola's finest work, it's still satisfying as a mostly-straightforward genre piece, in which Damon's young lawyer, desperate for cash after graduating, takes on a seemingly unwinnable case against an insurance giant.
Brainiac Damon? You don't pass the bar exam if you're short on grey matter.
Good Will Hunting (1997)
Dissatisfied with the type of roles that were on the market, Damon and Ben Affleck got together to write this screenplay, which saw them take home an Oscar.
Both starred in the film, but Damon took the lead as a streetwise janitor who's never too far away from trouble, but just happens to be a maths genius. Not only did the pair manage to craft compelling characters, but they also capture a vivid, believable Boston neighbourhood.
Brainiac Damon? The Oscar-winning writer seems at home playing a supersmart, but modest, guy.
Saving Private Ryan (1998)
Still in the developing stages of his career, Damon was getting noticed by big-name directors, and they don't come much bigger than Steven Spielberg, who cast the young actor in a pivotal role in his WWII epic.
Despite playing the title character, Damon doesn't appear until the second half of the movie, but even with limited screentime, he keeps his performance subtle as the rescuee who's not sure he deserves it.
Brainiac Damon? It's another thoughtful character for Damon.
Rounders (1998)
While this movie received scornful reviews when it was released, it has developed a bit of a following in the meantime, for both its portrayal of poker, and also the fact it contains early performances from Damon and Ed Norton, and features John Malkovich at his most hammy.
Damon is a law student with a knack for card games, and Norton's his fresh-out-of-chokey best mate who can't help getting them into trouble. Your interest in the game will have a big impact on your ultimate enjoyment of Rounders .
Brainiac Damon? He could probably take on Rain Man at cards.
Dogma (1999)
He teamed up with buddy Affleck again, this time for Kevin Smith (who directed Ben, and Matt in a cameo, in Chasing Amy ).
The pair play fallen angels looking to get back into heaven by means of a spiritual loophole. There are plenty of interesting ideas bouncing around here, but ultimately it's a bit too cluttered and haphazard to work as a comedy, a satire, or even an adventure.
Brainiac Damon? He hasn't read the good book as closely as he should have done.
The Talented Mr Ripley (1999)
Damon subverted his Mr Nice Guy image to play it thoroughly sinister, in the most successful movie to spring from Patricia Highsmith's book series.
Anthony Minghella's thriller favours slow-burn tension over action and pyrotechnics, and as well as a superb performance from Damon, the movie is littered with spot-on supporting turns, notably Jude Law, Philip Seymour Hoffman and Cate Blanchett.
Brainiac Damon? He's a chillingly crafty one here.
Titan A.E. (2000)
This animated sci-fi movie was a notable attempt to do something a little different within the medium, but it suffered from an uneven blend of styles, and it somehow felt dated as soon as it was released.
The last film feature film directed by Don Bluth (depending on your childhood allegiance he's either an underdog hero or a poor man's Walt), it at least had a plot (a bunch of survivors travel the galaxy after Earth is destroyed) that distinguished itself from other kiddie fare.
Brainiac Damon? Not particularly, by Damon's standards.
