10 comedy movies that have aged poorly

When it comes to genre filmmaking and writing, most eras have different rules and expectations, with certain portrayals being deemed acceptable given the times. It becomes easy to chart the decade in which a film was made when observing its style and story execution, especially genre codes and conventions. The most prominent genre that exemplifies this is the realm of comedy.

Previous decades and cultures had a different sense of humour that may not be appropriate when viewing through a more contemporary lens. What our parents found funny in their youth may not have the same effect on us today. It may be unsettling, disturbing or even insulting to particular identities. With inevitable changes in social and cultural perspectives, comedy has also evolved. Thus, comedy writers and comedians find their old material out of sync with the current generation. 

In turn, it can become difficult to watch a selection of comedy films that were made using an ‘outdated’ sense of humour, whether the film’s plot as a whole or certain aspects of it. This development makes it painful to cut a previous favourite from your watchlist due to its offensive material or re-assess its quality. However, there are those who argue such comedy shouldn’t be censored and restricted, claiming the medium can’t be tied down by societal norms.

Here are ten comedy films that fall into this outdated category, failing to hold up today. 

10 comedy movies that have aged poorly:

Sixteen Candles (John Hughes, 1984)

This classic coming-of-age comedy is John Hughes’ directorial debut and stars ‘80s icon Molly Ringwald as a high schooler whose 16th birthday is overlooked by her family. However, once she catches the attention of two classmates, things suddenly take an eventful turn.

Sixteen Candles is an ‘80s essential, referenced several times in other forms of media since its release. However, this iron clasp of nostalgia for the decade can’t conceal the film’s actual lack in both quality and its offensive material. For example, there’s Long Duk Dong, a Japanese exchange student whose traits are just one Asian stereotype after another, with many Asian Americans later claiming American classmates would taunt them with his quotes after the film’s release. Furthermore, there has been a re-assessment in deciding if Sixteen Candles condemns date rape, as one character brags about all the ways he would “violate” his passed-out girlfriend. No amount of quirky ‘80s fashion or background songs can outdo such attempts at humour.

The Devil Wears Prada (David Frankel, 2006)

David Frankel’s classic comedy follows aspiring journalist Andy, played by Hollywood sweetheart Anne Hathaway, who becomes an assistant to one of New York City’s most successful yet toughest magazine editors. Meryl Streep plays the cutthroat Miranda Presley, who eventually takes Andy under her wing in the journalism industry. 

The Devil Wears Prada is a mixed bag when looking at it in a more contemporary setting. On the one hand, the film is carried by its female characters who exhibit ambition, passion, success and independence, alongside some killer dress sense and soundtrack. However, the other hand draws attention to its celebration of a toxic work environment where staff work themselves to the point of damaging their well-being. Andy’s co-worker, Emily, is so committed to living up to the impossible standards of her job that she starves herself, works when sick instead of resting and eventually needs to be hospitalised. 

Streep also had a hard time mentally playing such a tough and merciless character like Presley, telling Entertainment Weekly: “It was horrible! I was miserable in my trailer. I could hear [the cast and crew] all rocking and laughing. I was so depressed! I said, ‘Well, it’s the price you pay for being boss.’”

Overboard (Garry Marshall, 1987)

Real-life married couple Kurt Russell and Goldie Hawn play a couple with a bizarre and unorthodox love story in Garry Marshall’s romantic comedy. Russell plays a widowed carpenter who is scorned by Hawn’s entitled socialite way of life. After Hawn develops amnesia following an accident, Russell pretends to be her husband to show her another way of life out of revenge.

If you haven’t already gathered from the synopsis, Overboard could easily read as a true crime story if not for the comedy classification. Russell’s character essentially exploits an unwell woman, kidnaps her and puts her through intense housetraining and initial mistreatment to teach her a lesson following an incident she doesn’t even remember. He does receive consequences for this disturbing series of events, as Hawn’s character verbally scorns him once her memories return. However, the two still end up together. The only thing that has the potential to redeem Overboard is the stars’ fantastic chemistry.

Ace Ventura: Pet Detective (Tom Shadyac, 1994)

Comedy legend Jim Carrey plays a pet detective who is tasked with finding the Miami Dolphins’ mascot, Snowflake the dolphin. Helping him in his investigation is Melissa Robinson, the team’s publicist.

Ace Ventura: Pet Detective has come under scrutiny recently because it negatively portrays trans people and cis-het people’s perception of them. The kidnapper is revealed to be a hitchhiker named Eric Finkle, who has undergone surgery to change his identity to Lois Einhorn in order to carry out his crime, who Ventura kisses in the film. After the detective pieces this information together, there is a ‘comedic’ sequence that shows him vomiting and crying as he scrubs himself in the shower because he kissed a male.

