Austin Powers.
It was hilarious back then but now, I can help but cringe through almost every scene.
One of my favorite teen movies was 16 Candles, which I loved as a kid, and looked forward to showing my son, when he got old enough.
The day came, and he watched it without cracking a smile. When it ended, he asked, “What did you think was funny? The underage binge drinking, the wanton destruction of a beautiful house, the Asian racism, or maybe it was the statutory rape? What exactly is funny about this movie?”
He ruins everything.
I guess I’ve only seen that movie once and it was about 30 or 40 years ago, I don’t remember a beautiful house being destroyed? I don’t remember any statutory rape? I guess it was just considered a normal sex scene back then? Either way I don’t remember that part either.
It was trashed during the party I think
OH GOD I just remembered Meet The Spartans exists.
To be fair this one didn’t age badly. It was already shit at release
Idk I either thought they were funny back then and still do, or I didn’t think they were and they still aren’t. My taste really hasn’t changed
The other day I wanted to watch a fun animated movie, and found that I’d never seen a Teenage Ninja Mutant Turtles movie that came out in 2007. Downloaded, put it on… and immediately greeted by the weinstien logo… then they had not one but TWO different Asian actors doing lines in the “broken Chinese accent.” Kinda ruined the whole movie for me.
Eurotrip - the whole dvd.
I clicked through rewatching some of it and it’s generically raunchy, like it was trying to outcompete the American Pie movie for sex references and topless women.
Edit: It can be very depressing in winter.
mi scusi
I don’t remember it being that bad and Scotty Doesn’t Know is a banger. Miscuzi!
Damon looked like he had a blast.
Yeah I don’t get the love of it. Parts of it are ok, but there is a lot of cringe.
Freddy Got Fingered
This movie just came up the other day. I drove a LeBaron at the time it was released. I’ll never forget “number one son”.
It’s always been an anti studio fuck you, and it’s brilliant in that regard
That is one of the biggest counter examples. Critical anger for daring to release the film. It’s considered a classic by now.
Some movies age like fine wine, some age like milk, Freddy Got Fingered aged like urine. It was sewage from the very beginning.
Oof yeah that’s a rough one
Shallow Hal is a pretty good contender

Isn’t the ultimate message of the movie wholesome though? I’ve never actually seen it.
The basic message is supposed to be but loses intent because of the fact it’s all fat jokes
Dear god. Never seen that, watched the trailer just now and can’t imagine that ever being funny.
I watched it when it came out, and I remember it being pretty meh, with very few (if any) laugh-out-loud moments, or even audible chuckles.
I can’t stand Jack Black, never found him funny.
Big “theatre kid” energy.
Bring It On, which is surprising.
Just a little too much casual rape dismissed as “digits slip.”
Anything with Adam Sandler
We’re just gonna pretend Wedding Singer isn’t a classic huh?
The only watchable Sandler movies are Uncut Gems, Hustle, and that one with the spider in space.
and that one with the spider in space.
Spaceman was a GREAT movie. I personally think it’s one of the best Adam Sandler movies ever.
I can’t tell if they aged poorly because I also hated them when they first came out.
Primarily because he’s about as funny as a erectile dysfunction
He’s at his most hilarious when he sings with the squeaky voice 🙄

It is an interesting question. Most comedy ages poorly, often not because it’s bad, but because the jokes are built on common assumptions of the era, and some of those are kinda shit.
Main exception being physical comedy. Some of those old silent films are hilarious, and just as funny now as when they came out 😂
Not having a language barrier, or anchor for that matter, makes a significant difference.
Like Mr Bean. I think the gags about cutting through photos of the royal family only get funnier with age.
City Lights is a great example of this but it is ALSO a great example of the opposite of this, specifically with all the jokes where drunk driving is the punchline
or universal situations
I rewatched Napoleon Dynamite last week and it holds up well IMO. So, not that.
The thing is it was a refreshing change when it came out. I thought it was the funniest movie I’d seen in years, bought the DVD when it came out thinking it was still great then when I tried watching it again a year later and it completely lost it’s luster. It’s like Juno, that one movie was great for a change of pace in an otherwise stale genre
Some movies only hit on the first watch. Once you know the gags, twists or ending its just “Yeah Ok.”
I hadn’t seen it until this year; it held up well, but the peak for me was the jumpcuts while they talk about Pedro’s bike
Nothing left for me to do but dance.
Bow to your Sensei!
Two that come to mind to me are Click and That’s my Boy. Both Adam Sandler movies of course. The first one is very queerphobic and sexist, and the second one is a story about pedophilia. Still surprised they managed to get Christopher Walken for Click tbh…
The sad dad in Click still elevates Click though.
I nominate “Dude, Where’s My Car?”.
I thought this was screamingly funny when it came out. It was the movie everyone quoted until “Napoleon Dynamite” came out. I tried rewatching it maybe a year or two ago and it’s aged like milk. Too much of the comedy relies on unhealthy stereotypes & tropes.
Don’t go dissing the original Hangover movie like that.
It actually holds up better when you interpret the guy walking out of, and back onto the closet, without either of them aware, in one of the first scenes, as demonstrating the theme of the movie.
I think dude where’s my car is a positive movie making light of negative anti light tropes though.
The movie is oft’ seen as a hidden metaphor for two male friends getting drunk and having a night of passion together. This is because it begins with them waking up with a hangover, on the sofa together, and a random naked man walks out of their closet in the background. Then walks back in when they bottle the question of “what did we do last night?” and refuse to revisit it.
It’s purposefully stupid so the tropes don’t bother me, the reason it was funny at the time was because the tropes hadn’t been established as much. It’s like saying old art is boring cause everyone does that now not realizing it was the OG. I still liked it and we watched it for movie night once and my at the time 19 and 21 year old kids liked it, we all quote it now.
ZULTAN!
Dude, what’s mine say?
Sweet! What’s mine say?
Dude! What’s mind say?!?
Sweet!.. What does MINE say?!
DUDE!!! what does MINE SAY?
SWEET! WHAT ABOUT MINE?!
SWWEEEEEEEETTTTT!!!
I got free-ticket coupons when the film melted in the middle of (an inconsequential scene in) Shaft. We chose to see Dude, Where’s My car?. I still want my money back.
It’s got two very quotable bits, but the rest I didn’t like in the slightest. Both leads have done better work!
Meanwhile Napoleon is like a fine wine.
Wish I could tell you off the top of my head, but if anyone is fond of badly aged comedy films (or just talking about them) there’s this great podcast/YT channel called This Aged Great focusing on 70s 80s & 90s films.
Edit:
- I think American Pie is a bit weird, not thwt funny given the subject matter, and contains really unpleasant elements
- Some of the high school movies of early 2000s were leaning into the template set up by their famous 80s predecessors, but i think people understood that the 80s films were purposefully trope-y. Whereas for the 2000s movies, they were treating it with reverence and it was like an unpleasant commitment to keeping alive a situation which had only ever existed in the real of fiction
that’s a great channel.













