Why didn't Matt Dillon have a bigger career?

Dally Winston is so fucking hot dude

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He did all right; probably did a lot more producing than acting.
 
I always remember an angry critic writing “matt dillon smiles like the guy who finally got the joke a minute after it was told”

but I think he did pretty good. Most of his characters were kind of wise ass, douchey types so maybe he got typecast to a degree
 
I feel like Vince Vaughn took some roles I could've seen Dillon in.

That might however just be because of You me and Dupree. A film in which it's hard not seeing Vaughn in Dillon's role because of him having much better chemistry with Owen. The chemistry between Dillon and Owen in that movie is pretty nonexistent.

True, though I'd argue that chemistry aside, it's a pretty entertaining, overlooked comedy. Michael Douglas was sort of perfect in his role, as was Wilson. Early Seth Rogen film appearance too.
 
I'd say his career was actually sort of huge throughout the 80s and 90s. Not some Cruise-level star but consistently getting big roles and starring in interesting movies. It was only after the early 2000s that he started to fall off a bit. Wayward Pines, unfortunately, did not bring him back. But I think he's got some upcoming stuff that might get him back in the mix. Asteroid City, for instance. Hopefully he got along well with Wes Anderson. You get in that guy's crew and you'll get plenty of work as he likes to bring in the same actors (Norton, Brody, Goldblum, Dafoe, Scarlet, Bill Murray, Schwartzman, etc)
 
Always liked matt dillon, specifically from outsiders/rumble fish/tex. His character was the best part of something about mary
 
Cliff Poncier in Singles. A total doofus that the guys in Pearl Jam made fun of. But he ended up with a prime Bridgette Fonda.

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True, though I'd argue that chemistry aside, it's a pretty entertaining, overlooked comedy. Michael Douglas was sort of perfect in his role, as was Wilson. Early Seth Rogen film appearance too.

Yeah I thought Douglas brought something extra that the film needed. He is definitely the best part. It's not a bad movie at all, just probably could've been better and needed to be cut a bit.

Douglas is just the type of actor who makes whatever movie he is in better. He can carry a supporting role to perfection but he can also carry a film as the lead extremely well.
 
It's also worth noting that sometimes they don't want to pursue higher goals. He did fine. Other actors did better but it's also significantly more investment of your time and lifestyle.

When you hear that actors like Brad Dourif own 7 houses across the US and he's a guy that you just see and say "oh, yeah, I've seen him before", you realize you don't have to be a mega star to be very successful.

A buddy mine married a celebrities sister prior to him blowing up, and one of his best friends is a guy you see pop up on television shows and whatnot, and they have a house flipping business. Youd recognize him guest starring on CSI or something. You'd think he's like struggling and trying to make it, but he just does it to help pay some bills on the house flipping, which is where he makes bank. He can just show up for a guest roles and get good money for little work. You don't have to be a mega star to make good enough money to be wealthy or just have a nice pile to invest with.
 
Yeah I thought Douglas brought something extra that the film needed. He is definitely the best part. It's not a bad movie at all, just probably could've been better and needed to be cut a bit.

Douglas is just the type of actor who makes whatever movie he is in better. He can carry a supporting role to perfection but he can also carry a film as the lead extremely well.

Well said. He‘s excellent in whatever you see him in.
 
He’s had a pretty big career.

He’s pretty much the lead or one of the top billed in everything he is in. Most people with casual interest in movies would know who he is. He’s received critical and commercial accolades. Most of his films from the 80’s through aughts arent forgotten and still get a lot of interest. He’s been doing it for over 40 years and he still gets big roles.

Basically, he wasn’t as big as a very very small and exclusive list of actors that started around when he did.
 
Had no idea his brother starred in The Blob remake until I saw it on Svengoolie a few years ago. Completely missed that film when it came out.
 
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