Scenes From ‘90s and 2000s Comedy Films That Seem Offensive Today

Society has evolved significantly in the past two or three decades. And, of course, these changes have affected pop culture, too. From movies to music and comedy, some of the things that were norms in the past are no longer the same. Most of them aren’t even acceptable anymore.

Source: Reddit

This includes scripted scenes that used to be hilarious but now make us cringe. We’ve compiled a list of these movie moments from comedies that didn’t last. We’re not saying these movies or shows should be cancelled, but these scenes from the 90s and 2000s are no longer valid today.

Never Been Kissed (1999) – The Weird Student-Teacher Relationship

The more we think about the 1999 movie “Never Been Kissed,” the more we realize it was such a weird film. Drew Barrymore portrays Josie, an insecure and timid copyeditor who goes undercover as a high schooler because she’s writing a story about young people.

Source: Twentieth Century Fox

She develops a special relationship with Mr. Coulson, her English teacher. She’s 25 years old, so this is not weird yet. But it’s strange because he doesn’t know that! Since he didn’t act on it, it’s technically OK, but he wants to, and that’s just creepy.

Pet Detective (1994) and Transphobia

We can’t imagine the outburst if a movie was released today and the villain was (forcefully) discovered to be a transgender woman, then the other characters responded by choking and throwing up. Additionally, it is implied that the character transitioned to escape being arrested for her crimes.

Source: Warner Bos.

That is absurd and feeds into prejudice toward transgender people. And we aren’t the only ones who think so. In response to criticism that his 1994 film Ace Ventura: Pet Detective was transphobic, Jim Carrey acknowledged that many of the jokes don’t hold up today.

Clueless (1995) – Josh and Cher’s Relationship Was Clueless

We’re sure that, just like us, many people didn’t think too much into it when we first watched “Clueless” in the 90s. But it looks like even the creators were… clueless. When you think about it, wouldn’t you agree Josh and Cher’s relationship was a little problematic?

Source: Paramount Pictures

If the movie were released today, we are almost certain people would have a problem that Josh and Cher end up together. Not only were they step-siblings, but Josh is in college, and Cher is still in high school and only 16 years old!

Bring It On (2000) – The Finger ‘Slip’ Scene

At the time it was released, “Bring It On” could be seen as a radical movie. It tackled important societal issues that you wouldn’t expect from a cheerleading movie, such as social tension, race, and cultural appropriation. But despite that, we wouldn’t consider it to be a flawless movie.

Source: Universal Studios

For instance, there is the infamous scene where Jan (Nathan West), one of the male cheerleaders, holds up his cheer mate Courtney but his finger happens to “slip.” What’s awful is that everyone just treated it as some sort of joke. We all know this wouldn’t survive backlash nowadays.

She’s All That (1999) – The Lame Transformation

Rom-coms are meant to be entertaining and light-hearted, but when we watch “She’s All That” again, one of the most memorable sequences makes us feel offended because it insults our intelligence. The story starts with a bet that a popular boy will transform a nerdy girl into a prom queen.

Source: Miramax Films

So, there was bound to be a dramatic makeover scene in such a plot. But Laney Boggs’ “before and after” feels more like “same and same.” The only real changes are that her glasses are taken off and she gets a haircut. Even the producers would cringe at that now.

Dazed and Confused (1993) – The Line About High School Girls

Although “Dazed and Confused” was Matthew McConaughey’s debut film, the director opted to expand his role because of his outstanding performance, giving the public a chance to see more of the future star. In fact, some of the actor’s lines from the 1993 film have become iconic.

Source: Gramercy Pictures

But the one about high school girls doesn’t hold up today. Saying “That’s what I love about these high school girls… I get older, they stay the same age” certainly didn’t stand the test of time. It makes sense in that context, considering McConaughey’s character is a douchebag.

