Some of these films are plagued with humor that feels outdated or feature protagonists who would likely be unappealing to current viewers. These movies would undoubtedly require significant modifications to address their most glaring issues before they could resonate with today’s audiences. Though the ’90s gifted us timeless classics like “Clueless,” “Jurassic Park,” and “The Truman Show,” not every popular film from that decade has aged gracefully. Here are those that haven’t.

Take “My Best Friend’s Wedding,” for example. Its humor isn’t particularly offensive, and the plot—centered around Julianne (played by Julia Roberts) who tries to rekindle a romance with her best friend Michael (Dermot Mulroney) as he is about to marry Kimmy (Cameron Diaz)—still strikes a chord. Looper even ranks it among the best romantic comedies ever. While it remains watchable, it likely wouldn’t achieve the same success if released as a new film today.

In the present day, Julianne’s actions would be recognized as stemming from internalized misogyny. Her animosity towards Kimmy lacks justification, making her an unsuitable protagonist for a 2026 romantic comedy. The narrative would likely lead to audiences championing Kimmy and criticizing Julianne. Since the story revolves around Julianne, the film would lose its essence if produced now.

Julianne has always been a selfish, antagonistic character. She suddenly decides, after years, that she is in love with her old friend. She then works hard to sabotage his wedding after he calls to tell her the news and invite her. She interferes in a genuinely loving relationship and attempts to break up Michael and Kimmy rather than simply admit her feelings to Michael privately. Julianne was still likable to 1990s audiences despite this, and that’s probably due in large part to Julia Roberts’ natural charisma. As well, Kimmy is 8 years younger than Julianne and Michael; she comes from extreme wealth, she’s conventionally gorgeous, and she has a sweet disposition. 

Today, Julianne’s distinct jealousy and resentment toward Kimmy would be identified for what it is — internalized misogyny. She has no legitimate reason to despise Kimmy, and for this reason, she wouldn’t be an acceptable main character for a rom-com in 2026. The film would likely go viral with audiences celebrating Kimmy and scolding Julianne, and because the film is about Julianne, it simply wouldn’t be the same movie today.

Wes Anderson is a much-loved director among cinephiles, and has collected his own sect of devotees. Anderson has a filmmaking style unlike any other working director, with a natural gift for visual storytelling. Anderson’s best films, including features like “Moonrise Kingdom” and “The Life Aquatic,” combine interesting stories with his distinct atmosphere, but not all of Anderson’s films feel as timeless or unimpeachable as others. 

“Rushmore” is one of Anderson’s earliest pictures. The film follows a 15-year-old kid named Max Fischer (Jason Schwartzman) as he befriends a wealthy older man named Herman Blume (Bill Murray) and romantically pursues a new teacher at his high school, Rosemary Cross (Olivia Williams). Blume is also interested in Cross, and as a result, finds himself at odds with Max in increasingly strange ways.

Obviously kids should be given a certain amount of grace when it comes to bad behavior, partially because their brains are still developing. Max, however, behaves like a Batman villain-in-training for most of this movie. He is a teenager, yet constantly hits on a fully grown woman. Because this script was written by two men (Wes Anderson and Owen Wilson), Rosemary finds Max’s overtures to be cute and impressively audacious. 

In real life, this woman would be filing a restraining order. Especially after Max cuts the brakes on her boyfriend’s car. This kid is frankly dangerous and unwell, and only Anderson would think this was a cute idea for a movie. Thankfully, it’s unlikely he could get away with it now, given society’s better-developed understanding of gender dynamics. The age difference and Max’s creepy insistence should have always been a problem, even in the 1990s.

“Ace Ventura: Pet Detective” is the kind of movie that people often reference by name, largely when discussing the filmography of Jim Carrey, who stars as the titular character. Many still quote its most famous line (“alrighty then!”) with its over-the-top delivery, but very few get into the nitty gritty details of the movie itself. Carrey’s breakout film launched a mini-franchise that is barreling toward obsolescence, despite Carrey’s interest in making a third installment of Ace’s adventures as the animal-savvy private detective. Everything about the movie that works comes from Jim Carrey’s comedic talent.

