10 Classic '90s Movies That Have Aged Terribly, Including Pretty Woman

Each of these films has significant merits, in one way or another. From Academy Award winners to tremendous box office hits, the 1990s were full of fantastic stories that have become surprisingly hard to watch in the decades since. Some of this is based around treatments of marginalized groups, while other issues are caused by weak technological shifts. Granted, social morals change all the time, and the bulk of these films were not trying to do anything especially incendiary upon release. Thirty years in the future, it is possible that audiences will look back on some of the biggest hits of 2026 with a more critical eye, finding details that might seem innocuous now as overwhelmingly offensive. How history assesses these changes in storytelling is something that can only be realized in hindsight. And some of the 1990s classic films that appear on this list are still able to be enjoyed to some extent. However, these specific details make that a lot harder, especially for those who might view these films today for the first time.

Ace Ventura: Pet Detective

Jim Carrey remains a tremendous talent, and Ace Ventura: Pet Detective was among the actor's fantastic 1994 breakout hits. However, despite the rich comedy and the fantastic work that Carrey does in the central role, the film has aged poorly for a notable plot point near its end. In the film's reveal, Ace discovers that Lois Einhorn is actually a transgender woman, having transitioned from Miami Dolphins player Ray Finkle. This discovery is treated as a punchline, and Ace is comically and cartoonishly disgusted by the fact that he previously kissed Lois. Featuring an exposition of Lois' genitals, the film's depiction of trans characters was offensive even upon release, but has only grown more so in the years since. While there are still things to enjoy in Ace Ventura, it is difficult to get past these offensive moments being played for comedy.

American Pie

American Pie was a phenomenon upon its release in 1999. The hilarious comedy captured the social tensions and pressures around teen boys attempting to lose their virginity with great wit and a strong cast, launching an enormous American Pie franchise. While there are some issues to be had with its depictions of masculinity and objectification, certainly, the core of the film is mostly heartwarming. However, one particular moment that is played for laughs, involving the exchange student Nadia, has aged especially poorly. In the film, while Nadia is changing in his room, Jim broadcasts the footage to the entire school. This invasion is seen as a silly prank, and Nadia becomes the one who is eventually punished for it, being sent back to the Czech Republic. All the while, Jim's only real punishment is his embarrassment.

Chasing Amy

Kevin Smith is an incredibly important director, especially known for the self-aware, thoughtful humor that he brought to relatable, metatextual conversations in films like Clerks and Mallrats. The filmmaker's third film, however, tried to bite off a little bit more. More dramatic and thoughtful than Smith's previous works, Chasing Amy, which features both Ben Affleck and Matt Damon, was initially released as a surprisingly open-minded look at lesbian relationships. However, as time has gone on, the central, straight and white framing of that story has grown progressively more uncomfortable. While the film was daring and mature for its 1997 release, the choice to frame the film around a straight man entering into a relationship with a lesbian woman and looking to change her has not aged well. While outdated in many of its approaches, Chasing Amy still at least had its heart generally in the right place.

Analyze This

Analyze This was a strong comedy hit, built around a premise that was strikingly similar to HBO's The Sopranos, which began airing only two months earlier. Starring Robert De Niro and Billy Crystal, the film focused on a Mafia Don who finds himself in need of a psychiatrist. While funny and sometimes thoughtful, the film's framing of therapy is strikingly outdated. De Niro's Paul Vitti goes to see Crystal's Dr. Ben Sobel, but keeps it a rigid secret, as it goes against the masculine presentation that is a part of his organized crime image. Some of the ways this is expressed are funny, while others are now incredibly difficult to watch. One line in particular, where Vitti says "If I talk to you, and you turn me into a f**... I'm gonna kill you", is framed as comedic, but now comes off only as ugly and offensive.

Blank Check

A fun cult classic, Blank Check is an entertaining story about an 11-year-old named Preston Waters who, through a series of fortuitous coincidences, winds up with $1 million in cash. The fantasy plays out from there, with Preston buying everything his heart desires. Where the film takes an especially disturbing turn is at its end. FBI agent Shay Stanley, who was played by an actor who was 31 years old at the time of production, shares an unsettling kiss with the lead and tells him to seek her out when he comes of age. This is a darkly twisted moment in an otherwise endearing and charming little movie, even if Blank Check doesn't frame it as one. Imagining the same scene with the genders reversed highlights exactly how uncomfortable the ending is in a way that has aged especially poorly.

Johnny Mnemonic

Johnny Mnemonic is a very interesting, but very dated, look at the cyberpunk genre. Released in 1995 and based on a short story by William Gibson, the progenitor of the genre, the movie starred Keanu Reeves as a data courier who must remove corrupted information from his head. The visuals are ugly, and the depictions of cyberspace have since become incredibly dated. Johnny's capacity for data implanted directly into his mind begins at only 80 GB, a volume that was considered enormous upon release, but seems laughably minuscule now. There are still some things to enjoy in the film, but it becomes harder to watch with every passing year. Clunky and often ugly, Johnny Mnemonic struggles to hold up against any modern eyes.

Pretty Woman

Pretty Woman was a huge hit upon release, and helped to launch Julia Roberts as one of the biggest and best stars in Hollywood. Framed as a Cinderella story between a rich businessman and a sex worker, it captured audiences' hearts with its unusual romance. With that considered, the whole premise is built around an enormous imbalance of power between Richard Gere's Edward and Julia Roberts' Vivian. His taking her and reshaping her is shown as aspirational and often even romantic, but has grown to feel controlling and objectifying. The film becomes harder to watch over the years for its treatment of sex work, as well as for the uncomfortable kind of relationship that grows between the two leads.

Never Been Kissed

Initially considered one of Drew Barrymore's best movies, Never Been Kissed tells the story of a young-looking 25-year-old copy editor who takes on a job to go undercover in high school in order to write an ambitious piece. The setup is fun, and the depictions of 1990s high school remain entertaining. What makes the film so hard to watch today, however, is the core romantic relationship that brews between Barrymore's Josie and her English teacher. The two have strong chemistry, but that is what helps to make their relationship and budding romance feel so unsettling. Josie's teacher believes her to be only 17 years old, which makes his clear attraction to her difficult to stomach. Even though he discovers she is actually much older later on, this dynamic makes the core romance of Never Been Kissed harder to watch with every passing year.

The Lawnmower Man

The Lawnmower Man, a very loose adaptation of one of Stephen King's popular stories, has some merits. The ambitious premise saw a simple man taken for government testing, in order to have his intelligence augmented with VR tools. While unsettling for its depiction of learning disabilities, the film's main issue is its visual effects. While ambitious for the time upon release in 1992, the science fiction horror of the movie has grown to look horrendous in the years since. The visuals attempt to depict cyberspace creatively, but the final results have grown to look ugly, ineffective, and confusing. Today, despite decent central performances by Pierce Brosnan and Jeff Fahey, The Lawnmower Man really only works as a campy bit of dated science fiction.

American Beauty

American Beauty is a stellar film, and won the Academy Award for Best Picture after its release in 1999, but is much harder to watch today. The bulk of the film is focused on Kevin Spacey's Lester Burnham becoming tired of his life and undergoing a striking midlife crisis. The most uncomfortable feature of the film, however, has to do with Lester's obsession with his daughter's 16-year-old friend, Angela. While the film's approach to this material is mostly thoughtful, many of the uncomfortable sexualizations presented about Angela only grow more difficult to watch with time. Regardless of the various difficulties in viewing American Beauty today, the film still has merit. While dated in its very male-centric outlook and much harder to watch in 2026, there are still several features to appreciate in this classic 1990s movie.