These shameless 2000s comedies tried to outdo each other in terms of outrageousness. It was a different time.

Not Another Teen Movie (2000)

Credit: C/O

One of our favorites 2000s comedies is a pitch-perfect sendup of ’80s and ’90s comedies: Not Another Teen Movie is brutal takedown of teen movies from Lucas to She’s All That to Fast Times at Ridgemont High to The Breakfast Club, but it’s obvious its creators love teen movies and really know their stuff.

There’s lots of sex and violence and racial humor, yes, but it’s almost always in service of making fun of the sex and violence and racism of ’80s teen movies. The one shockingly violent joke — which ends with a pipsqueak bisected football player declaring “I’m a hero!” Is one we think about often. And we love the cameos from the likes of Mr. T and Molly Ringwald.

Not Another Teen Movie could cut every offensive joke and still be very funny, but it gets extra points for the sheer audacity of keeping them in.

White Chicks (2004)

Credit: Columbia

Marlon and Shawn Wayans play Black FBI agents who impersonate rich white socialites to infiltrate a pompous Hamptons social scene — and break up a conspiracy.

Yeah, it’s a broad setup. But the movie fully seizes on its funny premise when the duo learn how white people act when they think no one of other races are around — and start to see the world from a woman’s perspective.

If you’re not offended by something in White Chicks, you aren’t paying attention. The Wayans take down privileged white people, sure, but they also make some sharp observations about weird racial and sexual hangups, leaving no one unscathed.

It’s one of those 2000s comedies that has aged better than anyone expected, a few jokes aside.

America: World Police (2004)

Credit: Paramount

It’s hard to say who or what this comedy hates the most: xenophobia, Kim Jong-Il, or Matt Damon.

The creators of South Park missed at the box office with this one, but they were right and audiences were wrong.

It’s a masterpiece of smart-dumb moviemaking, especially a scene in which a drunk explains U.S. foreign policy with a disgusting metaphor about three body parts.

And the musical numbers are absolutely top-notch. This is one of our favorite 2000s comedies and one of the most ridiculously audacious comedies ever made.

Borat (2006)

Credit: 20th Century Fox

By far the best movie on this list — and there are a lot of great 2000s comedies — Borat is the story of sexist, anti-Semitic, generally clueless Kazakh journalist whose idiocy puts everyday Americans at ease enough to say some truly horrible things.

Sacha Baron Cohen’s unbelievably good, mostly improvised acting makes you laugh, but also lament the open prejudice he encounters. His feigned guilelessness brings out the worst in people, and makes us wonder how we would behave in their shoes.

Somehow we end up feeling sorry for Borat, but even sorrier for the state of things. The 2020 sequel, Borat Subsequent Moviefilm, is also terrific.

Tropic Thunder (2008)

Credit: Paramount

Tropic Thunder viciously and hilariously lampoons Hollywood self-importance at every turn, but especially with Ben Stiller’s Simple Jack character and Robert Downey Jr.’s portrayal of Kirk Lazarus, an Australian actor who really, really commits to playing a Black character.

Though some people have accused the movie of insensitivity, Stiller has admirably stuck to his guns.

“I make no apologies for Tropic Thunder,” Stiller tweeted when someone erroneously said he had apologized for the film. “Don’t know who told you that. It’s always been a controversial movie since when we opened. Proud of it and the work everyone did on it.”

John Tucker Must Die (2006)

20th Century Studios – Credit: C/O

John Tucker Must Die criticizes the womanizing ways of its lead character (Jesse Metcalfe) while also making him look… pretty cool.

It also offers a female empowerment narrative — a bunch of girls John Tucker has wronged team up to enact revenge — while simultaneously sexualizing its young characters in a way that was very typical of Maxim-era 2000s comedies. A classic case of Hollywood having it both ways.

Here’s how little the John Tucker team cares if you’re offended about their movie aging badly: A generation later, they’re working on a sequel.

