Top/Bottom 5 Movie Roles - Adam Sandler

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:

Adam Sandler

Top 5

Billy Madison, Billy Madison - All I will say about how much I like this movie is that my fantasy football team is named Nudie Magazine Day.
Happy Gilmore, Happy Gilmore - Every time I see this movie again, I always laugh at how ridiculous Julie Bowen's haircut is (she plays the blond mom on Modern Family).
Bobby Boucher, The Waterboy - Was Bobby Boucher a dumb character?  Yes.  But as a whole, this movie was pretty funny and one of the last times Sandler made a decent film.
Barry Egan, Punch-Drunk Love - Ah yes, this flick.  Adam's first go at a drama.  And you know what?  He was pretty damn good.  Surprisingly so.  I saw this once and didn't like it, but that was probably because he was so convincingly not funny that I totally missed at how good of a job he actually did.
Nicky, Little Nicky - I know, this movie was really terrible, but for some reason I like it.  I can't explain why, but it's funny to me and I don't know why.

Bottom 5

Everything Else He Has Ever Done - Seriously, everything he has done outside of a couple of movies, the rest of his movie career is garbage, especially the last decade or so.  It seems that every single one of his movies lately follows the same script - pick a hot love interest, go to an exotic locale, and make a bad movie.  How is he still getting work with his string of crap?  I honestly don't know anyone that has gone to see one of his movies since 2000.