The early 2000s was a great time for comedy. It gave us unlikely heroes and outrageous spoofs and provided Hollywood stardom to comedic greats we all know and love, like Michael Cera, Seth Rogen, Jonah Hill, Bill Hader, and Ken Jeong.

And although it’s possible to achieve still gut-busting cinema with a pg-13 rating (uh, hello!? Talladega Nights!?), there’s just something about the raw, unfiltered jokes penned in r-rated comedies that really get the tears flowing. Take a trip down memory lane while we look at the best r-rated comedies that premiered before 2010 (sorry, Bridesmaids).

10. Scary Movie

Year Made: 2000

Scary Movie is brought to you by the zany minds of the Wayans Bros, who, by the early 2000s, had already secured their mantles as comedy kings of movie spoofs ( see examples: Don’t Be A Menace and I’m Gonna Git You Sucka). Scary Movie is not only one of the funniest movies from the early 2000s but also one of the most influential. After its 2000 premiere, you couldn’t call a friend without hearing “WAZZUP!?”.

Scary Movie put us on to the comedic talents of Anna Farris and Regina Hall, featured hilarious cameos from Carmen Elektra and Shannon Elizabeth, while also treating us to the hilarious dynamics of comedic vets like Cheri Oteri and, of course, Shawn and Marlon Wayans. This horror movie parody does a perfect job of poking fun at all the horror movie stereotypes we see in films like Scream, I Know What You Did Last Summer, and The Blair Witch Project while also tying in spoofs of some of the biggest blockbuster films at the time (like Charlie’s Angels, The Matrix, and American Pie).

9. The 40 Year Old Virgin

Year Made: 2005

The jokes from The 40 Year-Old Virgin never get old. It has a premise and an ensemble cast that still guarantee laughs to this day. The 40 Year Old Virgin was the first 2000s Judd Apatow comedy to kickstart Apatow’s “rat pack” era, in which he frequently cast comedians like Paul Rudd and Seth Rogen (as well as Jason Segel, Johan Hill, and Bill Hader).

The r-rated comedy in The 40 Year Old Virgin works so well thanks to the hilarious dynamics between the crude Seth Rogen, Paul Rudd, and Romany Malco and the seemingly innocent (and sexually oblivious) Steve Carrell. This romantic comedy is full of hysterical improvised scenes, such as the infamous waxing scene with Steve Carrell (which was actually done in real life) and a deleted scene with Romany Malco and Kevin Hart. Thanks to this rom-com and its amusing ensemble, I’ll never hear The Fifth Dimension’s Aquarius the same way ever again.

8. Shaun Of the Dead

Year Made: 2004

“You’ve got red on you.” Of course, Edgar Wright would find a way to make zombie movies funny. I expect nothing less from the mastermind behind Scott Pilgrim Vs. The World. I love Shaun of the Dead. Not only is it a spectacular comedy that put me on to the greatness of Queen’s Don’t Stop Me Now, but it’s also one of my favorite zombie movies thanks to its choice to make fun of an otherwise dramatic premise of a zombie apocalypse.

Don’t get me wrong, Shaun of the Dead certainly has some serious moments and will definitely tug at your heartstrings, but when there are jokes, they hit every time. And although Simon Peg, Dylan Moran, and Peter Serafinowicz delivered excellent on-screen performances, the real comedy grand prize goes to Nick Frost for his portrayal of the hilarious air-headed Ed, the best sidekick you could ever ask for in a zombie apocalypse. “Yeah, boyyyeee!”.

7. Harold & Kumar Go to White Castle

Harold & Kumar Go to White Castle is a movie whose premise is simple: two college friends get stoned and, thanks to a weirdly enticing television ad, decide they will stop at nothing to satisfy their craving for a meal from White Castle. What ensues from there is a nonstop, outrageously funny adventure with absurd twists, bizarre turns, and hilarious bits from Neil Patrick Harris.

Just when you think it can’t get any more insane, random, or funny, Harold & Kumar Go To White Castle takes you deeper into its rabbit hole. This movie not only made the world crave White Castle (no, really. The film reportedly drove sales up for the fast-food franchise), but it also made us all want to scream Wilson Phillips’ Hold On at the top of our lungs. Good luck getting past Kumar’s marijuana fantasy without losing your breath from laughter.

6. Superbad

Year Made: 2007

Ah, Superbad. The r-rated comedy that made us all love/hate the vulgar and obnoxious Jonah Hill. When this movie came out, it was the stuff of legends. People couldn’t stop going on about the awkwardness of Michael Cera, the obscenity of Jonah Hill, or the dorky, but somehow also, smoothness of your boy Christopher Mintz-Plasse aka McLovin.

