40. Steven Bauer as "Manny" in Scarface
He's acting better than Pacino in this movie, but he's obviously not as fun. If there was ever a competition as to who could say "mang" the best, he'd probably win.
39. John Cazale as "Stan" in The Deer Hunter
As if this movie wasn’t depressing enough, Cazale was dying of cancer while shooting this film. He also deserves credit for "Fredo" in the Godfather movies, but I seriously have something like 5 characters on this list from those two movies so I don't want them to dominate too much.
38. Vince Vaughn as "
" in Swingers Trent
I'm pretty sure most men my age, and hell, even most women have quoted
from this movie. Do you want to kill him? Of course you do, but that's what makes the role so fun. Trent
37. Tom Cruise as "TJ Mackey" in Magnolia
Cruise should team up with Paul Anderson more often. Cruise always plays roles that are supposed to be cocky but likable characters, here he plays a cocky detestable character that you sort of end up having an emotional attachment to. I don't think I've ever had an emotional attachment to Cruise in a movie, in fact, I usually cheer against him.
36. Steve Buscemi as "Carl Showalter" in
Here's another nominee for my Supporting Actor Hall of Fame. Every time he has a conversation with William H. Macy in this film it's immaculate.
35. Brad Pitt as "Mickey" in Snatch
This may have been the Brad Pitt role that converted me from being a hater. The difference between he and say, Tom Cruise, is that he actually plays characters whereas Cruise plays himself.
34. Harvey Kietel as "The Wolf" in Pulp Fiction
His role may not have been that big, but when he's on this screen it's a lot of fun. Of course, almost this entire movie is a lot of fun.
33. Burt Reynolds as "Jack Horner" in Boogie Nights
Before this film, Reynolds' career was pretty stagnant. Gone was the moustached guy from fast car movies of the late 70s and early 80s. I can't think of a better way for him to make a comeback than an adult movie director, especially a classy one.
32. Mark Whalberg as "Dingman" in The Departed
It's crazy that Markie Mark has found at least two great roles (the other being Dirk Diggler) in his career.
31. James Caan as "Sonny" in The Godfather
Caan isn't the greatest actor but he came to play in this film. If he wasn't outshined by some of the greatest actors ever here, he may have won an award and probably not had to do that Rollerball movie.