American Pie (1999) – The Creepy Filming

Who doesn’t remember “American Pie”? The flick undoubtedly went beyond what a teen movie could get away with, but although there are undoubtedly many scenes in which things are taken too far, one in particular has not aged well. You probably didn’t notice at the time.

Source: Universal Studios

That’s the scene where Jim secretly records his classmate Nadia via a webcam. A scene like that would be unacceptable today. It turns out we aren’t the only ones who think so: Actor Jason Biggs who played Jim, also admitted that such a scene “would be unacceptable” nowadays.

Never Been Kissed (1999) – Rob Dating a 16-Year-Old

Did you find it odd that Josie went back to high school posing as an undercover reporter who developed a connection with her English teacher in “Never Been Kissed”? We did, too. But wait until we tell you that wasn’t even the weirdest part of the movie.

Source: Twentieth Century Fox

Rob, her 23-year-old brother, who had no reason to be there in the first place, returns to high school to assist his sister but soon develops feelings for a sophomore instead. Josie points out that the girl is 16 years old, to which he responds, “I know! And a gymnast.”

Love Actually (2003) and All the Body-Shaming

Nowadays, people enjoy watching “Love Actually” over and again, especially during the holiday season. But we hope the only thing they take from it is the importance of human connection the movie preaches about—not the constant body-shaming. People most likely didn’t pay much attention to it in 2003.

Source: Universal Studios

However, today’s viewers are less likely to laugh at mocking people’s bodies. The scenes where Natalie is referred to as “Plumpy” and the “chubby girl with “big thighs” (by a co-worker!) aren’t acceptable today. Not to mention Aurelia’s sister, who is subjected to body-shaming by her entire family.

Billy Madison (1995) – The Dodgeball Montage

Do you remember how believable the dodgeball scene in Billy Madison was? Everyone wondered how they made it appear like Adam Sandler was really hitting the kids with the ball. And in fact, he kind of did (well, sort of). The children were 6 years old and couldn’t read.

Source: Universal Studios

So, they had no idea what was about to happen. As a result, when Sandler’s character throws the ball at them, they are startled, and their reactions in the scene are actually real. For some strange reason, the parents of the child actors went along with it.

Miss Congeniality (2000) – The Eating Disorder Joke

Eating disorders are big issues today and many struggle with them, so joking about them wouldn’t fly. When a tomboy investigator Gracie Hart infiltrates the Miss United States pageantry, the stage is set for many jokes about the unrealistic beauty standards and the culture of pageants.

Source: Warner Bos.

However, some of those gags seem out of date and inappropriate now that eating disorders are more commonly discussed. Take, for instance, Sandra Bullock’s character saying that eating pizza shouldn’t be an issue because Miss Rhode Island will “throw it up anyway.” That wouldn’t hold up today.

She’s All That (1999) – When Laney Escapes Assault

“She’s All That” has another entry on this list. It may have been an OK movie, but it wasn’t without its flaws. Laney and Zack had a weird conversation toward the end of the high school movie where she tells him Dean tried to assault her after prom.

Source: Miramax Films

The problem is that her tone is totally off, almost normalizing what happened as if it wasn’t a big deal. Zack appears unconcerned, Dean escapes punishment, and this extremely serious matter is joked about. Dean only has one punishment—he does not hear his name announced during their graduation ceremony.

There’s Something About Mary (1998) – The ‘Hair Gel’ Scene

American romance comedy “There’s Something About Mary” was released in 1998 and was directed by Peter and Bobby Farrelly. There’s Something About Mary has many absurd, unforgettable scenes, such as the dog-on-sedative scene and the zipper incident, but the “gel hair” scene is by far the most popular.

Source: Twentieth Century Fox

It also seems to have aged the worst. Speaking to The New York Times, actor Ben Stiller said he didn’t believe any guy wouldn’t feel the semen drooping from his ear unless he had lost sensitivity in his ear. It just doesn’t seem realistic that Cameron Diaz’s character was so naive.

