The 10 Best 2000s Comedy Movies, Ranked

The dawn of the new millennium was pretty solid when it came to big-budget comedy movies — so good, in fact, that winnowing this list down to just ten movies was actively difficult. Judd Apatow was making some of his best movies, including "Knocked Up," and the group known as the "Frat Pack" — a group that included Will Ferrell, both Luke and Owen Wilson, Ben Stiller, Vince Vaughn, and more — were releasing bangers like "Old School" and "Wedding Crashers" around this time. "Napoleon Dynamite" came out halfway through the 2000s and became an unexpectedly enormous hit to the point where every kid at your school started wearing a "Vote for Pedro" shirt. On the other side of the spectrum, unapologetically bawdy movies like "The Hangover" became overnight box office successes. Still, how can we narrow down the list of the best comedies of the 2000s to just ten movies? (For the purpose of this list, please ignore any creatively bankrupt sequels that followed these outstanding originals; the first movies are the only ones that matter.)

Somehow, we did it — so from a fish-out-of-water tale set at a beauty pageant to multiple Ferrell movies to some of the most quotable films in cinematic history, here are the ten best comedy movies that came out between 2000 and 2010, ranked from ... least incredible to most amazing. (None of these are bad, so it wouldn't be right to say ranked from "worst to best.") 

When tomboy turned FBI agent Gracie Hart — played by Sandra Bullock — is tasked with investigating a sinister plot involving a beauty pageant, she's not thrilled ... and her colleagues at the bureau take one look at her disheveled appearance and actively laugh at the idea of her competing in a beauty pageant. (It's almost ludicrous how far the movie goes to make Bullock, one of the most beautiful people on the planet, look ugly.) As Gracie Lou Freebush, who's representing the great state of New Jersey, the agent has to reach the final round of Miss United States to figure out who's threatening to bomb the event — and as it turns out, the call is coming from inside the house, so to speak.

With a supporting cast rounded out by incredible heavyweights like Benjamin Bratt, Michael Caine, Candice Bergen, and William Shatner, "Miss Congeniality" is way funnier and more charming than it has any right to be, and despite a romantic subplott with Bratt's character, Bullock gets to show off exactly how hilarious and charismatic she is without having to direct all of that energy at some guy. Plus, we get the immortal response from Heather Burns' Miss Rhode Island, Cheryl Frasier, when she's asked about her perfect date: "I'd have to say April 25th. Because it's not too hot, not too cold, all you need is a light jacket."

Judd Apatow's 2005 comedy "The 40-Year-Old Virgin" could have been an incredibly mean-spirited movie in the hands of a lesser director, but thanks to Apatow's careful direction and a sweet script he penned alongside star Steve Carell, the movie is unexpectedly heartfelt for a film that features a lengthy back-and-forth between two guys that repeats "You know how I know you're gay?" over and over again. Carell plays the titular virgin Andy Stitzer with such empathy and sensitivity that you never feel inclined to judge him while you're watching him admit his lack of experience to his friends — Seth Rogen's Cal, Romany Malco's Jay, and Paul Rudd's David — or as he flashes back to all of his near-misses (one notable one involves him accidentally kicking Carla Gallo in the face and breaking her nose). When Andy meets Trish Piedmont (Catherine Keener), he falls for her more or less instantly ... but obviously, admitting that he's never been intimate with anyone before is a major hurdle in their budding relationship.

With Jane Lynch, Kat Dennings, Elizabeth Banks, and Leslie Mann rounding out the supporting cast — as Andy's overly familiar boss, Trish's impetuous teenage daughter, and two women whom Andy pursues with disastrous results — "The 40-Year-Old Virgin" manages to balance its sillier, bawdier moments with real heart, thanks in large part to the performances and unabashedly honest script. Keep an eye out for Jonah Hill as a befuddled customer at Trish's store, who doesn't quite grasp the fact that he can't take a very unique pair of shoes home with him.

