Eraser. Thought it was cool. Showed it to the wife and she laughed hysterically at the whole movie. On the other hand, True Lies still holds up surprisingly well.-u/jeyise4954

Never Been Kissed The teacher becomes interested in Drew Barrymore’s character. She’s an adult but “plays” a high school student. -u/ridome9299

Revenge of the Nerds I mean, it was considered misogynistic and racist even by the standards of the day.-u/asoiahats

We saw Holiday Inn on Prime and said "It'll be a nice Bing Crosby movie with some Christmas songs," turned it on, and suddenly the cast is there in black face singing some of the most racist sh*t I've ever heard.-u/ridome9299

Breakfast at Tiffany's, specifically Mickey Rooney's role as Mr. Yunioshi. Mickey could have ditched the Japanese bit and played an American and it wouldn't have changed anything.-u/throwingplaydoh

Blank Check. An adult woman kisses the little boy on the lips for waaaay longer than I'm comfortable with. Imagine if the genders were reversed.-u/halel27443

Sixteen Candles. A lot of racism, casually addressing sexual assault, and later, an actual date rape.-u/jeyise4954

Red Dawn. Sure doesn't seem like the Russians would be capable of mounting any form of successful invasion of the US.-u/morgen_benner

Parody movies that dominated the mid-2000s and early 2010. You know, Scary Movie, Epic Movie, Meet the Spartans. Or any movies that tried to sell themselves as being written or produced by someone involved with the first scary movie.These movies will never age well because they are a product of that year: cramming pop culture references that happened in that specific production year into a movie. Sure you may have laughed at the movie when you saw them in the cinema because you understood what they are parodying, but someone in 10-20 years won't unless they have a Wikipedia tab open explaining what they are parodying.-u/Vaivaim8

Rambo 3. Where the Taliban are the good guys. Woof.-u/jeyise4954

G.I. Jane But the sequel has some good word of mouth going for it.-u/miltondelug

I think the movie Se7en has aged extremely well, all except for the part where Kevin Spacey said the pedophile he murdered deserved to die-u/scaryboilednoodles

The Polar Express. Those animations are nightmare fuel.-u/mesoxe4600

Back To The Future 2. They had so much hope for us back then.-u/primkolor

TEACHERS with Nick Nolte. Warm fuzzy teacher helps a student get an abortion. She is knocked up by his buddy, the gym teacher, and they all want to keep it quiet. This was just a side story to show how much this teacher cared about his students...so gross....-u/mesoxe4600

F*cking Garden State, man. Not for any socio-political reasons like all the other answers in this thread, but because it's so twee and early-2000's that it makes me dry heave to watch it now.-u/halloweenjon

Most Woody Allen movies.-u/oldgeek123

Tank Girl. Loved it as a kid - thought Lori Petty was SO COOL but man watching this movie as an adult was a 90-minute cringe fest-u/blacksweater

That one where John Wayne plays Genghis Khan-u/moondog8

Just saw this last night with the ladies in my family... Seven Brides for Seven Brothers. Those ginger fellas literally went one by one and abducted the hottest chicks from some town then held them hostage for months until through Stockholm Syndrome the women all fell for them.-u/ridome9299

Jim shares nude videos of Nadia on the internet in American Pie. Everyone just laughed it off.-u/ridome9299

No movie has aged worse than The Birth of a Nation. It was, and still kind of is considered a cinematic masterpiece in terms of performances, action sequences and cinematography. But uh, the KKK are the good guys and it's basically the most racist movie of all time.-u/halel27443

Seeing “The Weinstein Company” producer credit on any movie has not aged well.-u/mesoxe4600

The Rambo sequels. First Blood is still pretty good, but the rest were all propped up by Rambo doing stunts that were badass at the time and mild by today's standards.-u/heelspider

James Bond rapes Pussy Galore in Goldfinger-u/ridome9299