Wedding Crashers (2005) – The Midnight Scene

When you think about it, 2005 doesn’t seem too long ago, but that was about 17 years ago. Society has gone through significant changes since then, and the jokes that were funny in 2005 could raise eyebrows today. Well, something happened in 2005’s “Wedding Crashers” that isn’t so funny today.

Source: New Line Cinema

Do you remember the moment from Wedding Crashers where Vince Vaughn’s character is being attacked by his girl in the middle of the night, and she ignores him despite his desperate pleas for her to stop? No way that would happen today without raising red flags.

Legally Blonde (2001) – The Stereotype Moment

Even if the classic 2001 movie “Legally Blonde” has become synonymous with female empowerment, we must admit that it is not flawless when we watch it now. Did we hear you say “no”? Well, wait until you watch this scene in a new light.

Source: MGM

Elle Woods’ first “a-ha” moment in support of her client is based on a homosexual stereotype. Her justification is that gay men are more likely than straight men to recognize designer shoes, and she uses this “information” to trick the prosecution’s key witness into confessing that he has a boyfriend.

10 Things I Hate About You (1999) – When Kat Flashed Her Soccer Coach

The 1990s gave us some of the most memorable romantic comedies in history, and “10 Things I Hate About You” is one of them. That was mainly because of its talented cast, which featured Heath Ledger, Julia Stiles, and Joseph Gordon-Levitt. But that doesn’t mean it was perfect.

Source: Buena Vista Pictures

One scene we all forgot is when Kat wants to get Patrick out of detention. She starts an inappropriate conversation with her soccer coach. She speaks about his “package,” rubs his biceps, and then flashes him. The worst thing is that he stares at her a bit too long.

Shallow Hal (2001) – the ‘Fat Suit’ Cannonball Scene

Shallow Hal, a 2001 rom-com, has so many issues that we don’t think any scriptwriter would have the guts to suggest this movie to a big studio nowadays. The problem is that despite the movie’s theoretical insistence that “it’s what’s inside those counts,” they continue to make fun of overweight people.

Source: Twentieth Century Fox

Do you remember the moment when Gwyneth Paltrow, wearing a “fat suit,” cannonballs into a pool, splashing enough water to send a child to the top of a tree? The entire cast undoubtedly would have liked it if it had been one of the deleted scenes.

Garden State (2004) – The Manic Pixie Dream Girl

It may seem that all the movies from the 1990s and 2000s haven’t aged well with offensive or improper content. The 2004 comedy “Garden State” is not morally unacceptable, but the common perception of it has changed significantly since its release. The movie earned excellent reviews in 2004.

Source: Fox Searchlight Pictures

But nowadays, people can’t get over Natalie Portman’s portrayal of a Manic Pixie Dream Girl. Her character is a quirky, unrestrained girl whose main aim is to show the gloomy male protagonist how to live a more colorful life. This has become so overused these days that it’s boring.

Clueless (1995) – The ‘Cake Boy’ Moment

If you thought Josh and Cher’s relationship was the only strange thing in Clueless, wait till we remind you of this offensive scene in the 1995 film. As if it wasn’t enough that Murray was condescending while teaching Dione how to drive, he was also disrespectful to women in general.

Source: Paramount Pictures

And to the entire LGBT community. He begins by asking, “Are you b—— blind or something?” before stereotypical comments describing Christian as a “cake boy.” In Murray’s world, reading Oscar Wilde, listening to disco music, and admiring Barbra Streisand immediately qualify a guy as being in the LGBT community.

Soapdish (1991) – Transgender Issues

Although Hollywood still has lots to learn when it comes to diversity and representation, it’s safe to say the industry has come a long way in the past few decades. For example, take a look at this scene from the 1991 comedy “Soapdish”.

Source: Paramount Pictures

When it is found that Montana Moorehead was originally known as “Milton Moorehead, of Syosset, Long Island,” she is forcibly outed as a transgender woman. Her co-stars’ horrified and disgusted reactions make it clear why the scene hasn’t aged well. Society has changed a lot since then.

