I saw this movie for the first time on a date in college. I can't remember if it was in a theater or if it had been on home video, but I do know that I had to watch it a second time before I saw the whole thing. I hadn't expected to enjoy this movie, because even before Team America ruined Matt Damon for me, I wasn't that big of a fan. There are a couple of exceptions, like Dogma, but I can't think of an example of his work where I was just completely blown away, or even completely entertained. Good Will Hunting blew me away once I was able to watch it uninterrupted, and even now I still love the movie, even though it's been spoofed a billion times on shows like Family Guy and Robot Chicken, and even though I've watched it about fifty ba-zillion times. Do I love it as much now as the first time I saw it without distraction? No, but I always enjoy my time spent with Matt Damon, Robin Williams, and Minnie Driver.
I think that if it wasn't for the power trio in this movie, that the story would be a little boring. I like underdogs, and it doesn't get much more under than Will Hunting, the kid from Southy with the smarts to solve all the world's problems. I love the way the movie ends, because it seems to answer all the questions I might have as to how serious Will Hunting is in the pursuit of an actual education rather than scamming one through his local library. I have an old acquaintance who used to like to make a claim on education because he sat in on the occasional class at his local college, but there's a difference between listening (or reading) to someone else's work and using that work as a springboard for your own thoughts. I can rattle off facts all day, but education has allowed me to apply those facts elsewhere, and to cause and effect them into other things. Hunting had some of that same problem, confusing reading for smarts. He was smart enough to use facts to embarrass people who belittled him for his social station, but I'm not sure he didn't understand the difference between what he acquired for free and what Harvard students were paying for.
I even like the romance between Minnie Driver and Matt Damon, although to this day I don't understand the attraction for Driver's character except the physical. They acted like there was some sort of deeper bond between the two of them, and I must repeatedly miss the scene that actually shows that. They don't seem to have much in common, and there are reasons for that, but it would have been nice to see them address those differences on camera, rather than in a cut scene or two.
You can see this movie for a number of reasons. You like Robin Williams, or Matt Damon, or Minnie Driver. I think all three are involved in their better performances. You like dramas or touching underdog stories, because both of those apply as well. Whatever your reasoning, you should see this if you haven't already.