While it’s meant to be a fun, goofy film about a pet detective looking for a missing dolphin, “Ace Ventura: Pet Detective” actually has a fairly dark history. The movie’s plot concerns the missing mascot for the Miami Dolphins football team, and animal captivity is probably not something a comedic film would want to address in a post-“Blackfish” world. 

More importantly, the film takes an unabashedly transphobic approach to Sean Young’s post-op trans woman character, Lt. Lois Einhorn. Ace Ventura is disgusted, in retrospect, that she kissed him and expressed romantic interest before her trans identity was revealed. His reaction is despicable and frankly not funny, and it’s hard to imagine it was funny even when the movie first came out. Yes, even considering its “parody” roots in a previous — and somewhat better aged film — “The Crying Game.” Ace is also generally sexist, physically aggressive, and rude. He would not be a remotely supportable protagonist in 2026.

When a performer, especially a comedian, reaches a particular level of material wealth, they may lose their ability to do the kind of work they did at the height of their career. When it comes to comedy, relatability is essential, and it’s very difficult for exorbitantly wealthy comics to both relate to the majority of their audience and be relatable to that audience. Adam Sandler is a very, very wealthy man, whose net worth easily exceeds $400 million, and as such, he’s simply not the trailblazing comedian he once was. He spent most of his career dividing fans and critics, with some thinking he’s hilarious and others entirely unenchanted by his sarcastic characters and comedic idiosyncrasies.

 “The Waterboy” is an outlier for Sandler, a film that represented a transition in his career from angry guy to rom-com lead. It’s also not a movie that could be made today. Partially because of Sandler’s diminished ingenuity in the comedic arena, as explained above, but for other reasons as well. The movie follows a kind, simple man from a small town in Louisiana named Bobby Boucher who makes a living as a water boy, until a Coach Klein (Henry Winkler) sees his natural talent for brawling and makes him an outside linebacker. 

Bobby is unbelievably naive, and this, coupled with a truly ridiculous Louisiana accent and immature comportment from Sandler, gives the impression that Bobby hasn’t developed into a fully-grown adult who can handle high stakes situations like college football. The film requires way too much suspension of disbelief to be made today — and frankly, maybe we can stop with the Southern stereotyping, too.

Robin Williams is a comedic treasure and he will go down in history as one of the funniest people to ever live. He brought joy and vigor to everything he did, and “Mrs. Doubtfire” is no exception. One of Williams’ most memorable films, “Mrs. Doubtfire” centers on a married father of three named Daniel (Williams). Daniel loves his family, but as a freelance voice actor with a penchant for lateness and laziness, he doesn’t have a particularly stable lifestyle. His wife, Miranda (Sally Field), is fed up with his behavior and demands a divorce, sending Daniel out of the house and gaining full custody of their kids. Daniel, desperate to spend time with his children, disguises himself as Mrs. Doubtfire and convinces Miranda to hire “her” as a nanny.

Why couldn’t “Mrs. Doubtfire” be made today? Well for one thing, the star of the film, Williams, died in 2014, and there’s no living comedian who would be able to portray Daniel/Mrs. Doubtfire with as much depth and comedic brilliance as Williams did. For another, too much of the film’s humor hinges on Daniel’s crossdressing. 

Even though there is plenty of comedy in the movie that has much more to do with Daniel’s attempts to hide his identity from his ex-wife and children, and how to take care of his children while wearing a face full of prosthetics, a lot of the film’s jokes are just about how funny it is that a heterosexual, cis man like Daniel is wearing women’s clothing. Cross-dressing is a lot of things for a lot of people — an art form, an escape from the tyranny of gendered expectations, an essential part of their identity — and jokes about it from people who don’t care to understand fall flat.