The Waterboy (1998) – Mocking Disabled People

Even while Adam Sandler’s kind of comedy is still not for everyone, his films have changed significantly over the past few decades, and it is impossible to deny that he has evolved considerably. His 1998 comedy “The Waterboy”, for instance, wouldn’t be so popular with viewers today.

Source: Buena Vista Pictures

He plays a socially awkward character in the movie, which follows the same concept as many of his earlier works: You can mock minorities and people living with disabilities as long as you hint that they’re people, too. Well, we don’t see stuff like this from him anymore. Rightly so.

She’s All That (1999) – Objectifying Women

1999 was over 20 years ago, and things have changed since then. The central message of “She’s All That” isn’t exactly a win for feminism. And the film makes it clear right away. Once Zack and Dean decide to take their degrading bet, they begin the demeaning process of picking their victim.

Source: Miramax Films

They pick on the “flaws” of a few of the ladies they objectify before settling on Laney Boggs. We all know how difficult it will be to change Laney into an entirely new person. She had to get her hair chopped and her glasses removed!

Jawbreaker (1999) – When Staging a Serious Crime

“Jawbreaker” starts with a popular girl’s three best friends accidentally killing her. Of course, this isn’t your typical family film, but the brutal kidnapping or the scene in which they discover the girl’s body in the trunk of their car aren’t the bits that wouldn’t be acceptable today.

Source: Sony Pictures

The most inappropriate part happened later when, while trying to cover their tracks, they make it seem like the young girl was attacked and murdered by a man. Such a joke would definitely not fly today, even if for a dark comedy movie. They got away with that.

Blank Check (1994) The Strange Kiss

Here’s another example of “How on earth did that get made?” In this case, it’s the 1994 movie “Black Check,” which recently went viral after someone rediscovered it and shared their thoughts on what happened in a particular scene. It was the moment the FBI agent kissed 11-year-old Shay Stanley.

Source: Twitter

Audiences in 1994 seemed not to mind this shocking scene, but it’s a different story these days. The unnecessary moment has been harshly criticized on social media. It’s not only inappropriate, but there’s the fact that it involved an actual 11-year-old boy. This should’ve been weird even in 1994.

Empire Records (1995) – One-Dimensional Female Characters

When “Empire Records” was released in 1995, it was an entertaining watch. Directed by Allan Moyle, the movie starred Anthony LaPaglia, Debi Mazar, Maxwell Caulfield, Johnny Whitworth, Rory Cochrane, Robin Tunney, Liv Tyler, and Renée Zellweger. But despite being a delightful watch, looking back makes us realize its many flaws.

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That’s especially when you consider its female characters. All three women are stereotyped — from the party girl with a golden heart to the innocent one and the damaged teen. They are all somewhat one-dimensional and flat, in contrast to the masculine characters who have their own inner journeys.

Love Actually (2003) – The Posterboard Scene

The scene in “Love Actually” where Mark secretly confesses his love for his best friend’s wife, Juliet, caused viewers to swoon when the movie was first released in 2003, but time and some critical thoughts have led many people to reconsider the significance of that “romantic” moment.

Source: Universal Studios

Mark’s actor, Andrew Lincoln, has even been quoted as calling his role a “weird stalker guy” and admitting that he was concerned about seeming creepy while filming. It took a while for viewers to catch on, but certainly, many people now find his character creepy.

10 Things I Hate About You (1999) – Kat Stratford’s Treatment

The fact that “10 Things I Hate About You” is driven by a strong young woman who is plainly capable of making her own decisions sets it different from other teen rom-coms of the era. However, Kat Stratford was essentially made into a villain for no reason.

Source: Buena Vista Pictures

That’s because characters of this kind were so uncommon at the time. She is intelligent, doesn’t listen to nonsense, and doesn’t always agree with the teacher. As it turns out, Kat flashing her soccer coach wasn’t the only strange thing that happened in this teenage drama.

