20 Movies from the 2000s That Didn't Age Well

#20: “Transformers: Revenge of the Fallen” (2009)

Michael Bay’s robot sequel delivered the explosive action fans craved and dominated the box office in 2009. But strip away the still-awesome CGI, and you’re left with some glaring issues. Like Skids and Mudflap, who are probably the worst offenders. These two Autobots are painful racial caricatures, complete with exaggerated accents, gold teeth, and illiteracy jokes that wouldn’t even fly in the ‘80s. Add in the camera’s relentless, leering focus on Megan Fox, which treats her more like a hood ornament than a human being, and the whole thing feels sleazy. This movie was enormous back in the day, but the bottom-of-the-barrel humor, casual racism, and blatant sexism turn this chaotic blockbuster into a rather uncomfortable rewatch.

#19: “American Pie 2” (2001)

The “American Pie” franchise defined raunchy teen comedies for millennials, but hindsight ruins a lot of the fun. This summer-vacation sequel definitely amps up the gross-out gags, yet it frequently crosses the line from teenage hormones into outright creepy territory. Sure, the superglue scene is still iconic, but it’s completely overshadowed by some truly questionable material. Our protagonists become peeping Toms by watching women through windows, and the dialogue is heavily peppered with casual homophobia. The movie is also huge on the “Gay Panic” trope, with Jim and Stifler in particular being wildly uncomfortable with gay connotations. Add in the fact that the female characters have little agency and are mostly seen as objects to “win,” and you have a movie that has remained firmly stuck in 2001.

#18: “Good Luck Chuck” (2007)

Pitching a romcom where Dane Cook is a magical good luck charm for single women probably sounded like a fun, raunchy concept in 2007. But the reality is a pretty bleak watch today. The script treats its female characters solely as disposable stepping stones for the male lead to get what he wants. Worse, the runtime is absolutely stuffed with mean-spirited fat jokes, blatant objectification, and a serious sense of male entitlement regarding sex. Rather than coming across as a lovelorn guy trying to break a curse, Chuck just seems grossly manipulative. It’s less of a romantic comedy and more of a time capsule for mid 2000s misogyny that totally misses the mark today.

#17: “The Hot Chick” (2002)

A Rob Schneider comedy from 2002 hasn’t aged well? Well color us surprised. When a popular, mean-girl cheerleader magically wakes up in the body of a scruffy middle-aged man, the script relies purely on cheap panic for its punchlines. Almost every joke revolves around transphobia, homophobia, and aggressively punching down for an easy laugh. Rather than focusing on a fun lesson about walking a mile in someone else’s shoes, the narrative wallows in creepy situations and rampant sexism. What might have passed as a harmless low-brow comedy 25 years ago just feels mean-spirited to modern audiences.

#16: “White Chicks” (2004)

The Wayans brothers scored a massive hit with this comedy about two Black FBI agents going undercover as wealthy white sisters. Even though the movie has kept a passionate cult following and spawned a million memes, you really have to turn your brain off to ignore the problems here. The humor leans entirely on broad racial stereotypes, intense gender panic, and a frankly exhausting amount of fat shaming. Using terrifying prosthetics to mock another race and gender feels totally jarring in our current cultural landscape. Terry Crews singing Vanessa Carlton is still iconic, but the script’s heavy reliance on lazy tropes makes the rest of the runtime a pretty tough sit.

#15: “Me, Myself & Irene” (2000)

This Farrelly brothers road trip features a top tier Jim Carrey, but it totally faceplants when it comes to handling mental health. The story follows a mild-mannered state trooper whose suppressed rage manifests in a second personality. Unsurprisingly, the script uses a serious mental disorder strictly as a cheap vehicle for slapstick violence and outright cruelty. Beyond the blatant stigmatization of mental illness, the dialogue casually tosses around slurs and treats its female lead terribly. Audiences ate up the shock humor back in 2000, but watching it now just leaves a bad taste in your mouth. Turning a complex psychological condition into a tasteless punchline simply doesn’t hold up in an era where mental health is taken far more seriously.

