The Top 20 Comedy Films of 2000-2009

The final list of my "Top 20 of the Decade" series belongs to none other than the comedy genre. Although the 2000's weren't as successful as the '70s or '80s when it came to churning out classic after comedy classic, there were still some memorable and even terrific films that made us laugh. Since I refuse to create a "Top 20 Dramas" list since there are WAY damn too many for one man to choose from, I also threw in some films that would be classified as comedy-dramas, or "dramedies".

20. Jackass Number Two (2006)

Have you ever been tempted to do something really, REALLY stupid/dangerous/crude? An act where you just knew good things wouldn't come of it, but your morbid senses of humor and spontaneity thought otherwise? Welcome to the world of Johnny Knoxville and his merry band of masochistic fools, where getting kicked in the nuts, skateboarding off of rooftops, chugging beer with your butt, acting as the bait for sharks, or drinking a horse's, uh, special fluid is the norm. The sequel of the successful 2002 reality comedy Jackass: The Movie (itself based on the wildly popular MTV series), Number Two amps the dangerous, crude, disgusting, and absolutely hilarious stunts to brand new heights. More polished and more professionally made than its predecessor (is "professional" the right word to use?), Number Two benefits from terrific, frathouse camaraderie between the risk-takers, not to mention doing what comedies SHOULD be doing: making you laugh, whether you're proud of yourself for doing it or not.

19. Superbad (2007)

By July of 2007, the Judd Apatow revolution was in full swing. After having gained critical and commercial acclaim with The 40-Year-Old Virgin and Knocked Up, Apatow began taking several burgeoning directors and screenwriters under his wing. One such screenwriter was Seth Rogen, a longtime collaborator of Apatow's who made his big on-screen splash in Virgin, and later gained the lead in Knocked Up. Considering their ample filmmaking chemistry, it only made sense for the two to collaborate on a screenplay by Rogen and his longtime comedy partner Evan Goldberg, called Superbad. Produced by Apatow and directed by sophomore director Greg Mottola, Superbad was a semi-autobiographical take on Rogen and Goldberg's teenage years. Seth (Jonah Hill) and Evan (Michael Cera) are two high school seniors and lifelong friends facing separation when Evan is accepted to Dartmouth. Invited to a party hosted by Seth's crush, Jules (Emma Stone), the duo plan on getting a lot of booze, and finally losing their virginity to their respective dream girls. A sweet, engaging, and VERY raunchy comedy, Superbad boasts a superb comedic rapport between Hill and Cera, with the entire show being stolen by newcomer Chris Mintz-Plasse as uber-nerd McLovin'.

18. Old School (2003)

College truly is a major transitional stage in one's life: it's a period where the fun of youth ends, and the responsibilities of adulthood begins. But what happens if, years after your hard-partying days, you feel the instinctual need to go back to that oh-so-sweet stage of drunken irresponsibility? That's the gist of Todd Phillips' anarchic Old School, a 21st-century homage to frathouse classics such as Animal House and Revenge of the Nerds. Thirtysomething friends Frank (Will Ferrell), Mitch (Luke Wilson), and Bernard (Vince Vaughn) are all at stressful moments in their lives: Frank just got married, Mitch moved out of his house when he caught his girlfriend cheating on him, and Bernard pretty much cannot stand his "family man" status. So when Mitch moves into a house near a college campus, the trio begin to return to their booze-filled glory days, much to the disdain of the college's Dean Pritchard (Jeremy Piven), who was teased mercilessly by the guys in high school. Old School gained cult popularity of its own, and was responsible for the post-"SNL" success of Ferrell, who's at his whacked-out best here. Ridiculous, vulgar, and riotously funny.