Bring It On (2002) – The Bikini Car Wash

Audiences in 2000 were happy that the Toros had come up with a unique way to earn money to hire a choreographer, but now, 20 years later, some are upset with the way the scene was presented. High school students dancing in tiny bikinis…

Source: Universal Studios

…and spraying each other with soapy water seems kinda odd, doesn’t it? Although you may disagree, this is a “cheerocracy” rather than a democracy. Additionally, if you replay the scene in question, you’ll see a female wipe a car with her chest. That wouldn’t fly today.

Observe and Report (2009) – How the Date Ended

It’s unbelievable that this scene was ever given the go-ahead to be included in a film, let alone a comedy, of all genres. That’s the scene in “Observe and Report” where a mall cop named Ronnie (Seth Rogen) asks a salesgirl named Brandi (Anna Faris) on a date.

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She is obviously drunk when they get back to his apartment, but the following shot shows them in the bedroom, where he is awake and she is not. You get the drift, right? There’s no way you could convince us that this was OK in 2009, so it’s quite shocking.

American Pie (1999) – The Role of Stifler’s Mom

“American Pie” is featured again on this list, which is hardly shocking. More than two decades after the movie’s release, Jennifer Coolidge is still remembered for her portrayal of Stifler’s mom. That speaks to her acting abilities, especially given the few resources she had to work with.

Source: Universal Studios

The whole situation with her was funny 20 years ago, but when you pause to think about it, Stifler’s mom is a character whose sole purpose was to satisfy a lusty teenager. Jennifer Coolidge deserves praise for making it work, but people today prefer characters with more depth.

Mrs. Doubtfire (1994) – How Daniel Hillard Breaks the Law

Daniel Hillard’s actions in Mrs. Doubtfire seem justifiable to us because we are seeing the story from his point of view, but if we shift our perspective slightly, it becomes clear that he is acting inappropriately. He defies his wife’s wishes and goes against a court order.

Source: Twentieth Century Fox

He dresses as a woman and tries to surreptitiously raise his children—to whom he was a lousy father. Robin Williams is so fascinating in the film that we didn’t see it that way when we first saw it, but now things are a lot clearer and people are more analytical.

The Devil Wears Prada (2006) – The Unsupportive Boyfriend

In “The Devil Wears Prada,” Andy’s boss, Miranda, is the devil, but Andy’s lover Nate is a close second after putting her through hell. When the movie was released, most of us saw him as Andy’s stable partner from whom she drifts as she gets immersed in the fashion world.

Source: Twentieth Century Fox

Now, we can see him for the egotistical and unsupportive man that he is. Since it was Andy’s first job after graduating from college, she is expected to give it her all. Even though she only intended to stay there for a year, he couldn’t support her.

Can’t Hardly Wait (1998) – William’s Revenge

Since Mike Dexter from the 1998 film “Can’t Hardly Wait” is the jock fans loved to hate, we were never against the concept of William and his friends devising a payback plan to exact revenge for all those years of humiliation and public anguish.

Source: Sony Pictures

The strategy they devised to humiliate their aggressor, however, did not stand the test of time. Putting him to sleep with chloroform and posing images to make it appear as if he belongs to the LGBT community? It seems that in 1998, nothing could be worse than that.

Jawbreaker (1999) – The ‘Karen Carpenter’ Line

“Jawbreaker” wasn’t afraid to show how far it could go with its jokes. Well, not until people’s hahas turned to “oh no.” In 1999, the scene below may have worked, but it definitely wouldn’t make the final cut today. Courtney tries explaining they don’t have a problem.

Source: Sony Pictures

She was trying to divert attention by pointing to four girls who were sharing a little box of raisins and referring to them as the “Karen Carpenter table.” That statement seems incredibly inappropriate in light of the growing awareness of the severe effects of eating disorders today.

