Good Will Hunting
Without a doubt Good Will Hunting was a high achievement for all involved, especially Matt Damon as he was relatively new to the scene. I heard that Ben Affleck and Damon flipped a coin to see who would get to play the lead role, lucky day for Damon.

Rounders
I loved this movie because it is gritty and I love gambling. Edward Nortorn adds a lot to this movie as the Weasely "Worm". Some think this movie started the Texas Hold'em poker craze.

Saving Private Ryan
Steven Spielberg's epic WWII movie redefines realism of war portrayed on film. Amazing acting by Hanks and the entire cast.

The Talented Mr. Ripley
A film about a strange and confused young man. Damon shows his true talents by getting out of his comfort zone, the the cool and confident roles that he usually plays. The discomfort and awkwardness of his character comes through the screen like a strong wind.

The Bourne Identity
A first rate action movie putting Damon in the lead as a highly trained assassin who wakes up not knowing who he is or where he came from. But he does find out people are out to get him, so it's time to run...

The Departed
One of Damon's very best. With the direction of Martin Scorsese and playing alongside Leonardo DiCaprio the movie is a twisting plot that has infiltration on both sides.

Invictus
Playing the part of the captain of South Africa's rugby team, Pienaar (Damon) teams up with Nelson Mandela (played by Morgan Freeman) to help bring their country together.