Cinema is often considered timeless, but some films, even classics, don’t age as gracefully as one might hope. While feted on release, they now come across as heavy-handed, insensitive, cringe-worthy, or downright offensive. Many of them were well-intentioned, simply a product of the attitudes of their time rather than any mean-spiritedness on the filmmakers' part. Still, these dated elements make it harder to enjoy the movies, and can be a little jarring when one isn’t expecting them.
With this in mind, this list looks at someclassic films that have aged poorly. These films, despite their cinematic achievements, have elements that make modern audiences wince.A few of them leave audiences grappling with conflicting emotions: appreciating their artistry while acknowledging the problematic elements that undermine their legacy. One note here is thatD.W. Griffith’sThe Birth of a Nationis not listed. It’s a technically astounding and innovative picture that’s so morally repugnant and infamous it’s a stretch to call it a “classic” of any kind at this point.

10’You Only Live Twice' (1967)
Directed by Lewis Gilbert
“In Japan, men come first, women come second.” Although a big hit on release, the fifthJames Bond flickis a pretty lackluster one to revisit. It sees 007 (Sean Connery) faking his own death, infiltrating a Japanese crime syndicate, and uncovering a SPECTRE plot to start World War III using stolen spacecraft. The film is packed with elaborate action sequences, exotic locales, and larger-than-life villains, but itall feels rather hollow and unsatisfying.Some of the visuals, in particular, look incredibly dated.
The plot also takes a series of awkward and unnecessary detours, culminating in a chaotic and overstuffed finale. Indeed,You Only Live Twicefalls off in the second half, becoming more and more ridiculous. It’s all simply too cheesy and the usually stellar Connery is far from his A-game. The overreliance on gadgets borders on the cartoonish and most of the action sequences are decidedly dull. Finally, some modern reviewers have critiqued the scenes where Connery goes undercover as a Japanese man.

You Only Live Twice
9’Holiday Inn' (1942)
Directed by Mark Sandrich
“You could melt her heart right down to butter, if you’d only turn on the heat!” This romantic musical follows Jim (Bing Crosby), who opens a unique inn that operates only on holidays, and Ted (Fred Astaire), a charming dancer who complicates Jim’s romantic pursuits. It’s a fairly charming affair, boasting several memorable musical numbers likeIrving Berlin’s “White Christmas”, butsome of its scenes are insensitiveby today’s standards.
For example,one infamous scene involves blackface, and is jarring to see, very much puncturing the whimsical mood the film had conjured up in the scenes preceding it. This sequence has significantly marredHoliday Inn’s legacy. For instance, back in 2018, British Prime MinisterTheresa Mayreceived backlash when she declared it to be her very favorite Christmas movie. Plus, some of the film’s depiction of romance is also out of date, makingHoliday Innfeel very much like a product of its time.

holiday inn
8’The Palm Beach Story' (1942)
Directed by Preston Sturges
“That’s one of the tragedies of this life—that the men who are most in need of a beating up are always enormous.“The Palm Beach Storyisa screwball comedyabout love, marriage, and financial desperation directed by Preston Sturges, the brains behind movies likeThe Lady EveandUnfaithfully Yours. This one centers on Gerry (Claudette Colbert), a woman who believes her struggling inventor husband Tom (Joel McCrea) would be better off without her. She sets out to divorce him and find a wealthy suitor to fund his ambitions, leading to a series of absurd escapades in Palm Beach.
The rapid-fire dialogue and zany humor are enjoyable, but the jokes and visual gags don’t land as well as they do in some of Sturges’s other films. Plus,the gender dynamics are now understandably very datedand will make it harder for some viewers to become invested in the movie. The worst offense by far, though, is a woefully dated racial stereotype that seems to come out of left field. While it offers flashes of the director’s brilliance,The Palm Beach Storyultimately under-delivers relative to Sturges' finest, with this one sequence standing out in particular.