Singles (1992) – Janet Changing for Her Man

Now that we think about it, it’s funny that the movie “Singles” and TLC’s music video “Unpretty” were released in the same year since they both tell the story of a lady who wants the help of a cosmetic surgeon in order to please her lover.

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The woman in question is Janet in Cameron Crowe’s “Singles.” She has the most bizarre conversation with Dr. Jeffrey Jamison but ultimately chooses against having the procedure. Good thing the “change everything about you for a man” narratives are no longer popular with viewers today.

Chasing Amy (1997) – How a Community Was Portrayed

“Chasing Amy” is another example of a film that, although considered progressive when first released, hasn’t held up very well over time. And two decades later, it appears almost embarrassing (although that’s a good thing since it shows that society is still evolving, right?).

Source: Miramax Films

The movie received plaudits when it first came out for even broaching the issue. But it has since come under fire for how it represents the LGBTQ community, particularly women, who are depicted as being able to convert to heterosexuality when “the right guy comes along.”

Clueless (1995) – The Use of the R-Word

People nowadays have a low tolerance for the word “retarded,” and in recent years, we’ve heard big personalities like Lady Gaga and LeBron James publicly apologize for their usage of the word. So, yeah, Cher Horowitz would be bleeped if Clueless were remade in 2022.

Source: Paramount Pictures

She refers to everything she considers to be awful with the r-word throughout the 1995 film. Although certain sections of society still consider this to be “soft,” it just doesn’t fly today. In fact, numerous studies have been conducted showing why the r-word is a problem and should be stopped.

Billy Madison (1995) – The ‘Mammy’ Stereotype

We’ve already had one entry of Billy Madison on this list, but that wasn’t the end of it. Adam Sandler is a triple threat since his jokes have criticized the value of minorities, women, and persons with disabilities. Thankfully, Sandler is now doing better with his films and jokes.

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But films like “Billy Madison” will always remind us of his willingness to challenge stereotypes. The use of the “mammy” stereotype in Billy Madison’s maid Juanita, a loyal, dark-skinned caretaker working for a white household, has drawn criticism. Again, it was a different era, and things have changed since then.

Superbad (2007) – The Anti-LGBT Comments

Some of Seth Rogen’s blunders may be attributed to his youth because he began writing the “Superbad script when he was just 13 years old. Years after the film’s release, he acknowledged that it might not have been the best move. He admitted to “glamorizing” the anti-LGBT language.

Source: Sony Pictures

Especially those used by the protagonists in the 2007 box office hit. He even claimed that if he were to recreate the film, he would have to remove its “blatantly homophobic” gags. We all learn daily, and big ups to Rogen for admitting he was wrong and willing to change it.

She’s All That (1999) – Jesse’s Role

“She’s All That” has a problematic primary female character, and her sidekick isn’t any better. Just what is going on with Jesse Jackson? Although he is not part of the LGBT community, he is depicted in the movie as the stereotypical male best friend who is.

Source: Miramax Films

By the end of the film, he’s dating Zach’s sister. He can’t even enjoy a Twinkie since his “best friend” constantly tells him that he needs to lose 10 pounds by graduation. The poor child is constantly body-shamed. Goodness, Laney, just leave him alone!

I Now Pronounce You Chuck and Larry (2007) – The ‘Asian’ Minister

Picking just one scene from “I Now Pronounce You Chuck and Larry” to discuss on our list was difficult. The Wall Street Journal termed it “an insult” to LGBT people, straight people, people of all sexes and ages, African Americans, Asians, physicians, firefighters, insurance adjusters…

Source: Universal Studios

…postal workers and pastors, when it was initially released in 2007. Additionally, time did not help. Not only did the movie’s theme—two straight men getting married to receive a tax break—not hold up over time, but Rob Schneider’s use of yellowface to portray a stereotypical Asian minister wasn’t any better.