17. Hot Fuzz (2007)

After director/co-writer Edgar Wright and co-writer/star Simon Pegg brilliantly sent up the zombie genre with 2004's Shaun of the Dead, it was only natural that the British duo went after the next obvious choice of mocking-yet-loving satire: the shoot 'em up police movie. London police officer Nicholas Angel (Pegg) is the best cop in the business-- so good, in fact, that his fellow officers believe that he's making them look bad. As such, Angel is transferred to Sanford, a village virtually free of crime. Responding to even minor offenses like public drunkeness with overly dedicated professionalism, Angel is annoyed with his current situation, especially once he's partnered with a bumbling, overeager constable (Nick Frost). A sly, droll satire of Jerry Bruckheimer-style action flicks, Hot Fuzz delightfully mines every action movie cliche and convention, not to mention poking fun at British stereotypes. And once again, like in Shaun, the chemistry between Pegg and Frost is terrific, suggesting a modern-day Laurel and Hardy, with stiff English upper lips.

16. Rat Race (2001)

Since breaking out big with his brother David and friend Jim Abrahams with the classic spoof Airplane!, Jerry Zucker has been responsible for some great cult comedies, such as The Naked Gun and Kentucky Fried Movie. When the trio split to do solo work, Jerry returned to the zany comedy well and directed Rat Race, a wonderfully goofy ensemble film clearly gaining influence from the 1963 classic It's a Mad, Mad, Mad, Mad World. A random collection of people visiting a Las Vegas hotel/casino (including Breckin Meyer, Whoopi Goldberg, Rowan Atkinson, Seth Green, and Jon Lovitz) randomly discover special tokens, and are informed by the eccentric, gambling-happy billionaire Donald Sinclair (John Cleese) that a duffel bag containing $2 million is stored in a locker at a Silver City, NM train station. Each group given keys to open the locker, the race is on. A madcap comedy of errors, Rat Race benefits from a wide array of talented performers and silly, sight-gag-heavy Looney Tunes-style humor.

15. Pineapple Express (2008)

It's been a while since the "stoner comedy" genre churned out any memorable movies. In fact, not since the days of Up in Smoke and Fast Times at Ridgemont High have cannabis-themed films actually been truly funny. But in 2008, there was one surefire combination to bring back that comedy high: a producer in Judd Apatow, a deliriously funny script by Seth Rogen and Evan Goldberg, and guns. LOTS and LOTS of guns. And explosions. Arguably the first "stoner-action-comedy", Pineapple Express is a terrifically enjoyable satire of high-octane buddy action films, as well as a sweet return to "Cheech and Chong" style wackiness. Dale Denton (Rogen) is a process server and pot aficionado who witnesses a murder by crime lord Ted Jones (Gary Cole). Panicked, Dale drives off, accidentally leaving behind his roach of a rare breed of cannabis called "Pineapple Express", a strain which Jones easily traces back to Dale's dealer, Saul Silver (James Franco). Now Dale and Saul must go on the run, with gangsters and crooked cops on their tail. The mix of over-the-top violence and weed humor meshes well, and of course, Rogen delivers as usual, but kudos must go to Franco, whose zonked-out delivery and Spicoliesque cheerfulness is absolutely priceless.

14. The Hangover (2009)

Some would agree that a hangover is a sign of a great previous night. But MOST would agree that a hangover is the sign that you did some REALLY naughty things, and didn't even know about it. For groomsmen Stu (Ed Helms), Phil (Bradley Cooper), and Alan (Zach Galifianakis), it was more than just getting wasted and trashing their Vegas hotel room. There's also the fact that there's a tiger in their bathroom, Stu (a dentist) lost his tooth, a baby is found in a closet... oh yeah, and there's that small problem of the groom-to-be (Justin Bartha) nowhere to be found. If Old School was practice for director Todd Phillips, then The Hangover was perfection. A riotously funny comedy complemented by fabulous chemistry between the three leads (and a standout performance from Galifianakis), The Hangover turned out to be the sleeper hit of 2009, making $460 million worldwide on a $35 million budget, becoming the highest-grossing R-rated comedy ever in America.