#14: “Bride Wars” (2009)

Pitting Anne Hathaway and Kate Hudson against each other seemed like a guaranteed recipe for romcom gold. Unfortunately, this film thrives on the absolute worst stereotypes regarding female friendships. The entire plot hinges on the tired idea that women are so completely obsessed with getting married that they’ll transform into vindictive monsters if their dream day is threatened. Instead of communicating, these lifelong best friends engage in literal psychological warfare over a venue scheduling error. It aggressively pushes the toxic “bridezilla” trope to its breaking point, suggesting that a fancy party at the Plaza matters more than decades of loyalty. Rather than a breezy comedy, the whole movie just feels mean.

#13: “The Ugly Truth” (2009)

Romcoms usually thrive on the classic “opposites attract” dynamic, but “The Ugly Truth” is truly, well, ugly. The script tries to squeeze laughs out of a chauvinistic TV personality and the tightly-wound producer who supposedly needs his crude advice to find a man. The narrative bends over backwards to justify rampant workplace harassment, framing the guy’s overt misogyny as charming “tough love” that secretly hides a heart of gold. The idea that a successful woman needs to endure constant disrespect and completely change her personality to get a date is just all sorts of wrong. It strips this so-called romance of any genuine charm.

#12: “The Love Guru” (2008)

Mike Myers’ notorious flop was dragged by critics back in 2008, but time has highlighted how remarkably offensive it actually is. Myers tries to parody spiritual self-help gurus by playing an American raised in an Indian ashram. The result is a cringe-inducing collection of lazy stereotypes masquerading as comedy. The script leans painfully hard on juvenile bathroom gags, racial caricatures, and a grating mock accent that feels completely out of line. It doesn’t offer any clever satire; it just points and laughs at Eastern traditions without bothering to write a real joke. It proves that leaning on cheap cultural mockery does not a funny movie make. It really is no surprise that it ended Myers’s reign as a bankable leading man.

#11: “Boat Trip” (2002)

Cuba Gooding Jr. and Horatio Sanz star in this comedy about two straight men who accidentally book a vacation on a gay cruise. Critics rightfully trashed the movie at the time, but viewing it today is a genuinely jaw-dropping experience. The script relies entirely on a barrage of predatory gay stereotypes to generate its punchlines. Instead of clever misunderstandings, the humor only punches down, framing the LGBTQ+ community as either walking caricatures or aggressive threats. On top of the rampant homophobia, the movie throws in heavy doses of misogyny just to maximize the offensive factor. It’s a tasteless disaster that was already offensive in 2002. Today it’s just flat-out unwatchable.

#10: “Garden State” (2004)

When it was released, “Garden State” was a critical success, garnering comments from film writers like, “Not since "The Graduate" has a movie nailed the beautiful terror of standing on the brink of adulthood with such satisfying precision." That’s quite high praise. But as the years have worn on, and Natalie Portman’s character has come to exemplify the trope of the manic pixie dream girl, people have become less enamoured with this film that was once considered a cult classic. The movie is the opposite of subtle, beating you over the head with metaphors and “artsy” shots which, with some perspective, just look like a try-hard move.

#9: “Crash” (2004)

This movie may have won the Academy Award for Best Picture along with many other accolades, but even while it was being praised many questioned its quality. Now it is considered by some to be one of the worst movies of the decade. It attempts to tackle race but does so without any true perspective, redeeming a racist character when he clearly doesn’t deserve the audience’s sympathy. While it gets points for its diverse cast, it loses them quickly for its portrayal of racism in America. In retrospect, we really wish “Brokeback Mountain” had taken home the big award that year.

#8: “Knocked Up” (2007)

“Knocked Up” may have 90% on Rotten Tomatoes, which is quite a feat for a stoner romantic comedy, but in the decade since its release, it has lost a whole lot of fans. The plotline employs many tropes that were popular in the 2000s, like the uptight and straight laced woman who finds herself dating the loser dude. Even one of the film’s stars, Katherine Heigl, has called the movie sexist, saying that it "paints the women as shrews, as humorless and uptight, and it paints the men as lovable, goofy, fun-loving guys.”

