Comedy, perhaps more than any other genre, dynamically reflects its era. What once brought laughter decades ago can, for contemporary viewers, range from uncomfortable to profoundly offensive. As social and cultural perspectives evolve, so does our collective sense of humor, often leaving beloved comedic films struggling to find their place. This re-evaluation compels us to critically re-assess their quality and continued relevance.
This critical lens isn’t about censorship. Instead, it’s a natural reflection of changing societal norms and a heightened awareness of issues like consent, respectful representation, and ethical portrayals. The ‘rules and expectations’ of filmmaking shift, and specific portrayals once deemed acceptable now seem ‘unsettling, disturbing, or even insulting to particular identities.’ The raw humor of yesteryear, especially that which targets specific groups, often ages ‘like milk,’ losing its appeal.
Join us as we embark on a critical journey through 12 comedy movies. Despite initial success, these films have simply ‘aged poorly’ and are now ‘tough to look at’ through a contemporary lens. We will explore specific elements challenging modern sensibilities, from blatant racism and casual misogyny to troubling ethical ambiguities. We’ll discuss why these once-cherished titles now feel ‘out of sync with the current generation.’
1. **Sixteen Candles (1984)**John Hughes’ directorial debut, ‘Sixteen Candles,’ is celebrated as an ’80s essential’ and a ‘classic coming-of-age comedy,’ starring ’80s icon Molly Ringwald. Referenced ‘several times in other forms of media,’ its place in popular culture is undeniable. However, the film is now recognized for its ‘offensive material’ and a notable ‘lack in both quality’ when viewed today.
One glaring issue is Long Duk Dong, a Japanese exchange student. His portrayal is ‘just one Asian stereotype after another,’ with an ‘exaggerated accent and gong sound effects.’ This caricature was so problematic that ‘many Asian Americans later claiming American classmates would taunt them with his quotes.’ The film’s ‘racism’ is arguably its ‘most obvious problem,’ making Long Duk Dong ‘wildly offensive,’ nearly a ‘parody of racism itself.’
Beyond racial caricatures, ‘Sixteen Candles’ also exhibits a deeply troubling ‘cavalier about non-consensual ‘ attitude. A disturbing scene involves a character who ‘brags about all the ways he would ‘violate’ his passed-out girlfriend.’ This, coupled with ‘characters discussing making the most of a lady who’s below the affect,’ is ‘not handled like a foul thing.’ The film’s ‘ethical issues’ and ‘casual consent’ violations ‘would horrify modern audiences,’ as it fumbles the topic without condemnation. This leads to ‘moral ambiguity’ not ‘applicable for a comedy that is meant to show a lesson.’ It makes the film ‘a powerful watch’ today.
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2. **Breakfast at Tiffany’s (1961)**’Breakfast at Tiffany’s’ holds a distinguished place as an ‘iconic American classic’ and ‘one of the most influential motion pictures of Hollywood’s Golden Age.’ Audrey Hepburn’s ‘iconic performance’ ‘remains enchanting,’ and the ‘playful rom-com helped to usher the style into the trendy age.’ Yet, despite cinematic merits, the film is ‘hampered by excessive racism’ that has made it ‘now deemed controversial.’
The primary source of controversy is the ‘portrayal of I.Y. Yunioshi, a Japanese character who Mickey Rooney, a white man, plays.’ Rooney’s performance involved ‘prosthetics designed to suit Japanese caricatures,’ a choice met with heavy protest ‘by Japanese people and other Asian nationalities.’ This character is explicitly described as a ‘blatant assortment of racist stereotypes,’ making the portrayal ‘even more inexcusable’ and contributing to the film’s ‘glaring flaw.’
Modern viewers find these ‘scenes so jarring they completely disrupt the film’s romantic atmosphere and sophisticated charm.’ The character of Yunioshi ‘serves no essential plot function beyond providing comic relief through racist imagery,’ which makes the ‘portrayal all the more poorly intended.’ While ‘casual racism was sadly part of ’60s culture,’ ‘Breakfast at Tiffany’s went method too far,’ significantly damaging its reputation and rendering it ‘unwatchable.’ Its ‘artistic merits’ clash with its ‘deeply problematic representation.’