13. Shaun of the Dead (2004)

Most zombies films focus on just that: the zombies. We're paying more attention to those ravenous undead monsters, rather than the one-dimensional victims they're going after. But what if we were to pay attention to the dramatic/romantic goings-on of the runaway zombie food? Mix a romance, a comedy with decidedly British humor, and bloodthirsty zombies, and you've got one of the funniest horror movies ever made. Directed by Edgar Wright (creator of the surreal British TV series "Spaced"), Shaun benefits from a fabulous send-up/homage to all things horror (especially the films of Romero), and hysterical lead performances by Simon Pegg and Nick Frost. A bloody good time.

12. School of Rock (2003)

I'm probably not the first to say that nowadays, there isn't as much focus as there should be on extracurricular programs at schools. Such afterschool activities have been known to help bolster students' creativity, skills, and chances for success beyond secondary education. But if you put Jack Black in charge of a class of fifth graders, chances are that the program will be given MUCH more attention, good or bad. A terrific and energetic home run from indie director Richard Linklater (Dazed and Confused, Before Sunrise), School of Rock is perfectly suited for Black's Tasmanian Devil-style energy. Dewey Finn (Black), a rock guitarist, is kicked out of his band for his massive ego and onstage antics. Threatened by his roommate's (Mike White) domineering girlfriend (Sarah Silverman) with eviction unless he gets a job, Dewey, in an act of desperation, impersonates his roommate and takes a substitute teacher job at a prestigious private school. Clearly the most unprofessional teacher there is, Dewey nonetheless realizes that his class of fifth graders are musically talented, and decides to assign them a special project: becoming the next big rock band. A delightful, very funny romp, where Black's antics are highly entertaining rather than obnoxious.

11. Ocean's Eleven (2001)

You can't find many genres that are more fun than the caper film. Famous for plot twists, infectious senses of humor, and ensemble casts, the genre never disappoints when it comes to pure entertainment. Such is the case for Steven Soderbergh's Ocean's Eleven, a spirited, ridiculously fun remake of the 1960 Rat Pack film of the same name. Recently paroled con artist Danny Ocean (George Clooney) violates his parole by traveling to California, where he meets up with his old heist partner Rusty Ryan (Brad Pitt) and plans the biggest job ever: robbing three Las Vegas casinos owned by Terry Benedict, Ocean's old rival. Getting their old crew back together, Ocean and Ryan stack the deck against Benedict, and prepare for the biggest heist of the century. Cleverly written and directed, Ocean's Eleven would be nothing without its excellent ensemble cast, a veritable who's who of Hollywood heartthrobs and legends (including Matt Damon, Don Cheadle, Casey Affleck, Bernie Mac, Carl Reiner, and Elliot Gould). Light, fast-paced, and fabulously entertaining.

10. Elf (2003)

As I've stated before, Will Ferrell's spastic man-child works only in certain kinds of situations. And usually, it doesn't work. Luckily, director Jon Favreau was able to harness Ferrell's unique brand of comedy perfectly in Elf, a terrifically enjoyable Christmas comedy. Over thirty years ago, Santa Claus (Ed Asner) visited an orphanage on Christmas Eve, not noticing an infant crawling into his toy bag. Upon returning to the North Pole, Santa discovers the baby, and decides to have the child, named Buddy, raised by Papa Elf (Bob Newhart) as one of the elves in Santa's Workshop. Flashforward to present day: Buddy (Ferrell) is frustrated by the fact that he's the only elf that's over six feet tall, and is unable to make toys as proficiently as he should. Then comes the horrifying news: Buddy is a human, and his biological father (James Caan) is on Santa's naughty list. Therefore, Buddy decides to venture into the real world, unprepared for the not-so-jolly world of New York City. This is Ferrell's show, through and through. Absolutely hilarious in his childlike performance, it's a hoot just to see him in a green and yellow elf costume.