Let's pretend that "Zoolander 2" was never made and blissfully live in that alternate timeline — but despite that dreadful sequel's existence, the 2001 comedy "Zoolander" is still as funny as ever. Ben Stiller, who was on a serious winning streak at the time ("Meet the Parents" came out one year prior, and he also appeared in "The Royal Tenenbaums" in 2001), leads the film as dimwitted yet sweet male model Derek Zoolander, who agrees to star in a campaign for major fashion designer Jacobim Mugatu (Will Ferrell) without realizing that he's actually being primed to assassinate the Prime Minister of Malaysia. (Why? The official wants to crack down on sweatshop labor ... which would cause a serious problem for the fashion industry.) After Derek is brainwashed by Mugatu and his crew — including his henchwoman Katinka Ingabogovinana, played by a sneering Milla Jovovich — his new journalist ally Matilda Jeffries (Stiller's real-life wife Christine Taylor) and his former modeling nemesis Hansel (Owen Wilson) team up with the model to try and stop him from killing the Prime Minister during a runway appearance, and the whole thing is just as delightfully stupid as it sounds.

David Duchovny, Patton Oswalt, Jennifer Coolidge, Vince Vaughn, and Justin Theroux all show up at various points, alongside figures like Lenny Kravitz and Billy Zane playing themselves. For crying out loud, David Bowie plays himself in this movie, and future Emmy winner Alexander Skårsgard makes his film debut as one of Derek's modeling buddy. If you somehow haven't seen "Zoolander," all of this should convince you. Just know you'll never say the word "eulogy" correctly ever again.

It's pretty amazing that a lifelong screenwriting project by Seth Rogen and Evan Goldberg turned into one of the funniest teen movies ever made — and one of the very best comedies of the aughts. With Jonah Hill as Seth and Michael Cera as Evan, director Greg Mottola brings the two best friends through a truly wild night at the end of high school as the duo tries to impress cute girls, pick up alcohol using a fake ID (albeit one that bears the single name of "McLovin'" from the great state of Hawai'i), and get home safely ... without addressing the elephant in the room, which is that the lifelong besties are going to different colleges after graduation.

As Evan and Seth stumble through their genuinely insane evening — at one point, they go to a bizarre party and start pouring booze into laundry detergent bottles, at which point something absolutely unspeakable happens to Seth's shirt — their other friend Fogell (Christopher Mintz-Plasse), owner of the terrible fake ID, ends up on his own odyssey alongside two truly inept cops (played by Rogen himself and Bill Hader), shooting their guns and doing donuts in cop cars. Throw in the fact that this movie is Emma Stone's feature film debut — she plays Jules, the object of Seth's affection — and you've basically got a perfect comedy. That's without even mentioning that it's one of the most quotable movies ever ("Take off that vest, you look like Aladdin" is one of the only ones we can print here).

Speaking of quotable movies, you can't talk about unforgettable and incredible 2000s comedies without mentioning "Mean Girls." During the (first) peak of Lindsay Lohan's acting career, she joined Tina Fey's high school comedy as naive newcomer Cady Heron, whose family relocates from Africa to suburban Chicago. On her first day at North Shore High, Cady meets outcasts Janis Ian (an almost unrecognizable Lizzy Caplan) and Damian Leigh (Daniel Franzese), who help her make sense of the school's social structure — especially "the Plastics," the school's most popular girls led by the evil, shrewd queen bee Regina George (a ruthless and astounding Rachel McAdams). When Regina invites Cady to join her, Gretchen Weiners (Lacey Chabert), and Karen Smith (Amanda Seyfried) at their lunch table each day, Cady devises a plan with Janis and Damian to bring the school's ruler down once and for all ... until Cady ends up enjoying the power just a little too much.

Between "four for you, Glen Coco," "stop trying to make fetch happen," and "my breasts can always tell when it's raining," "Mean Girls" has some of the all-time funniest one-liners ever committed to film, and it certainly doesn't hurt that "Saturday Night Live" veterans Tina Fey, Amy Poehler, and Tim Meadows play the (equally dysfunctional) adults throughout the movie. "Mean Girls" is certainly popular — it spawned a musical, a movie musical, and even a holiday — which makes it easy to forget that it's also side-splittingly hilarious. (Ignore that movie musical, though.)

