10 Hit Comedy Movies That Have Aged Like Milk

Comedy is a fickle genre, and many films don’t stand the test of time. These hit comedy flicks didn’t just age poorly, they aged like milk. The subjective nature of comedy makes it challenging to pull off. Conflicting tastes mean that even the most beloved comedy movies have plenty of detractors. This is exacerbated when the movie has problematic elements.

Though movies like Blazing Saddles manage to court controversy while maintaining a good reputation, other films are far too clumsy with their messaging. Even well-meaning comedies can age poorly as time passes them by, and they become antiquated. What was acceptable in the past may not be acceptable today, instantly dating a film in the worst ways.

Unfortunately, some of the most poorly-aged comedy films have no such good intentions in mind. They brazenly punch down at marginalized groups, and make light of very serious issues in society. It’s okay to humorously examine a dark topic, but it must be done with tact and legitimate care. Anything can be funny if it’s done right.

It’s important to note that this list is limited to hits only, so it concerns comedies that were successful upon release. Though many of these films got poor reviews at the time, that didn’t stop audiences from flocking to theaters in droves. As with most controversial films, most of these comedies were criticized for being problematic when they were still new.

Crocodile Dundee (1986)

Crocodile Dundee is one of the highest-grossing comedies of all time, but it has largely faded into the background. The fish-out-of-water film banks on the charisma of Aussie Paul Hogan and his unique mannerisms. It places a bushman from the Outback in New York City, and finds laughs from the clash of cultures. Unfortunately, it also tries to get laughs from transphobia.

One particularly egregious scene sees Dundee sexually assault a trans person, humiliating them in front of a crowd of people who cheer him on. With so much else to work with, there’s no reason for the movie to take such a petty pot-shot at a marginalized group. Crocodile Dundee has aged about as well as a carton of milk left in the hot Australian sun.

American Pie (1999)

As a sex comedy from the 1990s, it stands to reason that American Pie is a problematic mess. However, the franchise-launching box-office smash is actually not as offensive as many other films on this list. It borders on parody, and is a clever inversion of the teen romps that came in the decade prior. Unfortunately, it’s sunk by one particular moment.

Jim invites the new foreign exchange student over to study, and surreptitiously attempts to film her changing clothes. Though the moment is ultimately played as a humiliation for Jim, Nadia is likewise exposed to the entire school. American Pie almost hits the mark, but its flippant cruelty leaves a sour taste in the mouths of modern viewers.

Ace Ventura: Pet Detective (1994)

Jim Carrey is an all-time comedy great thanks in large part to his early films. Ace Ventura: Pet Detective is one of Carrey’s signature hits, and it shows off the best of what the Canadian funnyman has to offer as a performer. The film is a 1990s classic, but has several moments that are best left in the past.

The biggest issue with the film is the central mystery, and it’s revealed that the antagonist is actually a man posing as a woman. Ace Ventura perpetuates anti-trans stereotypes, and features an extended sequence that mocks people with disabilities. Many other jokes in the film are still hilarious, but the climax makes it a difficult watch in the modern day.

Sixteen Candles (1984)

Filmmaker John Hughes is remembered as the master of the ’80s teen flick, and many of his movies are still beloved today. While most of his works have groan-worthy sequences, Sixteen Candles is one hit that is practically unwatchable in 2026. The coming-of-age film handles a lot of teen issues with class, but is insensitive in other areas.

It makes light of sexual assault, treating unwanted advances as one big joke. However, the most glaring issue is the portrayal of the character Long Duk Dong. He’s a collection of racist Asian stereotypes and doesn’t even fit into the looser cultural norms of the ’80s. Such blatant racism was as inappropriate 40 years ago as it is today.

Shallow Hal (2001)

The movies of the Farrelly brothers define ’90s comedy, but the same cannot be said for the 2000s. Shallow Hal is a cinematic disaster that somehow became a massive financial hit in 2001. It’s no surprise that the movie has aged like milk, largely because it was already spoiled by the time it hit theaters.

Jack Black plays a shallow bachelor who falls in love with a woman after he suddenly begins seeing her as thin instead of overweight. Gwyneth Paltrow spends most of the movie in a fat suit, and the film takes ample opportunity to poke fun at obesity. The ham-fisted message about inner beauty is totally overshadowed by just how offensive the movie is. There’s nothing funny about Shallow Hal, so it is forever defined by its problematic elements.

Big (1988)

Tom Hanks is best remembered for his dramas, but his early comedies are an integral part of his legacy. Big is arguably his best ’80s movie, but it has some glaring issues that don’t hold up in retrospect. Hanks’ character is a child that is magically transformed into adulthood. The problem is that he still has a youth’s mind.

He begins to form a relationship with an adult woman, including implied sexual encounters. This poses far too many ethical questions in a film that already has a somewhat mean-spirited concept at heart. Big is still a classic, but it comes with a ton of asterisks and content warnings for modern viewers.

I Now Pronounce You Chuck & Larry (2007)

I Now Pronounce You Chuck & Larry is a prime example of a poorly-aged comedy hit that didn’t have to be. The Adam Sandler and Kevin James vehicle doesn’t have the intellect to handle such a complex issue, so the goofball comedy resorts to blatant homophobia at every turn. There’s a kernel of an idea in there that is never explored.

Considering the fact that gay marriage was not legal nationwide in 2007, I Now Pronounce You Chuck & Larry is quite insensitive to a real issue that affected millions. Add in many, many gay-bashing jokes, and the entire film is rotten to the core. Sandler isn’t known for his political correctness, but the 2007 blockbuster is still beyond the pale.

Get Him To The Greek (2010)

Get Him to the Greek is an odd specimen because it’s a hit comedy that is soured by real-life circumstances. The film does feature a scene that plays unwanted sexual advances as a joke, but it’s relatively mundane otherwise. Contemporary reviews show mild praise, and the movie has only aged poorly in retrospect.

A major plot point of the movie concerns a hostile and sexually aggressive label executive who is played by Sean “Diddy” Combs. That storyline is made doubly gross by the fact that Combs is guilty of such behavior in real-life. What’s more, co-star Russell Brand is also embroiled in his own sexual assault accusations. It makes Get Him to the Greek a tough watch.

Never Been Kissed (1999)

Rom-coms frequently age poorly, but rarely do they spoil quite like Never Been Kissed. The Drew Barrymore smash-hit sees her play a journalist who goes undercover at a high school. She’s an adult, so it’s only natural that she might fall in love with the hunky English teacher. The fact that he reciprocates those feelings is where things go wrong.

Sam Coulson believes that Josie is underage, but is willing to allow such an inappropriate connection to form. Even worse, he’s initially quite disturbed when he learns that she’s actually of age. The whole thing is icky from start to finish, and isn’t nearly as cute as the filmmakers thought it would be. Though it’s less than 30 years old, Never Been Kissed is a dinosaur.

Revenge Of The Nerds (1984)

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Revenge of the Nerds is the poster child for ’80s sex comedies that treat women like props and make light of absolutely horrific scenarios. Because the movie is a certified blockbuster, it is even grosser than many of the lesser-known offenders of the decade. It’s supposed to be an empowering comedy that sticks it to the jocks, but it makes its heroes look like criminals.

Perhaps the worst moment in the movie comes when a woman is tricked into having sex with someone else. It’s played for laughs, but is a textbook example of sexual assault. The misogyny and racial stereotyping seem tame in comparison, but it all adds up to make Revenge of the Nerds the ultimate poorly-aged comedy hit.