9. In Bruges (2008)

Despite what you may think, not ALL gangsters and hitmen are completely lacking in morals or decency. Some of them may have a heart of gold underneath their dangerous, trigger-happy exteriors. Some may even experience guilt from certain actions, even if it comes with the job territory. In Martin McDonagh's black comedy In Bruges, that old "emotionless killer" stereotype is broken down, in a wonderfully dark way. Hiding out in the Belgian city of Bruges, Irish hitmen Ray (Colin Farrell) and Ken (Brendan Gleeson) are awaiting instruction from their boss, Harry (Ralph Fiennes). Despite his snarky and antisocial personality, Ray holds a dark secret that's wracked him with guilt. But when Harry orders Ken to kill Ray, loyalties and friendships are put to the test. A very dark and bleak morality tale, In Bruges benefits from a wicked sense of humor, as well as terrific performances from all three leads.

8. The 40-Year-Old Virgin (2005)

Sex is always a touchy issue to discuss. Even tougher to disclose is whether or not you've even REACHED home base... especially if you're middle-aged. Andy Stitzer (Steve Carell) managed to go forty years without doing the deed, and he's gotten by pretty well. He's a stockroom worker at an electronics store, maintains a comfortable routine, and he's a pretty nice guy. He's also a nerd with a massive action figure collection, and he rides his bike everywhere. So after inadvertently spilling his secret to his wild co-workers (Paul Rudd, Romany Falco, and Seth Rogen), they egg Andy on to set out to finally lose his virginity. The first directorial feature by Hollywood powerhouse Judd Apatow, Virgin is a terrific example of how decidedly raunchy material can mesh with three-dimensional characters and an underlying sense of sweetness. Carell delivers a charming, highly likable performance, and the supporting cast of Rudd, Malco, and Rogen steal the show wherever they go.

7. Team America: World Police (2004)

Even though it's the most powerful nation on the planet, America hasn't always had the best relationship with the rest of the world. Many accuse the U.S. of imperialism, fostering a very unilateral foreign policy, and overall arrogance. And on the home front, liberals and conservatives are always at each other's throats. So who's better to capitalize on the comedic potential of such contentious issues than Trey Parker and Matt Stone? The creators of the hugely popular "South Park" franchise, Parker and Stone have always been equal-opportunity offenders. So with Team America: World Police, the duo waste no time tearing apart sacred cows. Utilizing cheesy marionette puppets (think "Thunderbirds"), Jerry Bruckheimer- and Michael Bay-style action cliches, and a LOT of vulgar humor, Team America earned its place as a comedy classic. A story about a team of American commandos hunting down terrorists (usually with ultra-destructive results), Team America takes potshots at both Republicans and Democrats, and does so with aplomb. It also has the funniest puppet portrayal of North Korean dictator Kim Jong Il ever, and one of the most insanely funny sex scenes caught on celluloid. A must see.

6. Sideways (2004)

Wine's never been a favorite of mine. I've never truly understood the whole "culture" revolving about the beverage, as well as the wine "etiquette" amongst the more hardcore wine drinkers (such as the "correct" way to drink wine, or traveling to wineries). But Miles Raymond (Paul Giamatti) is one such person, and just remember, he HATES Merlot. Miles and his best friend Jack Cole (Thomas Haden Church), a commercial actor, travel to Santa Ynez Valley wine country a week before the latter's wedding (mostly so Jack can sow his wild oats one and have a fling one last time). What follows is a moving, intellectual, and very funny exploration into middle-age, lost relationships, and the ability to start over, with terrific performances by Giamatti, Church, and Virginia Madsen.

5. Knocked Up (2007)

Just like his previous The 40-Year-Old Virgin tackled losing one's virginity, Judd Apatow now covered yet another very special landmark revolving around the dirty deed: pregnancy. Continuing his streak of raunchy-yet-sweet comedies that made him a household name, Apatow brings us Knocked Up, a hysterically funny, unapologetically vulgar, and surprisingly emotional comedy. Slacker Ben Stone (Apatow protege Seth Rogen) and up-and-coming television personality Alison Scott (Katherine Heigl) meet at a bar, get drunk, and have a one night stand. Going their separate ways the next morning, Alison finds out eight weeks later that she has more than her career to worry about. Informing Ben of her pregnancy, the two prepare to become parents, all while awkwardly attempting to forge a relationship. Like Virgin, Knocked Up has a vulgar, sophomoric face, but underneath, it possesses a likable, human, and emotional core. Ben and Alison's situation is portrayed realistically, and their shaky chemistry is treated with genuine sentiment rather than one-dimensionality.