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3. **American Pie (1999)**The 1999 film ‘American Pie’ was a pivotal cultural touchstone that ‘helped to kick off a franchise’ and contributed significantly to ‘the raunchy comedy pattern of the 2000s.’ It explored ‘the awkwardness of uality’ with a ‘stock-standard plot about dweeby excessive schoolers attempting to lose their virginity.’ While the movie ‘nearly works’ as comedy, it is unfortunately riddled with ‘poisonous parts which have precipitated it to age poorly.’
A substantial issue lies in the film’s overtly ‘one-sided view of its uality,’ characterized by a heavy ’emphasis solely on male want.’ Female characters often serve ‘primarily as objects for male fantasies rather than fully developed individuals.’ This pervasive objectification contributes directly to a broader problem regarding consent, as the film is structured around ‘treating intimate encounters as conquests rather than connections.’
Perhaps the most infamous and deeply problematic scene involves ‘a lady being filmed with out her consent.’ This ‘casual disregard for ladies is a disgusting relic, particularly since it’s performed off for laughs.’ Such an act ‘would likely be considered illegal invasion of privacy by today’s standards,’ making ‘Fashionable revisits of American Pie principally lead to frustration.’ Despite its potential as ‘a humorous intercourse comedy,’ these ‘poisonous parts’ ultimately cause it to ‘miss the mark by a large margin,’ making it ‘disappointing.’
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4. **Never Been Kissed (1999)**’Never Been Kissed,’ starring Drew Barrymore, remains ‘held in excessive regard by viewers of a certain age’ and is considered ‘a quintessential film for older millennials.’ This romantic comedy centers on Josie, a reporter who ‘must infiltrate a highschool to learn teen tradition’ by going undercover as a student. While it possesses ‘all the hallmarks of a basic rom-com,’ it is plagued by ‘one very large and evident downside’ impacting its watchability today.
The central problematic element involves the blossoming romantic affection 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.’ This creates an incredibly uncomfortable and ethically dubious dynamic, where a teacher is depicted as being attracted to someone he perceives as a minor. The film then makes the situation even more jarring when Sam ‘alludes to being upset once he finds out she’s actually of age.’
His dialogue profoundly underscores their initial connection: ‘“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’ and significantly ‘makes their eventual romance feel coercive rather than charming.’ The film’s ‘re-assessment following the #MeToo movement’ critically highlighted this issue, making the central romance feel ‘so jarring and unsettling that Never Been Kissed is unwatchable at present.’ It stands as a prime example of a film undermined by a ‘problematic’ romantic premise.
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5. **Ace Ventura: Pet Detective (1994)**’Ace Ventura: Pet Detective’ is widely acknowledged as ‘without doubt one of the motion pictures that made Jim Carrey a family identify,’ thanks to his distinctive physical comedy. Carrey’s portrayal of the ‘titular goofball’ tasked with recovering ‘the beloved mascot of the Miami Dolphins soccer group’ was a commercial success. However, the film is now recognized as ‘far from good’ and contains a ‘memorable’ twist ending, but definitively ‘for all of the improper reasons.’
The problematic core of the film’s aging lies squarely in its ‘climactic twist that treats gender identity and orientation as sources of horror and disgust.’ The ‘perpetrator is revealed to be disgruntled former NFL player Ray Finkle, who has spent years posing as Lt. Lois Einhorn, a feminine police officer.’ This shocking revelation triggers an ‘exaggerated revulsion from multiple characters,’ leading to a ‘comedic’ sequence where Ace ‘is shown vomiting and crying as he scrubs himself in the shower because he kissed a male.’