"Shaun of the Dead" stumbled slowly so that zombie comedies (zombedies?!) like "Zombieland" could run later on. Edgar Wright's comedy — which also serves as the first film in his "Cornetto trilogy" — stars frequent collaborators Simon Pegg and Nick Frost as disaffected best friends Shaun and Ed, who live unremarkable and frankly crappy lives in London ... until they're interrupted by a sudden zombie apocalypse. Shaun, who was dumped by his girlfriend Liz (Kate Ashfield) just before the first zombie appeared and has a tough relationship with his irascible stepfather Philip (Bill Nighy), goes about his life completely normally as the zombies emerge, only noticing there's any sort of issue when two appear in his backyard; from there, he and Ed set out to rescue Philip, Liz, and Shaun's mom Barbara (Penelope Wilson) and bring them all safely to his favorite pub The Winchester so they can at least wait out the whole situation with a pint in hand.

Sure, there aren't a ton of zombie comedies, but there's no question that "Shaun of the Dead" is the gold standard — and while "Hot Fuzz" and "The World's End" are also excellent, there are few things funnier in the entire world than the scene where a depressed Shaun heads out and buys some food without noticing swarms of the undead on the streets of London. Plus, we have to give credit to one of the best plot synopses in movie history, which goes like this: "We'll have a Bloody Mary first thing, have a bite at the King's Head, couple at the Little Princess, stagger back here, and then bang! Back at the bar for shots." (If you know, you know.)

When a movie opens with a breakup scene where the person getting dumped is fully naked, you know it's going to be pretty good — and that's definitely true of Jason Segel's 2008 comedy "Forgetting Sarah Marshall." Written by Segel himself and directed by Nicholas Stoller, the movie also stars Segel as Peter Bretter, who gets dumped by his TV star girlfriend Sarah Marshall while he's completely nude (an incident apparently taken directly from Segel's life). Heartbroken, Segel decides to take a trip to Hawai'i only to discover that Sarah and her odious new boyfriend, rock star Aldous Snow (Russell Brand), are also vacationing at his same resort ... and, point in fact, Sarah cheated on Peter with Aldous before she officially ended things. It's not looking good for Peter until he connects with Rachel Jansen (Mila Kunis), who works at the resort's front desk, and starts moving on.

Between the real details Segel threw into the script — specifically, the breakup and his original Dracula musical, which ends up becoming an integral plot point — and flat-out incredible performances from every single actor in the movie, "Forgetting Sarah Marshall" is both relatable to anyone who's ever suffered through a horrible breakup and one of the funniest comedies ever made. (The way Kunis screams "Dracula musical!!!!!" at the top of her lungs, offscreen and unseen, while Peter sits at a bar piano would achieve that feat even if the rest of the movie sucked, but it does not.) Segel's earnest and heartfelt performance anchors the whole thing, and best of all, it never got a sequel that would ruin the movie's legacy; it remains perfect just as it is.

Sorry, but there's no better way to describe the 2008 Will Ferrell-John C. Reilly movie "Step Brothers" better than Vulture did in their ranking of Ferrell's movies: "Not the most financially successful Ferrell comedy, but definitely the weirdest and most aggressively insane. This is a movie about lunatics made by lunatics, and there isn't a single scene that doesn't feel uniquely inspired and batsh*t nuts." That is spot-on, which is why "Step Brothers" is one of the dumbest, funniest, and best comedies of all time — not just the 2000s. Ferrell and Reilly go balls to the wall as overgrown children Brennan Duff and Dale Doback, whose parents Nancy Huff (Mary Steenburgen) and Dr. Robert Doback (Richard Jenkins) end up getting married and forcing the two bozos into close quarters; after beating the absolute crap out of each other, they "become best friends," build bunk beds (badly), and do karate in the garage. Unfortunately, their joint hijinks involving Robert's beloved boat end up driving Nancy and Robert apart, and the two separate as Brennan and Dale are forced into the real world. (This goes about as well as you'd expect in that they show up to a job interview together in matching tuxedos.)