4. Best in Show (2000)

Every Thanksgiving, I indulge in the guilty pleasure of viewing the National Dog Show. I just find it fascinating how these people primp and baby their canines to utter (almost obsessive) perfection, as if winning this contest would validate their place in the world. In Christopher Guest's hysterical mockumentary Best in Show, we're given a backstage look into the madcap world of dog breeders and handlers. Sure, it's a fictional story, but one wouldn't be exaggerating too much to say that this isn't like the real thing. Guest's second foray into the mockumentary genre (following 1997's Waiting for Guffman), Best in Show benefits from a terrific cast left to their own performer's instincts, since most of the film's dialogue is largely improvised. All cast members a top-notch, especially Eugene Levy, John Michael Higgins, Parker Posey, and Fred Willard.

3. Burn After Reading (2008)

A major motif in most of the Coen Brothers' movies is the stupidity of humanity in general. No matter what your standing in society is, odds are that you have a li'l bit of stupid in ya. Fargo was a great example (of course, being set in Minnesota means you don't have to look too far for the less-than-sharp), as was The Ladykillers. After winning three Oscars for their somber, dark offering No Country for Old Men, the Coens returned to their lighter fare with Burn After Reading, an uproarious comedy of errors where everything seems to be connected, but in the end, it just doesn't make sense. After caustic CIA analyst Osbourne Cox (John Malkovich) quits his job, he decides to write his memoirs. His wife (Tilda Swinton) decides to file for divorce, and downloads many of his personal and financial files from his computer. By accident, the disc containing those files end up at a fitness club, where employees Chad (Brad Pitt) and Linda (Frances McDormand) assume the files are highly confidential, and plan to blackmail Cox for a hefty ransom. From start to finish, Burn After Reading is a madcap, paranoid, deliciously dark Looney Tunes cartoon trapped in a spy caper. The cast is fantastic (especially Pitt as a gloriously dimwitted personal trainer, and George Clooney as an adulterous and paranoid Treasury agent), and the Coens have a blast showing just how dumb we as a species are able to be.

2. Little Miss Sunshine (2006)

Nobody's perfect. Everyone has flaws, be they big or small. But is that necessarily a bad thing? Eight-year-old Olive Hoover (Abigail Breslin) isn't the most glamorous little girl, but she still doesn't relent in her dream of beauty pageant glory. Too bad her incredibly dysfunctional family doesn't help matters. Little Miss Sunshine is a fantastic, irresistible celebration of the unconventional and the underdog. In Albuquerque, a very unordinary family is headed by Richard Hoover (Greg Kinnear), an unsuccessful motivational speaker with a huge Type-A personality. His wife Sheryl (Toni Collette) struggles to maintain her sanity as a mother of two; teenage Dwayne (Paul Dano), Sheryl's son and Richard's stepson, is a Nietzsche-reading brooder who took a vow of silence; Sheryl's brother Frank (Steve Carell), a gay Proustian scholar, has moved in after a failed suicide attempt; Richard's foul-mouthed, heroin addict father Edwin (Alan Arkin) has also moved in after being kicked out of his retirement home; and the couple's sweet, energetic daughter Olive. When Olive is accepted to compete in a California beauty pageant, the family takes an 800-mile road trip in their VW Bus, all while trying to sort out their differences. A charming, moving, and delightful masterpiece, Sunshine is a terrific study of family dynamics, self-esteem, one's place in the world, and the joy of just being yourself. Boosted by a stellar cast (especially Collette, Carell, and Breslin), Sunshine is a definite winner in any category.

1. Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan (2006)

It's understandable why other countries occasionally view Americans with contempt. After all, not all of the citizens of the United States are the most sophisticated, tolerant, or selfless. Of course, it's easy to stereotype, especially when it comes to scripted, fictional films. So what if the film in question featured REAL Americans, rather than actors portraying wildly stereotypical characters? British comedian Sacha Baron Cohen does just that, with his groundbreaking "mockumentary" comedy Borat. Based on a character from his terrific HBO series "Da Ali G Show", Borat explores those corners of America that usually aren't easily captured on camera. Kazakh journalist Borat Sagdiyev (Cohen) leaves his beloved home of Kazakhstan, followed by his portly producer Azamat (Ken Davitan), to travel to America for a supposed documentary chronicling American culture. Borat goes on to interview a wide array of Americans, from uptight feminists and Southern sophisticates, to jingoistic rodeo fans and drunken frat boys. But here's the kicker: the people Cohen (as Borat) encounters are real people, unaware that the casually racist, sexist, and anti-semitic Borat isn't the real deal. What follows is a fascinating, shocking, and uproariously funny look at America, bigotry, and how the two aren't always exclusive of each other. Cohen pulls off a marvelous task, remaining in character while interacting with truly colorful people (as well as when it comes to nude wrestling matches), and his Borat is a priceless comic creation. A terrific exercise in comedic perfection, Borat ranks as the greatest comedy of the last decade.


And now the Top Five WORST Comedy Films of the Decade:
5. Mr. Deeds (2002)

A classic 1936 Gary Cooper comedy reworked as a shallow, unbelievably stupid Adam Sandler comedy? Sheesh, is NOTHING sacred? Sandler plays a small-town pizzeria owner named Longfellow Deeds, who finds out that he's the heir to a $40 billion fortune. Wacky, scatological mayhem ensues. Same old Sandler manchild persona with just a different name and movie title.

4. Gigli (2003)

Hey, remember these two? Oh, 2003, what good times you gave us. You started with the boring and dull Hulk, went to the atrociously bad Dumb and Dumberer, assaulted us with From Justin to Kelly (but thankfully only in theaters for six weeks), and finally, you delivered the coup de grace with Gigli, the nadir of Ben Affleck's career, the unfortunate host to a foul (and sadly unforgettable) oral sex joke from Jennifer Lopez, and overall one of the worst stains on the underwear of popular culture. Basically a means of promoting the "Bennifer" hype, Gigli became one of the worst flops of all time (only recouping $7 million of its $54 million budget). "Gobble, gobble", indeed.

3. Talladega Nights: The Ballad of Ricky Bobby (2006)

Now I know some of my friends are going to hate me for this, but come on. Will Ferrell's idiot manchild persona works best in only the most controlled of situations, and this farce was not one of them. It would have been a brilliant "Saturday Night Live" sketch, but this annoying tale of a hotshot NASCAR driver bloated its one-joke premise to an ungodly 108 minutes. Not even Sacha Baron Cohen playing a gay French Formula One racer couldn't save this piece of crap.

2. The Hottie and the Nottie (2008)

I'll be honest: I never saw this movie. I don't WANT to see this movie. You couldn't PAY me to see this movie. But really, when you see the trailer for this film, you watch all you really need to watch. I'm not even going to bother describing the plot of this vain, stupid, offensive crime against humanity. All it does is keep professional whore Paris Hilton in the spotlight, no matter how negative that spotlight is. And the worst thing about this film? Hilton plays the "hottie". Are you fucking kidding me? I'd go for that wart-ridden, toad-faced "nottie" any day of the week.

1. Disaster Movie (2008)

The title says it all. Basically, the movie is a series of poorly-structured vignettes parodying movies released in theaters mere months (or weeks) before. Therefore, Disaster Movie got its "material" from its targets' theatrical trailers. This is essentially the lowest point of the "parody movie" genre. Once it was great, what with classics like Airplane, Hot Shots, and The Naked Gun. But after the second Scary Movie, the well ran dry, giving us monstrosities like Date Movie, Epic Movie, Superhero Movie, Meet the Spartans, and now this piece of penguin shit. Awful, awful, awful.