This ‘approach to LGBTQ+ themes reflects deeply problematic attitudes that cause genuine harm.’ The film ‘perpetuates dangerous stereotypes’ and explicitly ‘implies that trans individuals are humorous and that they deserve derision.’ Even if ‘it’s unclear if Finkle is actually transgender,’ the ‘film’s finale centers on humiliating them,’ with ‘the onlookers all vomit too’ after Ventura ‘exposes Finkle/Einhorn by revealing their genitalia.’ While ‘Carrey has since addressed these homophobic and transphobic undertones, stating… ‘In this day and age, it probably would not be done the same way,”’ the ‘ending ruins what’s an in any other case hilarious movie, and it’s onerous to get previous the evident faults.’
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6. **The Devil Wears Prada (2006)**David Frankel’s ‘classic comedy,’ ‘The Devil Wears Prada,’ vividly portrays the cutthroat world of high fashion through aspiring journalist Andy, played by ‘Hollywood sweetheart Anne Hathaway.’ She becomes an assistant to ‘one of New York City’s most successful yet toughest magazine editors,’ Miranda Priestly, brought to life by Meryl Streep. The film is often perceived as ‘a mixed bag when looking at it in a more contemporary setting,’ presenting strong female characters against a backdrop of problematic workplace culture.
On one hand, the film is justifiably lauded for being ‘carried by its female characters who exhibit ambition, passion, success and independence, alongside some killer dress sense and soundtrack.’ It powerfully showcases women striving in a competitive industry. 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,’ a significant concern for modern audiences re-evaluating its themes.
The context provides a clear example of this toxicity through Andy’s co-worker, Emily. 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.’ This harrowing portrayal highlights how such an environment demands extreme sacrifices. Even Streep ‘had a hard time mentally playing such a tough and merciless character,’ telling Entertainment Weekly, ‘“It was horrible! I was miserable in my trailer… I was so depressed! I said, ‘Well, it’s the price you pay for being boss.’”’ This admission underscores how the film normalizes and ‘celebrates’ professional dedication now recognized as detrimental and harmful.
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7. **Overboard (1987)**Garry Marshall’s romantic comedy, ‘Overboard,’ paired real-life couple Kurt Russell and Goldie Hawn in a bizarre love story. Russell, a widowed carpenter, felt scorned by Hawn’s entitled socialite. However, the narrative takes a profoundly problematic turn when Hawn develops amnesia after an accident. Russell then deceitfully pretends to be her husband, seeking revenge. This foundational deception creates an immediate ethical quagmire for modern viewers.
Indeed, ‘Overboard’ can easily be re-read as a ‘true crime story if not for the comedy classification.’ Russell’s character exploits a vulnerable woman, kidnapping her and subjecting her to ‘intense housetraining and initial mistreatment’ under the guise of teaching a lesson she cannot remember. The film frames this as justifiable comeuppance, profoundly misunderstanding the gravity of psychological manipulation and fraud. This narrative normalizes a profound violation of trust.
While the film attempts to mitigate the severity, and Hawn’s character verbally scorns Dean once her memories return, the two still end up together. This conclusion suggests that profound ethical breaches and blatant exploitation are mere bumps in the road to true love. It promotes a problematic message: deception and manipulation can lead to romance, and an absence of consent can be rectified by a later ‘happily ever after.’
Despite the undeniable ‘fantastic chemistry’ between Hawn and Russell, their magnetic screen presence struggles to overcome the unsettling foundation of the plot. Charming performances cannot mask the underlying narrative which normalizes coercion and a significant power imbalance. It clashes sharply with contemporary sensibilities regarding healthy relationships.
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8. **Cruel Intentions (1999)**A quintessential ’90s classic, ‘Cruel Intentions’ positioned itself as a ‘ual erotic thriller.’ It explored the machinations of two upper-class step-siblings, Kathryn Merteuil and Sebastian Valmont. Their twisted bet revolved around Sebastian’s ability to sleep with Annette, the headmaster’s virtuous daughter. While aiming for edgy allure, its core premise now reveals a disturbing and ‘immoral’ quality that challenges modern ethical standards.
The central wager, hinging on an unsuspecting girl’s ‘virginity status,’ immediately establishes a predatory dynamic far from comedic. The stakes were heinous: if Sebastian succeeded, ‘he gets to sleep with the step-sister like “he’s always wanted to”.’ This objectification of women, reducing them to pawns in a cynical game of conquest, is deeply ‘unethical.’ The film’s attempts at being ‘y’ fall flat, built on manipulation and disregard for female agency and consent.