After Ventura then exposes Finkle/Einhorn by revealing their genitalia, the onlookers all vomit too. Carrey has since addressed these homophobic and transphobic undertones, stating (via Cheatsheet): “In this day and age, it probably would not be done the same way. There’s a learning curve for all of us.”

Cruel Intentions (Roger Kumble, 1999)

Two upper-class step-siblings, played by Sarah Michelle Geller and Ryan Phillippe, make a bet that the brother can’t sleep with the headmaster’s daughter, Annette. However, in an unexpected turn of events, Sebastian really falls in love with Annette.

Cruel Intentions is a quintessential ’90s classic for some reason. The film is marketed as a sexual erotic thriller when it’s just a disturbing and immoral porno. The two leads place a bet concerning an unsuspecting girl’s first time and ‘virginity’ status, with the stakes being if the step-brother wins and uses the target for sex, he gets to sleep with the step-sister like “he’s always wanted to”. Its attempts at being sexy just fall flat, with its take on the concept of popular guys leading girls on all because of a bet is one of the most unethical.

Big Daddy (Dennis Dugman, 1999)

Adam Sandler plays Sony, an unambitious law graduate who ends up taking care of the five-year-old son of his successful roommate with plans to impress his estranged girlfriend. When his original plan falls through, Sony bonds with the child and learns a new perspective on responsibilities. 

Another mixed bag, Big Daddy has some roughness in its overall diamond. While the bond that grows between Sony and the young Julian is sweet, comical and relatable, and the film has a heartfelt tone, the fact that Sony broke several child protection laws and kidnapped the child just to impress his girlfriend cannot be overlooked. In addition, the film has a recurring joke where Sony shames and mocks his roommate’s fiancé for working at the chain restaurant Hooters to make ends meet during medical school. It’s something he brings up every time he sees her, even though the character is now a nurse. There’s also a flawed portrayal of a homeless person who is presented as mentally unstable for laughs.

Sex and the City 2 (Michael Patrick King, 2010)

The second film adaptation of the hit HBO series sees Carrie, Miranda, Samantha and Charlotte head to Abu Dhabi when their lives get a little too harsh. The trip leads Carrie to reunite with a long-lost love. 

The original Sex and the City series has also been re-assessed in its outdated material, such as biphobia and racist stereotypes. In the second film, this ignorant lens is just elevated. The film’s setting and the characters’ outlooks clash too often to the point where it’s no longer funny but embarrassing. One scene sees one character assume the Middle East still uses rubies and hasn’t discovered money yet. Another is the western women looking at the local women in religious headgear as though it was an exhibit. 

Bedazzled (Harold Ramis, 2000)

Brendan Fraser plays Elliot, a shy man who is hesitant to confess to the woman he loves. After the Devil takes pity on him and grants him seven wishes, Elliot tries every opportunity to have his love become required. 

Bedazzled holds an exciting concept, especially portraying the Devil as a beautiful woman. However, it just goes about so many things terribly. One example is Elliot wishing to be successful and loved, leading him to wake up living in Mexico with some facial prosthetics. Not only this, but in this reality, he makes his fortune smuggling drugs. Essentially, one of his wishes was granted based on a foundation of racist stereotypes.

Breakfast at Tiffany’s (Blake Edwards, 1961)

This iconic American classic follows a cafe society girl who falls head over heels for a writer who has just moved into her complex. However, the past threatens to keep the two lovers apart. 

Breakfast at Tiffany’s is a landmark in American filmmaking and Audrey Hepburn’s iconic performance. However, the film is now deemed controversial due to its portrayal of I.Y. Yunioshi, a Japanese character who Mickey Rooney, a white man, plays. Rooney performed the part in prosthetics designed to suit Japanese caricatures, which were protested heavily by Japanese people and other Asian nationalities. Given that the character has no direct relevance to the story, this portrayal seems all the more poorly intended.

Never Been Kissed (Raja Gosnell, 1999)

Josie, an editor, goes undercover as a high school student to report on the lives of high school students. However, she struggles to blend in and is plagued by flashbacks of her real high school experience.

This romantic comedy underwent a re-assessment following the #MeToo movement, with critics and audiences double-checking the romance that blossoms between Josie and her teacher Sam. Josie becomes the object of Sam’s affection, even though he has every reason to believe she is an underage student of his and alludes to being upset once he finds out she’s actually of age.

He shoots himself in the foot with the statement, “What, you were hoping I’d be happy?” he says. “Because all of a sudden, I’d be allowed to be attracted to you?” This line implies an unsettling perception of his female students.