By which I mean is still funny, and has a minimal amount of jokes which aged poorly (not stuff that aged poorly from stuff they couldn't have known about, such as a joke about someone dying in a certain way, but then someone later died in a similar way, but aged poorly due to how problematic they are).
The main joke of Blazing Saddles is that racism and racists are real fucking stupid.
You know you couldn't make a movie like that today. The chuds would get too embarrassed. Also, whatever happened to the animated remake they were doing?
you wouldn't be able to make blazing saddles today because people would see it and say 'hey this is just blazing saddles this is already a movie'
I wish people would react that way to all the mediocre remakes of good movies, actually
Shaun of the Dead was released 17 years ago. I like Hot Fuzz better, but that was released 14 years ago, so it doesn't quite fit your criteria unless you're a libertarian.
Mel Brooks's movies make a point of being outrageous and raunchy, and not all the jokes age well, but at least he's usually on the "right side of history" (e.g. making fun of nazis, racists, etc.)
Going even further back: I like Buster Keaton's movies. However, the gender roles are a bit old-fashioned (e.g. the hero saves the girl, and there aren't many proactive female characters) and every so often there will be one brief-but-very-racist joke. Charlie Chaplin's movies are better and I can't think of very many that have obviously racist jokes, although I can understand a person being unable to watch his movies knowing that in real life he was a creep around teenage girls. Harold Lloyd's Safety Last is fun, but again, very traditional gender roles, and one brief-but-very-antisemitic scene with a Jewish pawn shop owner. Don't bother with the rest of Harold Lloyd's feature-length movies.
(e.g. making fun of nazis, racists, etc.)
KLAUS IS A MORON WHO ONLY READS THE NEW YORK POST
Dr. Strangelove or: how I learned to stop worrying and love the bomb
Bonus points for tricking Slim Pickens into thinking he was making a serious war movie, hiding every other part of the production from him.
How did they convince him that the movie where he sits on top of a bomb, waving his hat like it's a rodeo is a serious movie?
Kubrick butted heads with George C. Scott throughout the production; Scott wanted to play everything straight while Kubrick wanted more humour. Kubrick tricked Scott by getting him to perform over-the-top takes, which he said would not be used in the final film, as warm-up practice takes. Many of these takes ended up in the final cut, leaving Scott feeling angry and betrayed, and swearing never to work with Kubrick again (he came around later and admitted they made for a better movie).
Kubrick no doubt pulled similiar tricks with the bomber crew to get the shots he needed.
You're going to have to answer to the coca cola company.
The Big Lebowski is still good and its problematic moments are realistic/character flaws iirc.
Wes Anderson movies age pretty well.
Fargo is still good.
Haven't watched any in a while but I bet Jackie Chan stuff holds up.
Smoke Signals is still good.
Also seconding Monty Python and Mel Brooks
It's a little less than 15 years old, but Burn After Reading has aged exceptionally well given the recent ineptitude of the :cia:
Blazing Saddles has a couple of poorly aged pieces but is mostly ok. The Producers is still great in both versions, except for "keep it gay" in the musical which is a bit of a stereotype.
I still laugh hardest when Dom Deluise yells "WRONG" full blast into the megaphone
I always thought it was a celebration of gayness but maybe that's just me.
It's hardly the most offensive bit ever, but the slur and the tone makes me feel like it's definitely laughing at queer people, not with them.
Nobody's mentioned Monty Python yet -- or, closely related, Fawlty Towers. There's a lot of good British comedy. Off the top of my head: Mr. Bean, Yes Minister/Yes Prime Minister, and Look Around You are a few other shows I love.
American sitcoms I love include the first 8 to 10 seasons of The Simpsons. I'm also always trying to sell people on Mission Hill, a short-lived animated sitcom created by former Simpsons showrunners Bill Oakley and Josh Weinstein.
I want to say Yes Minister is a documentary, but honestly if I could press a button and make the UK government and Civil service half that humane and competent I'd mash it so damn hard.
Airplane, maybe?
It's been a while so I might be wrong but I don't remember anything problematic
I think one or two things here and there might have become problematic but it's mostly okay.
The "jive translator" scene definitely didn't age well.
Either Spaceballs or Robin Hood: Men in Tights
Edit: And The 'Burbs introduced me to the band Circus of Power, so there's that.
They could've done better in her first appearance. But subsequent appearances of her are much better.
I don't like how in season one the camera keeps zooming in on the outline of her penis as if to highlight how weird/gross it is. It's one thing when the characters are transphobic because, like, they're shitty people - that's the point. But when the camerawork is transphobic, it's hard to imagine the transphobia's supposed to be viewed critically.
But I agree with CthulhusIntern that she's better in the later seasons.
