
It’s easy to criticize movies from the 1970s and 1980s for being outdated, but these 2000s movies haven’t aged well either.
John Tucker Must Die (2006)

This movie is absolutely a product of its time. Beneath a thinly veiled attempt at criticizing womanizer character John Tucker, the movie really serves more to glamorize him and make him out to be cool for dating so many women at the same time.
I understand that the movie is supposed to be about women teaming up together to defeat a common enemy, which is nice, but there is wayyyy too much sexualization of high school aged girls in this movie.
However, it does barely squeak past the Bechdel test, which is requires three things to pass: 1. It has to have two (named) female characters who 2. talk to each other 3. about something other than a man.
I Now Pronounce You Chuck and Larry (2007)

Whew — where to begin? We all love Adam Sandler, but this movie has a lot of elements that would never be accepted today.
To name a few, two straight men pretending to be gay in order to abuse the system is problematic for obvious reasons, and the countless gay jokes aren’t funny anymore by today’s standards; Rob Schneider in yellow face; Sandler’s character acting predatory towards Jessica Biel’s character, who trusts him because she thinks he’s gay, when in reality, he’s ogling her.
Waiting… (2005)

Let’s start with this line: “Hey there Natasha, how’s my favorite minor doing today?” Ryan Reynolds’ character asks a hostess. “I’m only a minor for another week,” she says.
Let that give you a taste of the sexism, homophobia, and misogyny in this movie. While it has its funny moments that many who have worked in the restaurant industry will find relatable, there are a shocking amount of jokes and scenes about sexual harassing women at work, pursuing minors sexually, and using foul words like the F slur that we won’t repeat here.
This 2000s movie has not aged well at all.
What Women Want (2000)

This movie isn’t as outright problematic as some others on this list, but it still has some very outdated ideas about women.
The plot revolves around Mel Gisbon’s character, a suave and successful man who magically gets the power to hear women’s thoughts. He soon realizes that virtually all the women in his life can see right through him, and don’t find him as charming as he thinks he is. However, there are some lame bits, like the scene in which the entire joke just the fact that Mel Gibson is wearing pantyhose. Now that gender fluidity and dressing in drag is much more accepted in society, these parts fall flat.
Gibson’s character is also way too easily forgiven by the women in his life, including by his daughter, who views him as an absentee father until he shows up to her prom one single time to help her, as if that makes him some kind of hero.
The 40 Year-Old Virgin (2005)

This movie is beloved by many, but watching it again, you might notice that a lot of the jokes have not aged well. Revolving around Steve Carrell’s character Andy, who has never had sex at the age of 40, the film revolves around his friend’s attempts to help him lose his virginity.
There are jokes about women not being able to drive, a lot of slut-shaming remarks, and even a problematic scene where Catherine Keener’s character Trish gets angry when Steve Carrell’s character Andy refuses to have sex with her. Yes, we know, it’s a comedy classic — but there are a lot of parts that just aren’t as funny as they used to be.
Bring It On (2000)

It only takes about 10 seconds of watching just the trailer for this movie to see that it’s all about sexualizing teenagers. It also uses the R-slur and a big plot point about white cheerleaders stealing Black cheerleaders’ work.
Though it’s considered a classic teen movie, you could never have a scene today with a high school cheerleader going topless at a football game and call it comedy.
The Hangover (2009)

Another comedy classic that has some scenes that are really uncool today. Perhaps the worst is the scene that revolves around Ed Helms’ character being disgusted when he finds out that the sex worker he had a relationship with is actually a trans woman.
Helms and Bradley Cooper’s characters make a big show of being grossed out when the realize that Yasmin Lee’s character Kimmy is actually a trans woman. Now, this scene is really hard to watch.
Wedding Crashers (2005)

Much of the plot of Wedding Crashers revolves around the main characters lying to and deceiving women in order to sleep with them. There’s a racist grandmother, sex that is not consensual, and jokes about gay men being predators.
Even Isla Fisher, who has a role in the movie as a virgin who becomes obsessed with Vince Vaughn’s character after they sleep together (also unfunny), told the Herald Sun: “‘I’m not sure that a Wedding Crashers sequel would work in the Time’s Up movement.”
Crash (2004)

One could argue that this one never aged well to begin with, but it did win the best picture Oscar over Broke Back Mountain. It’s since been criticized for its shallow take on racial issues.
The main complaint is that Crash presents the idea that racism can be cured and absolves white characters of their horrible past too easily, like Matt Dillon’s police officer character who assaults Thandiwe Newton’s character but is forgiven later because he saves her from a burning car.
There’s also the scene when Sandra Bullock’s racist character is seemingly absolved because she falls down a flight of stairs, and also decides to be nice to a Latina maid — as if that makes all the problematic things she did before somehow okay.
Knocked Up (2007)

The plot of Knocked Up follows Seth Rogen as a loser-type who sleeps with Katherine Heigl’s hard-working TV journalist character. When she gets pregnant, they decide to try to stay together and be co-parents.
But Heigl doesn’t feel that the film was fair to women. She notably said in a 2008 Vanity Fair interview that she found the film “a little bit sexist” because it “paints the women as shrews, as humorless and uptight, and it paints the men as lovable, goofy, fun-loving guys.”
She also said “it exaggerated the characters, and I had a hard time with it, on some days. I’m playing such a bitch; why is she being such a killjoy?”
Her co-star Seth Rogen and director Judd Apatow seem to disagree, however. Rogen told The Hollywood Reporter in 2016 that he felt “betrayed” by her comments, and director Judd Apatow said in 2009 on Howard Stern that he expected to get an apology from Heigl that never came.
Shallow Hal (2001)

This movie is one giant fat joke, and it’s been widely criticized for that, including by star Gwyneth Paltrow, who wore a fat suit for it. She called acting in the film a “disaster,” and its easy to see why when you consider the plot of this film. Jack Black’s character Hal is put under a spell that allows him to see only women’s “inner beauty”, causing conventionally attractive but mean-hearted women to appear fat but kindhearted women to appear thin, and therefore, by this movie’s standards, beautiful.
That carries with it the mistaken implication that thinness goes hand in hand with good qualities like kindness, while fatness is synonymous with bad qualities. Hal starts dating Paltrow’s character, Rosemary, who is, in reality, fat, but who appears thin only to him.
Further fat-shaming in the film includes but is not limited to: a scene when Jason Alexander’s character tries to “rescue” Hal from speaking to fat women at a club; referring to Rosemary as a “rhino”; a scene in which Rosemary jumps into a pool causes a splash so large that it cast a small child into a tree. We rest our case.
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Main image: Bring It On. Universal Pictures