Varsity Blues (1999) – Limited Choices for Women

Most people associate Ali Larter’s portrayal of Darcy Sears in the coming-of-age sports drama “Varsity Blues” with her notorious whipped cream “outfit,” but that’s not the only part that we can’t stop thinking about. The fact that Darcy had few choices hasn’t really held up over time.

Source: Paramount Pictures

In 1990s comedies, many teenage girls had just two choices: be smart and attend an Ivy League school or get married to their lover and benefit from his success. We’re in a time where women are being made to realize they don’t have those two choices and can be more.

Bridget Jones’s Diary (2001) – Workplace Harassment

When “Bridget Jones’s Diary” was released in 2001, most people were unaware of what now seems practically obvious—Bridget was being harassed at work. And it was all done for fun. She received inappropriate texts from her employer, Daniel Cleaver, about her clothing and appearance in general.

Source: Universal Studios

The work atmosphere then became so unpleasant for her when their relationship broke down that she made the decision to quit. Although we somehow found humor in it back then, viewers nowadays are more informed. Workplace harassment is heavily frowned upon, so such a movie won’t fly nowadays.

Made of Honor (2008) – Fragile Masculinity

1990s and 2000s sitcoms and movies portrayed many unrealistic plots. For example, they made it seem like realizing you’re head over heels in love with your best friend just when they’re about to marry someone else is something that happens more often than it actually does.

Source: Sony Pictures

That’s the plot of “Made of Honor”. But the part of the movie that hasn’t aged well is the fragile masculinity of its male characters. For instance, there are many jokes about Tom being queer simply because he is playing a role at a wedding that is typically played by women.

A Cinderella Story (2004) – The Issue with Diets

“A Cinderella Story” was an OK movie, but if it were released today, it undoubtedly would require some editing since we are more conscious of the impact pop culture has on young girls now. There’s a strange way diets are represented in the teen movie.

Source: Warner Bos.

For one, the girls have eating disorders and are made fun of for it, which has drawn criticism from many fans. Sam is praised for taking anything she wants to eat. What kind of question “If given a choice, would you eat a rice cake or a Big Mac?”

Confessions of a Shopaholic (2009) – Rebecca Bloomwood’s Attitude

The timing of “Confessions of a Shopaholic” was erroneous. The wrong movie at the wrong time. People couldn’t empathize with the recession that the entire world was currently experiencing. Even though some people might appreciate seeing Rebecca Bloomwood’s antics now, there are other issues with the film as well.

Source: Walt Disney Pictures

The treatment of the debt collector is one thing that hasn’t made sense either back then or now. Even though he was only doing his job, when she eventually had enough money to pay him, she decided to do so in the most inconvenient way possible. In fact, in pennies!

Bride Wars (2009) – Portraying Women as Wedding-Obsessed

It was instantly clear even when it was released in 2009 that “Bride Wars” didn’t have the most nuanced female characters for a movie. The plot was basically about two childhood best friends who became sworn enemies, getting into a race of “who marries first.” Ugh.

Source: Twentieth Century Fox

The scene with Liv, played by Kate Hudson, might have aged the worst. After breaking into her boyfriend’s office in the middle of the workday, yelling at him in front of his coworkers, and forcing him to pop the question, she succeeds in getting what she wants in the end.

Rush Hour (1998) – The Stereotypical Jokes

The “Rush Hour” movies were undoubtedly great. While the majority of viewers didn’t find the racial gags in the 1998 comedy offensive, the Asian-American community wasn’t sure if the film represented an improvement in having an Asian protagonist or a regression due to the stereotyping.

Source: New Line Cinema

A few gags, like the one about the Panda Express or the one in which Detective James Carter tells Chief Inspector Lee that he wants to be acquainted with some of those Chinese girls because he needs a massage, are certainly now considered offensive after more than 20 years.

The Ugly Truth (2009) – The Inappropriate Introduction

In the 2009 comedy “The Ugly Truth”, Gerard Butler’s character Mike is portrayed as a masculine chauvinist. His character is meant to be the exact opposite of Katherine Heigl’s Abby in order for them to instantly dislike one another but gradually fall in love despite everything.

