The turn of the millennium brought with it many new things. Bold fashion choices, a golden era in music, and some of the best comedy films ever made. While some R-rated comedies in the 2000s that changed the genre for years to come. Although not every joke lands quite in the same way all these years later, there are still so many films that hold up upon multiple rewatches.

With career-launching performances from the likes of Jason Segel, Seth Rogen, and Michael Cera, many of the 2000s' best rom-coms and comedy movies featured huge stars of the future. Established actors like Reese Witherspoon and Sandra Bullock also made some of their most iconic films, which have been revisited time and time again. Many of the films grossed well over $100 million at the box office, despite being made on lower budgets, getting some awards recognition as well. Then there are the underrated gems that might have gone under the wire, but are certainly worth seeing.

10 Not Another Teen Movie (2001)

Directed by Joel Gallen

Spoof movies had been a huge trend in Hollywood for many years. Films like Airplane and Robin Hood: Men in Tights would take a well-known film, often multiple films, and mimic its plot in a comedic way. Some scenes would be recreated nearly shot for shot, but instead of being taken seriously, they'd be played for laughs. While this trend seems to have died down lately, the 2000s were rife with such projects, and Not Another Teen Movie kicked it off for a new millennium.

From a hilarious line delivery in the style based on Bring it On, which was a huge hit, to a slow-motion hallway scene a la the criminally underrated Jawbreaker, no film was safe from ridicule.

With the huge popularity of teen films at the time, it made sense that they should get the spoof treatment. It starred Chyler Leigh and pre-Marvel Chris Evans, in a plot mostly based on She's All That, but the references to many well-known teen movies were plentiful. From a hilarious line delivery in the style based on Bring it On, which was a huge hit, to a slow-motion hallway scene a la the criminally underrated Jawbreaker, no film was safe from ridicule. For better or worse, it reignited the trend that spawned Vampires Suck and Scary Movie, but this stab at the genre is still fun to watch to see just how many references they were able to get in.

9 Pineapple Express (2008)

Directed by David Gordon Green

Bringing together a cast that is friends in real life usually translates incredibly well to the screen, with a lot of the jokes and comedy coming from a place of familiarity. This is evident in Pineapple Express, as the actors all bounce off each other in a natural and inviting way. Produced by the extremely prolific Judd Apatow, this action comedy blends jokes with a fast-paced adventure centered around a group of people who enjoy partaking in recreational drug use. A popular theme of the time, it had a very particular target audience in mind.

Lending into raunchy jokes and a lot of poking fun at other characters, the movie has become a cult classic filled with zingy one-liners. Seth Rogen, who was often typecast in the 2000s as a loveable loser, plays this part to perfection, assisted by James Franco and Gary Cole. It's a great snapshot of the millennial generation and its sense of humor. The movie made over $100 million at the box office and has a score of 68% on Rotten Tomatoes.

8 The 40-Year-Old Virgin

Directed by Judd Apatow

Apatow's first huge feature film hit was also a breakout role for Steve Carell. He had already secured his iconic role as Michael Scott in The Office, but this movie made him a box office draw as well. He brought his excellent comedic timing and natural charm as a sweet but shy salesperson who has little to no experience with women and intimacy of any kind. Aided by a brilliant ing cast that included many of the director's frequent collaborators, such as Seth Rogen and Paul Rudd, he begins his journey into dating to a huge comedic effect.

There are so many moments that are still side-splittingly funny, like the waxing scene and Jonah Hill's many attempts to shop at a store that only sells things on eBay, but it still managed to have a lot of heart. Catherine Keener is brilliant as the love interest and, despite the goofy nature of the movie, it manages to have some genuine romance in it as well. It grossed $100 million at the American box office alone, and remains one of the most quoted films in Carrel's filmography. With 85% on Rotten Tomatoes, it proves that it was as popular with critics as it is with audiences.

7 Juno (2007)

Directed by Jason Reitman

Written by Diablo Cody, Juno took advantage of the explosion of indie teen comedies in the 2000s. The titular character showcased her wit and sharp tongue in the best way possible. Following the story of a pregnant teen, it touches upon some very serious topics but always with a tongue-in-cheek attitude. A breakout role for Elliot Page, it includes a stellar ing cast including Jennifer Garner, Allison Janney, and J.K Simmons. Michael Cera's outfit choice was one of the most recreated Halloween costumes, and his performance stole the hearts of many viewers around the world.

The script is one of the stars of the movie, earning an Academy Award for Cody, as well as three further Oscar nominations.

The film also managed to make over $230 million on a budget of just around $7 million, which proved that indie films can find worldwide success. Its Rotten Tomatoes score is 93% and being referenced in a popular 2024 Sabrina Carpenter song shows that it continues to find new audiences in a whole new generation.

6 I Love You, Man (2009)

Directed by John Hamburg

A twist on the classic romantic comedy genre, this film is all about friendship. Paul Rudd's character realizes he doesn't have any notable male friendships to speak of as he gets engaged, and with his wedding party seemingly non-existent, he decides to start going on "friend dates". It was a clever idea that is relatable to this day, especially with technology taking away a lot of human , so even after nearly two decades, there is a lot to connect with. The movie also relies on the undeniable chemistry between the two leads, as they seem to be enjoying themselves as much on screen as the audiences are while watching.

