Why didn't Matt Dillon have a bigger career?

Saw him in the movie "The house the jack built"... was one of the most disturbing film i've seen...
 
Matt Damon stole his shine. In the end there can only be one Matt
 
He played a great racist in Crash. Seriously though, great role/acting.
 
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Rewatched the Outsiders the other day with son and pointed out how great this cast was.
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Thinking back on Matt Dillon, he stole the movie and for a while had it all, the looks, the fame, etc. Why did his career seem to stall? DrugStore Cowboy was so good.

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He was awesome in Something About Mary.....but never took that momentum forward.

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What's up with that?
There weren't really a lot of dimensions to his acting ability. He was more narrow than some of the other popular actors in his age group. "B list" guy.
 
I legit think the last thing I saw him in was Wild Things. He was so damn good in There's Something About Mary that I'm surprised he didn't get more comedy roles after that. Ben Stiller and Cameron Diaz both crushed after that movie.
 
He isn't an action star guy. He is a guy that gets a lot of quirky roles, usually not blockbuster ones. But he has been in a TON of great stuff and always kills it. Not to mention he has been around a LONG time, since 1979. Thats over 4o years.

Funny story. Since The Outsiders my wife had a huge crush on him. He was in NY doing promotion for Crash around 03-04. My wife and I had just watched Drug Store Cowboy a few nights earlier. We are in Manhattan at a place in the Village called "Caliente Cab Company". All of a sudden 3 handsome men get sat right next to us. Literally Banquette type seating. Its Johnny Depp, Peter Deluise, and Matt Dillon. My wife spit her drink out and gasped. They all laughed. We bullshitted a little with them, all polite and cool. Matt Dillon was born and raised in NY...he looks it and sounds it. That night when the wife and I got busy, I know she wasn;t thinking of me lmao....
 
He isn't an action star guy. He is a guy that gets a lot of quirky roles, usually not blockbuster ones. But he has been in a TON of great stuff and always kills it. Not to mention he has been around a LONG time, since 1979. Thats over 4o years.

Funny story. Since The Outsiders my wife had a huge crush on him. He was in NY doing promotion for Crash around 03-04. My wife and I had just watched Drug Store Cowboy a few nights earlier. We are in Manhattan at a place in the Village called "Caliente Cab Company". All of a sudden 3 handsome men get sat right next to us. Literally Banquette type seating. Its Johnny Depp, Peter Deluise, and Matt Dillon. My wife spit her drink out and gasped. They all laughed. We bullshitted a little with them, all polite and cool. Matt Dillon was born and raised in NY...he looks it and sounds it. That night when the wife and I got busy, I know she wasn;t thinking of me lmao....

You should have both fawned over the (other) dude from 21 Jump Street and ignored Matt and Johnny.

Peter did turn out more studly than you would expect for the spawn of Dom DeLuise. It's like if Wallace Shawn had a kid and it was Jon Bernthal.
 
You should have both fawned over the (other) dude from 21 Jump Street and ignored Matt and Johnny.

Peter did turn out more studly than you would expect for the spawn of Dom DeLuise. It's like if Wallace Shawn had a kid and it was Jon Bernthal.
Peter had just lost weight lol. He looked good. But Depp already started looking like a Pirate. Matt was one of the manliest dudes but still handsome at the same time. My wife started talking about us just watching Drug Store Cowboy and Depp told him that was his favorite film of his. We all got loaded, we were all drinking Rocket Fuels except Johnny. He drank Tequila straight.
 
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This would have been better if we asked why Kevin Dillon didn't have a bigger career.
 
He got to tap PRIME Cameron Diaz and he currently has an Italian supermodel wife. So his personal life is roses
 
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