The Palm Beach Story
The Palm Beach Story follows the comedic journey of Gerry Jeffers, who plans to raise money for her husband’s invention by divorcing him and seeking the affections of a wealthy Florida magnate, J. D. Hackensacker III. As misunderstandings and whimsical encounters ensue, love and intentions are tested.
7’Chasing Amy' (1997)
Directed by Kevin Smith
“I’m just a guy who doesn’t know how to share.“Kevin Smith’sChasing AmyfeaturesBen Affleckas Holden, a comic book artist who falls for Alyssa (Joey Lauren Adams), a fellow artist who identifies as a lesbian. Their unconventional romance is fraught with complications as Holden struggles to reconcile Alyssa’spast with his own insecurities.The movie has many strengths, including some great jokes and a ton of heart, butthe dynamic between Holden and Alyssa has faced scrutiny in recent years.
Critics argue that the film perpetuates stereotypes, such as the trope of a woman “turning straight” for a man. The movie is certainly well-intentioned, but these ideas could have been explored with more nuance. “For anyone who watches the movie now and goes, like, ‘Ew, these sexual politics are … not very subtle’, you’ve gotta remember: It was made by a 26-year-old, 27-year-old guy, who really didn’t know anything and was learning in that moment,” Smith has sincesaid.

Chasing Amy
Chasing Amy is a romantic comedy-drama film by writer-director Kevin Smith. Following the viewpoint of comic artist Holden McNeil (Ben Affleck), the movie focuses on his hopeless romantic attachment to a fellow comic artist who happens to be a lesbian - and his best friend’s attempts at voicing his disapproval. The film explores the complex layers of love and what forms it takes.
6’Animal House' (1978)
Directed by John Landis
“Fat, drunk, and stupid is no way to go through life, son.” This raucous college comedy became a cultural phenomenon on release and remains one of the most highly-regarded comedies of the ’70s. Following the misadventures of the Delta Tau Chi fraternity, the film revels in chaos, pranks, and rebellion against authority. Its anarchic humor and larger-than-life characters, led byJohn Belushi’s iconic performance as Bluto, brought it instant classic status.
However,the film’s humor often comes at the expense of women and minorities.For every winning joke about politics, Vietnam, or the college experience, there are several juvenile ones. There are also some cringe-worthy conversations about sex and what some of the students will do to get it. Plus, the scene where Bluto spies on nude female students is uncomfortable to watch. Despite its cult status and influence in shaping the college comedy genre,Animal Houseis certainly not perfect.
Animal House
5’Rambo III' (1988)
Directed by Peter MacDonald
“God would have mercy. He won’t.“Rambo IIIfinds the muscly hero (Sylvester Stallone) traveling to Afghanistan to rescue his former commander, Colonel Trautman (Richard Crenna), who has been captured by Soviet forces. The film is packed with explosive action sequences and a heavily patriotic tone that was emblematic of ’80s action cinema, butit lacks the heart or fun of the earlier installments.
Plus, themovie’s portrayal of the Afghan conflict is reductive, simplifying a complex geopolitical situation into a binary of good versus evil. This is coupled with a cartoony ‘the enemy of my enemy is my friend’ philosophy. While the action is decent (if a little soulless), its depiction of Rambo aiding the Mujahideen fighters feels uncomfortable given the historical context of the region. In fact, the movie opens with the words “This film is dedicated to the brave Mujahideen fighters of Afghanistan”, which is decidedly odd to read now, given all that has unfolded sinceRambo IIIcame out.
4’Driving Miss Daisy' (1989)
Directed by Bruce Beresford
“You’re my best friend.” This controversial Best Picture winner explores the evolving relationship between Daisy Werthan (Jessica Tandy), an elderly Jewish woman, and Hoke Colburn (Morgan Freeman), her Black chauffeur. Spanning decades, the film examines themes of prejudice and friendship, as well as America’s changing race relations. But despite a few heartwarming moments,Driving Miss Daisyis often seen as an example of a well-intentioned film that lacks the depth to tackle its subject matter fully.
