Top/Bottom 5 Movie Roles - Matt Damon

Here is where I pick a random actor or actress's Top 5 and Bottom 5 Movie Roles (I assume the post title gave that away).  This won't necessarily be the chosen actor or actress's best roles, but a combination of their best and my favorite.  In other words, if there is a tie, I'll go with my favorite.  Also, I won't actually be ranking them, they will be in a random order.  Lastly, this isn't these actor's or actress's best movies, but their best characters.  Let's get started:

Matt Damon

Top 5

Jason Bourne, The Bourne Movies - Come on, you knew this would be here.  In fact, other than Good Will Hunting, you could say that the first Bourne movie was what really got his career going, or at least bumped him up to stardom.
Mike McDermott, Rounders - I love this movie.  Maybe it was because I saw it while in college when the poker boom was happening, but either way, it was awesome.
Carol, 30 Rock - A TV role?  Yup.  But his part on 30 Rock proved how funny Matt is.  That and this video.
Will Hunting, Good Will Hunting - The first time anyone really noticed Matt was with this movie.  People still quote "How 'bout dem apples" to this day.
Donny, Eurotrip - He was only in this forgettable comedy for about a minute, but look at him down in that picture.  How awesome is that?  This movie was worth watching just for his character, and the good news is that it was at the beginning and you can stop watching after that.

Bottom 5

Linus, The Ocean's 11 Movies - It's either that he is somehow the third most attractive person in the cast (no homo) or that his character is so whiny, I just did not like this role for him.
Bob Tenor, Stuck on You - Have you ever seen this piece of garbage?  Matt and Greg Kinear are conjoined twins and a lot of dumb happens.  No thank you.
Benjamin Mee, We Bought A Zoo - Was this movie cute?  Not really.  Was Matt good in it?  Not really.
Sully, The Departed - His performance wasn't that bad, it's just that I was pulling for Leo the whole time and he got shot in the head, so it was quite nice when Matt got his comeuppance also, even if I still didn't like his part.
Wilhelm Grimm, The Brothers Grimm - Another piece of garbage.  What made him take this part?  Was it the chance to work with Heath Ledger?  I hope so, because it couldn't have been the script.