#7: “Brüno” (2009)

We get it, “Bruno” is supposed to be satire, but even when something is created with a satirical edge, it can still end up being offensive. The film was criticized for leaning on gay stereotypes, and in the process perpetuating them, even if the intention behind the project was good. Rashad Robinson, a representative of the Gay and Lesbian Alliance Against Defamation (GLAAD) said that, “Sacha Baron Cohen's well-meaning attempt at satire is problematic in many places and outright offensive in others.” While we may have laughed at it when it hit theaters, it just doesn’t feel funny anymore.

#6: “I Now Pronounce You Chuck & Larry” (2007)

The simple concept of this 2007 movie seemed dated almost as soon as it was released. Two male firefighters decide to pretend to be gay and get married for insurance benefits, and you can basically imagine where the plot goes from there. On top of gay marriage being played as a funny plot device, this film also offers up some straight up misogyny as well. The Wall Street Journal deemed it offensive to pretty much everyone, calling it, “an insult to gays, straights, men, women, children, African-Americans, Asians, pastors, mailmen, insurance adjusters, firemen, doctors — and fans of show music." Whew!

#5: “Shallow Hal” (2001)

If you really look at the big picture, “Shallow Hal” is supposed to be about looking past appearances in order to really get to know people. But this movie manages to twist that general concept into something that is undeniably ugly, especially with a couple of decades of perspective. A man who generally focuses on appearances finds himself falling in love with an overweight woman - because his mind sees her as being thin and beautiful as he’s so taken with her personality. Throughout the rom-com, there is a ton of fat shaming and jokes based on women’s appearances, which definitely wouldn’t fly today.

#4: “The Notebook” (2003)

We love “The Notebook” as much as anyone else, but you can’t deny that in today’s social climate, many of the scenes would be considered more creepy than romantic. Sure, it’s considered one of the best romance movies of all time, and we agree that there are a lot of great parts, but the way that Noah pursues Allie at the beginning makes us cringe today. Of course, the stunt he pulls on the ferris wheel is weird and over the top, especially when he essentially threatens to kill himself if she won’t go out with him. But the follow-up conversation where he approaches her on the street really isn’t much better.

#3: “Love Actually” (2003)

Another beloved rom-com, another movie that sadly isn’t as well received today. These days, people aren’t nearly as wild about a plotline where the Prime Minister has a relationship with one of his staff members (especially the part where he tries to get her fired because he’s attracted to her). We once thought it was charming when Mark pursues his best friend’s wife and tells her he’s in love with her using poster boards, but now it seems like a crappy move. Not to mention all the fat jokes! We’re not saying you should cancel your annual viewing of this film when December rolls around, but maybe be a little more critical of how the characters act.

#2: “Avatar” (2009)

Considering it is one of the most successful films of all time, it should come as no surprise that there has been a certain amount of backlash when it comes to “Avatar”. It broke records upon its release and was praised for its visual effects, but a decade on the plot has some problematic elements to it. Not only have there been many accusations that the story told in “Avatar” was simply borrowed from other media (“Pocahontas” anyone?) but more importantly, it has been characterized as a “white savior” movie. This is because a native people need the help of the white man to save their society for them in the epic sci-fi flick.

#1: “Wedding Crashers” (2005)

Where do we even start with this one!? The basic premise of “Wedding Crashers” is troubling to begin with: two guys sneak into strangers’ weddings with the intention of lying to women in order to get them into bed. Throw in a racist grandmother, the trope that all gay men are predatory and some unconsensual physical intimacy and you’ve got an absolute mess of a movie that... unfortunately we all loved in 2005 when it was the highest grossing comedy of the year. Even one of the film’s stars, Isla Fisher, said, “I'm not sure that a Wedding Crashers sequel would work in the Time's Up movement.”

Do you agree, or do you think these movies still hold up? Let us know in the comments below!