Mary was painful, but it was a comedy so I was still kinda laughing. but Misery ... that and Swingers were the first and only two scenes I could think of. I didn't think anybody else would nominate Misery, but ol' Iceblink beats me to it!
The scene in Boogie Nights where Roller Girl picks up a random guy to shoot a porno flick in the back seat of a limo, and it turns out to be a guy she went to high school with.
To add: the scene when they plan to rip off the guy freebasing cocaine and rocking out to "Sister Christian," while his Asian boy toy sets off firecrackers.
As bojendyk points out, there are a ton of "painful" scenes in that movie. Most of 'em in the 2nd half, during the "fall" of the heros.
That's a big reason why I hate Sondolz in general. I get very little pleasure or value out of any of his films. I just feel like he's shouting, "Look at me! Look at me! I'm different!" Shut up.
It's certainly not a "feel good" film and there are parts of it that are very uncomfortable to watch as well. But I just thought it was an interesting look at middle school/high school adolescents without the "John Hughes-esque deep down inside us preppies, stoners, jocks, geeks really have more in common than not" theme of most films about that subject.
Dollhouse is definitely stronger than Happiness, but I'm still a little underwhelmed by it. Yoss, have you seen Election?
It isn't a movie, but some of the things from The Office (more the UK version than the US version) are some of hte most painful things out there.
I was literally crying like I never had in a movie before and haven't since. Cracked me up completely. That didn't mean I wasn't cringing on the inside. When they showed it... I lost it.
Sure have....and absolutely love it. But (if I'm anticipating correctly) I think the two films, while possessing some similarities, are different as well......especially considering it's the teacher's (Broderick) viewpoint that is the focus of Election as opposed to the not-really-so-lovable-loser's viewpoint in Dollhouse.
-The scene where Flash has to stick his hand in that giant green thing in Flash Gordon. It was tough to watch when I was a kid at least. -"Squeal like a pig boy!!!!!!!!" Enough said. -The beginning of Kids when Telly is talking the virgin into giving it up. -All the scenes in Mallrats when Jeremy London is talking.
Another painful Boogie Nights scene. When Hoffman's character comes on to Wahlberg's character and kisses him.