The first three are obvious but they're too good to be left off. 1. Goodfellas 2. The Godfather 1 3. The Godfather 2 4. Snatch 5. Gangs of New York (if counted, otherwise Donnie Brasco or Once Upon...America) On the subject, I have to say that The Departed and Scarface (remake) are overrated. That's not saying that they're bad movies because they're not. I like The Departed a lot but I know a lot of people who say that it is one of the best movies to come out in the past 10 years. One might think this after the first time but it just doesn't hold up on repeat viewings. I think what made it so good the first time was how unexpected the ending was. When you know what's going to happen, the suspense is lost. One might say that this is true with any movie you've already seen but I think there are a lot of movies that can still hold suspense even when you know what's coming next. I think The Departed failed to do so. It's a good movie, no doubt, but I would have to say it's overrated and probably one of the weaker Best Picture winners in a long time (Crash being the weakest, I didn't think it was anything special at all). But last year's best picture nominees were weak overall so I guess you can't fault it for that. And I don't know what the appeal is with Scarface. I guess it's just lost a lot with me because every single rapper/athlete/anyone who's ever been on Cribs owns it and talks about it. As for something not yet mentioned, I'll throw in Road to Perdition. I haven't seen it in a few years but it was awesome the first time I saw it. But it, too, might not hold up on repeat viewings because of the ending. But it's still a solid movie.