Superbad is funny and extremely relatable, as we witness the coming of age story of two teenage pals who are desperate to make a name for themselves before they are forced to leave their friendship and their dorky high school personas behind. Superbad has protagonists you really want to see win while also giving us hilarious scenes that we can quote for days. The great lengths that Seth and Evan (who are named after writers Seth Rogen and Evan Goldberg) go to manifest their cool reputations is insane but guarantees roaring laughter every time. I’ll be damned if Seth Rogen and Bill Hader aren’t the coolest, most understanding crooked cops ever!

5. EuroTrip

If you read the title of this movie and instantly envisioned Matt Damon performing Scotty Doesn’t Know, you’ve come to the right place, my friend. This r-rated 2004 comedy is a riot. It depicts a tale of romance, friendship, growth, and determination while also poking fun at European caricatures such as the Red Light District, the USD exchange rate, and the passionate fandom of fútbol in the UK.

EuroTrip features hilarious cameos from David Hasselhoff, Lucy Lawless, and Fred Armisen as we follow the crazy backpacking shenanigans of Michelle Trachtenberg, Scott Mechlowicz, Jacob Pitts, and Travis Wester. Do yourself a favor and watch this early 2000s gem if you haven’t already.

4. Knocked Up

Year made: 2007

Knocked Up is another early 2000s r-rated comedy classic from the Apatow vault. It stars Seth Rogen in his first-ever leading role as unlikely hero Ben Stone who ends up in a co-parenting relationship with Katherine Heigl’s Allison Scott after the two hook up during a one-night stand.

Knocked Up is brilliant thanks to the misfit ensemble of Rogen, Jason Segel, Jonah Hill, and Jay Baruchel, as well as the awkward chemistry between Heigl and Rogen, who never seem to be on the same page about anything. As you watch the improbable twosome struggle to get to know each other, you can’t help but wonder: how the hell are these two going to raise a kid together? This rom-com features the first-ever movie role for Ken Jeong (who was actually a real-life doctor at the time) and the scene-stealing duet of Leslie Mann and Paul Rudd, who did such a fantastic job as the married couple, Debbie and Pete, that they eventually starred in their own spinoff (This Is 40.)

3. The Hangover

Year Made: 2009

The Hangover is good old-fashioned comedy gold and shows the magic that occurs when actors perfectly understand the assignment. The shocking twists, musical breaks, and legendary appearance from Mike Tyson sky rocked this r-rated comedy to record-breaking success, making it the highest-grossing r-rated comedy of 2009.

The Hangover is an amusing spin on a bachelor party gone awry after Stu (Ed Helms), Phil (Bradley Cooper), and clingy brother-in-law-to-be Alan (Zach Galifianakis) go through hell on high water to find their best bud and groom to be Doug (Justin Bartha) after a wild night of partying in Vegas. As the Wolf Pack retrace their steps through a series of various clues (including a tiger, an abandoned baby, and a butt naked Ken Jeong), all the things that could go wrong do so in the most hilarious way. Be on the lookout for the musical talents of Ed Helms, who improvises a hysterical tribute to his lost friend Doug on the piano.

2. Tropic Thunder

Year Made: 2008

Tropic Thunder is so good that we all just accepted the fact that Robert Downey Jr. wore blackface for most of it. Tropic Thunder hysterically pokes fun at Hollywood tropes and the complications of making a big-budget film; Ben Stiller plays the cheesy action star, Robert Downey Jr plays the intense character actor, and Jack Black is the goofy comic relief, and Brandon T Jackson plays the rapper attempting to crossover into acting. The premise alone is a knee-slapper: what would happen if four Hollywood actors were forced to portray action heroes in the real-life jungles of Southeast Asia while being completely oblivious to the fact that what they’re experiencing is real.

This early 2000s action-comedy has an A-list cast of comedy heavy-hitters like Steve Coogan, Danny McBride, and Matthew McConaughey. Look out for a cameo from action star Tom Cruise who is barely recognizable as the hot-headed Hollywood exec Les Grossman.

1. Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan

Year Made: 2006

Borat is another example of an early 2000s comedy with a huge pop culture impact; people everywhere could not stop talking like the reporter from the glorious nation of Kazakhstan (say it with me: Niiice!). The beauty of Borat is that most of the scenes are hidden camera pranks with real people who have no idea that Sacha Baron Cohen was in character the whole time. But c’mon, who doesn’t love a good prank!?

With all the obliviousness, cultural ignorance, and gender biases, this r-rated comedy stirred up a lot of controversies. Borat caused so much backlash that not only were the producers sued, but the police were called on Cohen over 90 times during production. Talk about a show-stopping performance.