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1. Twilight (2008)

When Twilight premiered in 2008, it became an instant sensation and sparked a cultural obsession with supernatural romance. However, while it left an undeniable mark on pop culture, this film has some major underlying issues.

Once viewed as swoon-worthy, Bella and Edward's relationship feels problematic in hindsight. He was controlling, exhibited stalker-like behavior, and gaslit her into believing that she imagined his supernatural abilities.

Add in the fact that Edward is technically over a century old when Bella is a high schooler, and it's clear why Twilight might not resonate with audiences the same way in 2025.

2. Knocked Up (2007)

Directed by Judd Apatow, Knocked Up was initially well-received despite heavily leaning on outdated gender stereotypes. The movie follows responsible and career-driven Alison, who is forced to navigate an unplanned pregnancy with slacker Ben.

Even though Knocked Up delivers plenty of laughs, it also portrays women, especially Alison, as rigid and joyless. Katherine Heigl, the lead actress, criticized this, too, saying the film "Paints the women as shrews, as humorless and uptight, and it paints the men as lovable, goofy, fun-loving guys."

3. Norbit (2007)

This movie might've showcased Eddie Murphy's ability to transform into multiple characters, yet Norbit is still more cringeworthy than comedic. The portrayal of Rasputia, an over-the-top and domineering woman whose character is built around fat-shaming jokes, is particularly offensive.

Moreover, Murphy also plays Mr. Wong, a wildly stereotypical caricature of an elderly Chinese man.

4. Shallow Hal (2001)

Shallow Hal may have set out to deliver a message about inner beauty, but it really missed the mark. Again, this film relies on fatphobic humor, with Gwyneth Paltrow's character serving as the target of the jokes.

It arguably reinforces stereotypes about weight and attractiveness, and Gwyneth (who wore a fat suit) actually called the movie a "disaster" in 2020.

5. White Chicks (2004)

Featuring over-the-top humor and absurd disguises, White Chicks was a hit in 2004. Nonetheless, it's a tired portrayal of women as materialistic, shallow, and obsessed with their looks.

The premise involves two FBI agents posing as socialites during a Hamptons weekend, and it was always meant to be ridiculous. Even so, there are certain scenes that are especially questionable, like when an athlete at the club attempts to spike a woman's drink.

6. Brüno (2009)

Brüno was intended to be a bold satire, Sacha Baron Cohen's specialty, but it crosses the line of edgy humor. He plays an exaggerated, flamboyant Austrian fashion journalist, and the mockumentary was meant to expose homophobia.

Despite that, the movie incorporated a lot of outdated gay stereotypes and might've reinforced the notions as opposed to challenging them. In fact, Gay and Lesbian Alliance Against Defamation (GLAAD) representative Rashad Robinson called the work "problematic in many places and outright offensive in others."

7. Wedding Crashers (2005)

Wedding Crashers revolves around two men who lie their way into weddings to manipulate women into sleeping with them. At its core, the film's plot is unsettling and questionable.

Aside from that, it features gay stereotypes, a racist grandmother, and scenes that blur the lines of consent. All that being said, t's obvious why this movie wouldn't fly today.

8. The Notebook (2003)

The Notebook is still one of the most favored romance movies of all time, so this may be an unpopular opinion, but some of its most iconic moments are more disturbing than anything.

There's no denying that Noah and Allie's love story is passionate, but his relentless pursuit of her is borderline manipulative. Remember when he threatened to let go of the Ferris wheel if she didn't go on a date with him?

Plus, once they actually get together, their relationship is filled with constant fighting, including scenes when Allie hits Noah. Female-on-male violence has traditionally been glossed over in films, but today, Hollywood is moving away from these problematic depictions.

9. How to Lose a Guy in 10 Days (2003)

This movie follows advice columnist Andie Anderson, played by Kate Hudson, who wants to write an attention-grabbing piece. She finds Ben Berry, an advertising executive who's arguably creepy and manipulative.

While How to Lose a Guy in 10 Days may be a classic rom-com, it relies on gender stereotypes that can feel more offensive than humorous now.

10. Mean Girls (2004)

Finally, we can't forget about Mean Girls, one of the most iconic teen comedies of the 2000s. Sure, it's filled with endlessly quotable lines and a sharp take on high school cliques, but it also has relentless body-shaming.

Many of the scenes would hit differently in today's more body-positive era, making Mean Girls a more cringey watch in 2025.