What was perhaps intended as a dark portrayal of manipulative adolescence now reads as a troubling endorsement of toxic behavior. The narrative fails to condemn the characters’ actions, presenting schemes as thrilling rather than morally bankrupt. The movie’s ‘take on the concept of popular guys leading girls on all because of a bet’ is genuinely harmful. It illustrates a problematic worldview where exploiting others for gratification is an acceptable pursuit among the privileged.
Revisiting ‘Cruel Intentions’ today highlights its normalization of deceit and emotional exploitation in young relationships. While its aesthetic may hold nostalgic appeal, the ethical quandaries overshadow artistic merits. Modern audiences are increasingly attuned to consent and respectful relationships. This once-celebrated film serves as a stark reminder of how much perspectives on such narratives have evolved.
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9. **Big Daddy (1999)**Adam Sandler’s ‘Big Daddy’ introduced Sony, an unambitious law graduate who decides to care for his roommate’s five-year-old son, Julian. His initial motivation: to ‘impress his estranged girlfriend.’ While the film portrays a sweet bond between Sony and Julian, it is simultaneously riddled with deeply problematic elements, making it a ‘mixed bag’ through a contemporary lens.
The most glaring issue is Sony’s decision to take Julian under his wing. This act is not only ethically questionable but constitutes a serious legal offense. The film largely glosses over the fact that Sony ‘broke several child protection laws and kidnapped the child just to impress his girlfriend.’ This foundational act, played for laughs and character development, is profoundly difficult for modern audiences to accept. The narrative normalizes a profound violation of trust and child welfare protocols.
Furthermore, ‘Big Daddy’ contains several instances of humor relying on shaming and mocking. A ‘recurring joke where Sony shames and mocks his roommate’s fiancé for working at the chain restaurant Hooters’ is particularly jarring. Despite the character being a nurse, Sony consistently brings up her past employment for comedic effect. This displays a lack of respect and an outdated perspective on women’s career choices, proving mean-spirited rather than humorous.
Adding to problematic portrayals is a ‘flawed portrayal of a homeless person who is presented as mentally unstable for laughs.’ Such an approach trivializes serious issues like homelessness and mental health, reducing vulnerable individuals to comedic props. While heartfelt moments exist, these are significantly undermined by casual disregard for legal ethics, demeaning humor, and insensitive depictions. It has aged poorly for socially conscious audiences.
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10. **Sex and the City 2 (2010)**The second cinematic outing for Carrie, Miranda, Samantha, and Charlotte, ‘Sex and the City 2,’ transported its iconic quartet to Abu Dhabi. Intended as an escape, the trip quickly devolves into an ‘ignorant lens’ through which the film’s ‘outdated material’ is ‘just elevated.’ This sequel amplified the problematic aspects of the original series, particularly its biphobia and racist stereotypes, creating an ’embarrassing’ viewing experience.
The film’s most significant failing lies in the clash between its Western characters’ outlooks and the Middle Eastern setting. This cultural disconnect is not explored with nuance but for cheap laughs and harmful stereotypes. A cringeworthy scene sees ‘one character assume the Middle East still uses rubies and hasn’t discovered money yet.’ This culturally insensitive remark crosses the line from playful ignorance to outright offense, highlighting a profound lack of respect for the region.
Further exacerbating the issues is the depiction of the Western women ‘looking at the local women in religious headgear as though it was an exhibit.’ This portrays a problematic colonial gaze, reducing local culture and individuals to exotic spectacles. Such scenes underscore a broader pattern of cultural insensitivity and a failure to evolve past a narrow, ethnocentric perspective that permeates the narrative.
The original ‘Sex and the City’ series underwent critical re-assessment. The sequel, rather than learning, leaned into problematic elements with intensified lack of awareness. The film’s attempts at glamour and humor are consistently undermined by its profound cultural insensitivity and reliance on reductive stereotypes. This makes ‘Sex and the City 2’ a truly uncomfortable watch for contemporary audiences.