The stellar ing cast includes the likes of JK Simmons, Rashida Jones, and Andy Samberg, and even sees a cameo from the band Rush. Jason Segel is very funny as the chaotic and eccentric Sydney Fife who helps Peter come out of his shell. There is a hilarious runner about Lou Ferrigno, aka The Hulk, and so many one-liners from Rudd as the slightly awkward lead as he attempts banter. "See you later Jobin" is one of the funniest lines of the movie, which still stands the test of time. Its 82% score on Rotten Tomatoes is testament to that.

5 Miss Congeniality (2000)

Directed by Donald Petrie

This undercover police comedy reinvigorated Sandra Bullock's career as one of her best movies for the new decade and was a huge box office smash worldwide. While she had already proved she had some good comedic timing in various rom-coms in the '90s, Miss Congeniality cemented that while increasing her bankability as a movie star. While the idea that she may in any way be deemed unattractive was a very 2000s trope, her performance as a slightly uncouth and awkward agent is what makes it truly believable. While very much a comedy, it's also packed with action and an intriguing mystery as well.

The makeover sequence is still very funny, showcasing how much work goes into taking care of one's appearance.

Michael Caine and Candace Bergen bring their legend status to the mix, and all the beauty pageant contestants have their very own moments to shine. The makeover sequence is still very funny, showcasing how much work goes into taking care of one's appearance. Fish out of water stories are very relatable, which is what makes the movie endearing as well as entertaining. It grossed over $200 million worldwide and has had a lasting legacy, as well as its very own sequel.

4 Anchorman: The Legend of Ron Burgundy (2004)

Directed by Adam McKay

Will Ferrell's career thrived in the 2000s, with huge hits such as Elf and Step Brothers, and his portrayal of Ron Burgundy shows just how great his comedic skills are. In one of the most memorable roles, he made a pompous and arrogant news anchor into a beloved character. While the stakes may not seem particularly high, audiences are taken in by Ferrell's on-screen presence and the great ing cast. With scene-stealing turns from Steve Carell and Paul Rudd, the film is packed with comedic talent.

The newsreader street fight scene, jazz flute solo, and milk drinking disaster are a trio of comedy delights, adding an absurd twist to this classic of the genre. It was hugely influential and made Ferrell the go-to for comedy roles of the time. From the costume styling to the quotable script, Anchorman is the gift that keeps on giving. Its sequel brought back many of the popular characters and shined a light on a host of new comedic talent as well.

3 Forgetting Sarah Marshall (2008)

Directed by Nicholas Stoller

Part of a popular trend of the time, of creating romantic comedies that appealed to wider audiences, Forgetting Sarah Marshall fused laughs with a heartwarming story that resonated with a wide variety of viewers. As Peter (Jason Segel) navigates a brutal split, he finds himself on vacation at the same resort as his ex and her new boyfriend. The breakup scene alone, is worth seeing, as the fully nude Segel receives the devastating news in the most vulnerable state imaginable.

Another highlight is his performance of a song from the Dracula musical that his character created, which never fails to amuse. The ing cast reads like a who's who of comedy greats, including Paul Rudd, Jonah Hill, and Kristen Wiig, who make their small parts some of the most memorable of the whole film. The Hawaiian setting is extremely pleasing to the eye, and Mila Kunis and Kristen Bell bring a lot of charm to the screen. A big success, the movie made over $100 million and has a score of 82% on Rotten Tomatoes.

2 Legally Blonde (2001)

Directed by Robert Luketic

Elle Woods is an inspirational character who proves that if someone sets their mind on something, they too can achieve it with hard work and determination. Playing with the trope of a ditzy sorority sister with a penchant for pink and tiny dogs, Reese Witherspoon adds so much depth and charm to a character who tends to be underestimated and sidelined. Imagining a fashion student attending Harvard Law School may seem funny in itself, but there's a lot more to the story than meets the eye.

The film is all about empowerment and believing in oneself, while still making viewers laugh along the way. The message transcends time, and it's no wonder that this beloved character is being brought back to the screen in a highly anticipated prequel. A standout performance from Jennifer Coolidge cements the film's status as one of the seminal comedies of the decade. It made nearly $150 million worldwide and features one of the best courtroom scenes in cinema history.

1 Little Miss Sunshine (2006)

Directed by Jonathan Dayton and Valerie Faris

Some comedies rely on big, broad jokes, outlandish concepts and ridiculous sequences created to make audiences laugh. But, Little Miss Sunshine subverts this formula, with even the big dance number being more about a heartfelt family moment than just a comedic trope. The cast features many actors who weren't even widely known for comedy, including Toni Colette, Alan Arkin, and Greg Kinnear, but it's their chemistry and the clever writing that make the film work so well. Abigail Breslin's breakout role is the glue that holds the narrative together, and she does it with the utmost charm.

The plot follows a unique little girl whose ambition is to take part in a beauty pageant, despite not conforming to the typical characteristics one would expect. She enjoys eating ice cream, and foregoes the grueling work ethic that the scene is known for. But the real story happens en route to the event, with the family bonding and working through their issues along the way. There are moments when viewers laugh through their tears, and that's what makes it so special. The movie won two Oscars, and has a score of 91% on Rotten Tomatoes.