Source: Sony Pictures

But it’s not even the cliche plotline that we’re talking about. Given what we now know about workplace harassment and how serious it is, his inappropriate introduction of her could appear a little excessive. After all, there are many more ways to highlight his character’s true nature.

There’s Something About Mary (1998) – Normalizing Stalking

Stalking is an actual crime of power and control that is punishable by law. However, in romantic movies from the 1990s, stalking is something that you do when you’re in love—and if you can persuade your victim that your motives were good, you could even get rewarded.

Source: Twentieth Century Fox

Although most people turned a blind eye to the stalking in “There’s Something About Mary,” society has evolved. Now, more scrutiny has gone into how Ted’s behavior toward Mary is less romantic and more dangerous than it was 20 years ago. There’s nothing romantic about stalking. It’s creepy.

My Best Friend’s Wedding (1997) – How Julianne Treated George

Rupert Everett, Julia Roberts, and Cameron Diaz starred in the 1997 romantic comedy “My Best Friend’s Wedding.” It was easy to overlook some of the glaring problems with the actors’ roles in the movie because of their charisma. When you think about it though, Julianne (Roberts) isn’t a good person.

Source: Sony Pictures

But it’s not just because she unexpectedly realizes she loves her friend and doesn’t want him to be married, but also because of her treatment of George, mistreating him and abusing his kindness to her. George essentially serves as the LGBT best friend. We all overlooked it.

The Parent Trap (1998) – The Twins’ Separation

“The Parent Trap” is a 1998 American rom-com produced by Charles Shyer, who co-wrote it with Nancy Meyers, the movie’s director. The most unbelievable part of this movie wasn’t even when Annie and Hallie didn’t realize they were twins. It was ignoring the fact that they had the same face!

Source: Buena Vista Pictures

Lindsey Lohan played both roles. Parents Nick and Liz separated after the twins were born, deciding that it would be best to keep their children apart, live in separate countries, and never tell them that they were twins. Woah! Meyers and Shyer went wild here.

Knocked Up (2007) – Katherine Heigl’s ‘Killjoy’ Role

Seth Rogen and Katherine Heigl star in the 2007 American romantic comedy “Knocked Up,” which was written, co-produced, and directed by Judd Apatow. Heigl, the female lead, had some unfavourable things to say about the movie when speaking to Vanity Fair. And her comments weren’t exactly nice.

Source: Universal Studios

She said women were represented as “humorless and uptight” while men were depicted as “fun-loving” and “lovable,” making the movie “a little sexist” and her role a “killjoy.” She was forced to retract her comments, but many viewers now agree with her assessment that the film perpetuates negative female stereotypes.

Varsity Blues (1999) – How Billy Bob Was Treated

We’ve already referenced 1999’s “Varsity Blues” on this list, but the film’s flaws didn’t end there. Sure, Billy Bob became the hero getting the game-winning touchdown as the movie reached its end, but many viewers of the film today are unhappy with how the character was treated.

Source: Paramount Pictures

Especially throughout the other 100 minutes. Billy Bob was the movie’s clown, and of course, many of the jokes center around his weight, even though an unhealthy diet and his coach’s “win at all costs” mindset were essentially killing him. Not the best way to portray a character.

The Holiday (2006) – The Punch We All Cheered For

Although the purpose of the breakup scene in “The Holiday” is to help viewers empathize with Amanda, we can’t help but question whether the punch was necessary. She had already ended the relationship, and all she wanted was for him to acknowledge that he had been seeing someone else.

Source: Sony Pictures

She then punched him in the face. Twice. Not even in self-defense. Strangely, audiences seemed to cheer for her. This begs the question: What if the situation had been reversed? The reality of violence toward men shouldn’t be ignored, and many people today would not find that scene funny.