"Step Brothers" truly is one of the strangest movies ever made. It's a movie where Kathryn Hahn seduces Reilly's Dale in a bathroom in a manner that's aggressive and borderline sinister and then props her leg up on a urinal to pee. It's a movie where Adam Scott leads his unwilling family in a car sing-a-long of Guns N' Roses' "'Sweet Child O' Mine" and berates them for hitting flat notes. It's a movie where Jenkins' Robert ends up confessing that he harbors a lifelong dream of ... being a dinosaur. (This is to say nothing of the Catalina wine mixer.) It doesn't matter how many times you've seen "Step Brothers" — it's always a truly deranged delight.

Reese Witherspoon won an Oscar in 2006 for her role as June Carter Cash in the Johnny Cash biopic "Walk the Line," but she should have won it for her hyper-specific, unbelievably committed turn as Elle Woods in the 2001 comedy "Legally Blonde." Directed by Robert Luketic, written by Karen McCullah Lutz and Kirsten Smith, and based on a book of the same name by Amanda Brown, "Legally Blonde" opens with Elle Woods and her girlfriends shopping for a perfect dress — because she thinks her boyfriend Warner Huntington III (Matthew Davis) is going to propose over dinner. When he dumps her instead because he's headed to Harvard Law School and needs to date somebody "serious" — as he puts it, "if I'm going to be a senator by the time I'm 30, I need to marry a Jackie, not a Marilyn" — Elle is heartbroken until she decides that she, too, will attend Harvard Law. Through sheer force of will and a ton of work, Elle gets accepted by the Ivy League institution — the scene where the committee watches her admissions video "directed by a Coppola" and figures out a way to admit her is an all-timer — and shocks Warner on their first day as "serious" law students. ("What, like it's hard?" she quips when Warner expresses his shock that she got in at all.) Unfortunately, Warner is engaged to the aristocratic Vivian Kensington (Selma Blair), and truthfully, Elle is a little underprepared for law school at first.

The beauty of "Legally Blonde" is that, by the end, it teaches you that you can succeed and wear pink and embrace your femininity if you so choose; you just have to access your inner intelligence and harness it. Alongside that heartwarming message, you've got Jennifer Coolidge bending and snapping, future horror director Oz Perkins playing an affable weirdo named David Kidney, and Linda Cardellini in a truly alarming wig as wealthy heiress Chutney Windham. "Legally Blonde" is a movie that can cheer you up on a day when you're down, and you'll also laugh the entire time.

It's impossible to rank the best comedies of the 2000s and not top the list with "Anchorman: The Legend of Ron Burgundy." Will Ferrell's all-time funniest comedy features the legendary funnyman as San Diego anchorman Ron Burgundy, who knows full well that he's beloved by the whole town — and on each and every broadcast, he's flanked by weatherman Brick Tamland (Steve Carell), field reporter Brian Fantana (Paul Rudd), and sports broadcaster Champ Kind (David Koechner). When the guys, led by the KVWN-4 director Ed Harken (the late, great Fred Willard), have to start working with the ambitious Veronica Corningstone (Christina Applegate), they all bristle at the fact that they have to cede airtime to a woman ... until Veronica and Ron start a relationship. 

Everything about "Anchorman" is freaking nuts, and it's perfect. Every moment of the movie is somehow memorable and iconic, from the news team battle royale to everything related to Ron's beloved dog Baxter to the fact that Brick never has any clue what's going on at any given moment. Sex Panther. "A glass case of emotion." Paul Rudd rocking a ridiculous mustache and screaming at a zoo panda. A major teleprompter mishap spurred by information from Kathryn Hahn's supporting character Helen. You can probably visualize all of these scenes just from reading that. "Anchorman" is one of the top five comedies ever made; of course it's the best of the 2000s.