Wedding Crashers (2005)

New Line Cinema – Credit: C/O

The Wedding Crashers revolves around the main characters (Vince Vaughn and Owen Wilson) deceiving women in order to sleep with them. There’s also a bit about a gay son who is basically a sexual predator.

Sure, the guys get their comeuppance and learn to change their scamming ways. But we’re still asked to root for them — what a couple of scoundrels! — until the turnaround.

As star Isla Fischer told the Herald Sun: “‘I’m not sure that a Wedding Crashers sequel would work in the Time’s Up movement.”

Knocked Up (2007)

Universal Pictures – Credit: C/O

Knocked Up, one of the biggest hits of all 2000s comedies, follows Seth Rogen as a fairly unmotivated guy whose hookup with a Type A TV journalist (Katherine Heigl) leads to an unexpected pregnancy. They opt to try to make it as parents.

There are crass jokes all over the place, but that’s not the issue. Heigl 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,” while the men are “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 b—-; why is she being such a killjoy?”

Rogen told The Hollywood Reporter in 2016 that he felt “betrayed” by her comments, and writer-director Judd Apatow said in 2009 on Howard Stern that he expected to get an apology from Heigl that never came.

Shallow Hal (2001)

20th Century Studios – Credit: C/O

Shallow Hal is a big fat joke that even one of its stars, Gwyneth Paltrow, has criticized in retrospect. It’s about a man named Hal (Jack Black) who falls under a spell that causes him to only see a woman’s inner beauty.

As a result, many conventionally attractive but cruel women appear fat, while the kindly but heavyset Rosemary (Paltrow in a fat suit) appears lithe and flawless. The internal logic of the movie is that skinny is better.

It’s also easy to be offended at the notion that larger women would throw themselves at the average and shallow Hal if only he would pay them the slightest bit of attention. It turns up often on lists of 2000s comedies that didn’t age well.

Brüno (2009)

Universal Studios

With same-sex issue a big and divisive issue in the 2004 presidential campaign — and its long-overdue 2015 legalization very much on the horizon — the 2000s were a very big decade for jokes about gay panic.

Sacha Baron Cohen’s Borat followup sets out to lampoon homophobia the same way Borat mocked xenophobia — he plays a charater who is so silly and lacking self-aware that the unsuspecting real people he entraps feel free to let down their guard and say incredibly ignorant things.

But Brüno is such an exaggerated and stereotypical character — as well as an inconsiderate buffoon, sexuality aside — that’s it’s easy to understand why he often freaks people out. Are they always offended by his being gay? Or perhaps by his frequent rude-at-best attempts to cross their boundaries?

Which isn’t to say Brüno isn’t funny. Every once in a while he finds the perfect target and executes his points perfectly. We think often of the ridiculous self-defense scene and the showstopping line, “How do you defend yourself against the man with two d—–s?

I Now Pronounce You Chuck and Larry (2007)

Universal Pictures – Credit: C/O

The whole point of Chuck and Larry is to dance around dicey issues, and it delivers.

Released before the aforementioned 2015 Supreme Court decision that made same-sex marriage the law nationwide, it’s the story of two New York firefighters, Chuck (Adam Sandler) and Larry (Kevin James) who pretend to be gay so that Larry’s children can be beneficiaries of his life insurance policy. (Just go with it.)

Things get tricky when Chuck falls for their lawyer, Alex (Jessica Biel) and gains her trust under the falsehood that he’s gay. And the gay panic jokes galore — were ubiquitous and risque in 2000s comedies — just seem dated now.

Liked This List of Shameless 2000s Comedies That Just Don’t Care If You’re Offended?

20th Century Studios – Credit: C/O

You might also like 12 Poppin’ 2000s Movies Only Cool Kids Remember or this list of Shameless ’90s Comedies That Don’t Care If You’re Offended.

Main image: I Now Pronounce You Chuck and Larry. Universal Pictures.