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11. **Bedazzled (2000)**Harold Ramis’ ‘Bedazzled,’ starring Brendan Fraser as the shy Elliot, presented an ‘exciting concept.’ It was a modern twist on the Faustian bargain: Elliot, hesitant to confess his love, is granted seven wishes by the Devil. While the premise held promise, the film’s execution ‘just goes about so many things terribly,’ undermining its potential with problematic humor and outdated stereotypes.
One glaring example occurs when Elliot wishes for success and love. This leads him to wake up living in Mexico, notably ‘with some facial prosthetics.’ The narrative then reveals that ‘in this reality, he makes his fortune smuggling drugs.’ This sequence is profoundly problematic, as ‘one of his wishes was granted based on a foundation of racist stereotypes.’ The casual association of a Mexican setting with drug smuggling and stereotypical physical alterations for comedy is deeply offensive.
The film’s reliance on such reductive and harmful caricatures demonstrates a profound lack of awareness regarding cultural representation. Instead of clever commentary, ‘Bedazzled’ defaults to tropes that reinforce negative stereotypes, diminishing any potential for sophisticated satire. What might have been intended as a dark comedic take on human desires becomes a frustrating exercise in outdated and culturally tone-deaf storytelling.
Despite the intriguing premise and charismatic performances, ‘Bedazzled’ ultimately fails to transcend its problematic material. The film’s dated comedic sensibilities and regrettable reliance on racist stereotypes make it a difficult watch today. Modern audiences are far more discerning about how different cultures are portrayed. ‘Bedazzled’ serves as a clear example of a film whose humor has curdled due to insensitivity.
12. **Waiting… (2005)**’Waiting…,’ released in 2005, aimed to offer a raunchy, behind-the-scenes look at the exploits of wait staff in a crummy restaurant. From its inception, the film was ‘deliberately offensive,’ mixing ‘raunchy humor with jokes which have expired of their cultural relevancy.’ While some controversial comedy can be deftly handled, ‘Waiting…’ sadly exemplifies how ‘raunchy humor can work and how it can fail too,’ ultimately landing squarely in the latter category.
One of the film’s most egregious issues centers on the main character’s explicit ‘lusts after an underage co-worker.’ This plot point, arguably inappropriate even upon release, is profoundly disturbing today. The normalization of an adult’s attraction to someone perceived as a minor, presented comically, reflects a severe ethical lapse. Modern audiences cannot overlook this, as it trivializes predatory behavior and undermines genuine humor.
Furthermore, the film features characters engaging in a crude and misguided ‘sport where they expose themselves to unsuspecting victims.’ While presented as rebellion, such acts constitute public indecency and harassment. What might have been intended as ‘misguided’ edgy comedy now registers as deeply uncomfortable and offensive. It demonstrates a casual disregard for personal boundaries and public decency that simply does not translate as funny today.
‘Waiting…’ stands as a stark ‘relic of a bygone era’ where its brand of shock humor and casual disregard for ethical boundaries were perhaps more tolerated. The film’s reliance on ualizing minors and normalizing harassing behaviors makes it exceptionally challenging to watch. As societal norms surrounding consent and respect have evolved, the humor in ‘Waiting…’ has not only ‘expired’ but has become actively repulsive.
As we conclude our journey through these 12 comedic relics, it becomes starkly clear that humor is not immutable; it’s a living, breathing entity, perpetually shaped by the evolving sensibilities of its audience. The discomfort these films now elicit isn’t about judging the past through an unforgiving present, but rather acknowledging the profound shifts in our collective understanding of respect, consent, and representation. These movies, once sources of widespread laughter, now serve as unintended historical documents, illustrating not only how far our society has progressed in its empathy and awareness, but also the enduring power of storytelling to reflect—and sometimes, regrettably, reinforce—the prevailing attitudes of an era. May our ongoing critical re-assessment continue to pave the way for comedies that not only entertain but also uplift and unite, reflecting the very best of our shared human experience.