Indeed,many have criticized the movie for presenting an overly sanitized view of racism. It’s reluctant to engage with the realities, making it rather toothless and saccharine. While this approach might have been effective in 1989, it feels tone-deaf now. A far better treatment of similar ideas can be found inSpike Lee’sDo the Right Thing, released the same year (though ignored by the Oscars). Finally, the repetitive scenes of Jessica giving orders to Hoke start to become grating after a while.
Driving Miss Daisy
An old Jewish woman and her African-American chauffeur in the American South have a relationship that grows and improves over the years.
3’Revenge of the Nerds' (1984)
Directed by Jeff Kanew
“You know, when you’re a nerd, you don’t have too many friends.“Revenge of the Nerdsbears some similar problems toAnimal House. This flick tells the story of a group of outcast college students who band together to take on the popular jocks and cheerleaders. Using ingenuity, pranks, and camaraderie, the nerds prove their worth and make a stand. The humor and archetypal underdog story made the movie a cult favorite.
However, modern viewers may find parts of the movie deeply problematic.Several gags, including an infamous scene of sexual deception, are now viewed as inappropriate, perhaps even offensive. On top of that, some of the characters are caricatures, some gags are nothing more than gimmicks, and a handful of jokes feel like they would have already been past their sell-by date when this movie premiered. The third act, in particular, starts to drag, with the jokes slowing to a trickle.
Revenge of the Nerds
At Adams College, a group of bullied outcasts and misfits resolve to fight back for their peace and self-respect.
2’My Fair Lady' (1964)
Directed by George Cukor
“The difference between a lady and a flower girl is not how she behaves, but how she is treated.“George Cukor(The Philadelphia Story,A Star is Born) directed this lavish musical adaptation ofGeorge Bernard Shaw’sPygmalion. It focuses on Professor Henry Higgins (Rex Harrison), a linguistics expert who wagers that he can transform Eliza Doolittle (Audrey Hepburn), a Cockney flower girl, into a proper lady of society.
While the music remains widely beloved,some respective reviews have taken issue with the movie’s treatment of misogynist and classist tropes.The gender dynamics and power imbalances can certainly feel uncomfortable at times, with Higgins' condescending treatment of Elizaoccasionallyy bordering on outright cruelty. The movie’s defenders would say that My Fair Lady critiques these ideas, while critics say it affirms them. Even in terms of entertainment value,My Fair Ladyseems a little bloated and overhyped, not always holding the viewer’s attention.
My Fair Lady
In 1910s London, snobbish phonetics professor Henry Higgins agrees to a wager that he can make crude flower girl Eliza Doolittle presentable in high society.
1’Breakfast at Tiffany’s' (1961)
Directed by Blake Edwards
“You call yourself a free spirit, a wild thing, and you’re terrified somebody’s gonna stick you in a cage.“Breakfast at Tiffany’s is an iconic movie, featuring a peak-stardomAudrey Hepburnas Holly Golightly, a Manhattan socialite with a penchant for parties and avoiding commitment. Her budding romance with aspiring writer Paul Varjak (George Peppard) unfolds against the backdrop of 1960s New York, freezing that era in amber. Hepburn’s style here continues to be referenced and emulated today.
Still, the plot is a bit slight, and the script doesn’t delve all that deep into Holly’s character. It was partly for this reason thatTruman Capote, who wrote the original novella, so disliked the movie. But the aspect ofBreakfast at Tiffany’sthat receives the most criticism today is the casting ofMickey Rooneyas a Japanese landlord named I. Y. Yunioshi. Film historianRobert Osbornehascalledthe character a “caricature” and “totally embarrassing”. Rooney’s exaggerated, stereotype-ridden performance unfortunately detracts from the film’s otherwise charming atmosphere.
Breakfast at Tiffany’s
Breakfast at Tiffany’s is a romantic comedy film by director Blake Edwards and is based on Truman Capote’s 1958 novella. The 1961 film stars Buddy Ebsen, Audrey Hepburn, Patricia Neal, and George Peppard. The plot revolves around Holly Golightly as she falls in love and the trials and tribulations that come along with it.