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Readers’ Poll: The 10 Funniest Movies of the 2000s

‘Superbad,’ ‘Old School’ and your other selections

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Courtesy of Columbia Pictures

Many great comedies aren't fully appreciated when they first hit theaters. Movies now widely considered classics like Step Brothers and Anchorman were initially released to mixed reviews, while other films like Walk Hard or Wet Hot American Summer were greeted with outright hostility. Thankfully, time has a way of rescuing these movies, and cults sometime form around even the most unlikely box office disasters. After our recent celebration of Step Brothers, we asked our readers to vote on their favorite movies of the 2000s. Click through to see the results. 

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10. ‘The 40-Year-Old Virgin’

It's hard to imagine how different the world of comedy would be today had The 40-Year-Old Virgin never been created. Not only was it a breakthrough film for Judd Apatow, it also turned Steve Carrell into a huge star. Before the movie came out, he was merely seen as the former Daily Show correspondent that had just struggled through a shaky first season of The Office. After it exploded, the show's producers learned how to present Steve Carrell's character as a more sympathetic figure, and the second season of The Office was absolutely stellar. There would be no Parks and Recreation or Community had that not happened. The movie was also a launching pad for Seth Rogen and Jonah Hill, two of the biggest stars in Hollywood today. 

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9. ‘Walk Hard: The Story of Dewey Cox’

Without any doubt, John C. Reilly is one of the funniest people in Hollywood. He more than holds his own against Will Ferrell in Step Brothers and truly deserves to be a leading man, but this box office disaster threw that plan wildly off course. Here, he plays a dim-witted rock star that seems to go through every single phase of music history during the past few decades, and it's absolutely hysterical. Sadly, rock-themed movies rarely do well, and this never found an audience. It grossed just $18 million domestic and a pitiful $2 million overseas. Its failure pushed Reilly back into supporting roles in films like Terri and Cedar Rapids. He continues to work regularly, but we hope the day will come soon when he gets leading roles in big comedies. If that movie is Step Brothers 2, all the better. 

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8. ‘Shaun of the Dead’

Zombie movies are often deadly serious. Look at World War Z and 28 Days Later: They manage to tell the tale of reanimated corpses threatening the very existence of mankind with a completely straight face. The genius of Shaun of the Dead is that it knows the very idea of zombies is patently ridiculous, so it plays the whole thing for laughs. Simon Pegg plays a bored retail employee who finds himself in the unlikely position of battling a zombie revolution, all the while trying to impress his girlfriend. It grossed just $30 million worldwide but has become a cult classic. 

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7. ‘Napoleon Dynamite’

Back in 2004, almost nobody saw Napoleon Dynamite coming. After all, it was the first full-length effort by Jared and Jerusha Hess, a married Mormon couple in their mid-twenties who were almost completely unknown in Hollywood. The only person with any sort of fame in the cast was Haylie Duff, and the plot centered around a highly bizarre high schooler that befriends a quiet kid named Pedro and helps him run for class president. Many early reviews were mixed, but the movie somehow caught on with audiences and slowly became a sensation, grossing $46.1 million on a $400,000 budget. Unfortunately, the Hess' and and star Jon Heder were unable to follow it up with anything nearly as successful, even their ill-fated 2010 Napoleon Dynamite cartoon series. 

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6. ‘The Hangover’

After two disappointing sequels, it's a little easy to forget just how brilliant the original Hangover was back in 2009. One of the biggest hits of the year, it instantly transformed Zach Galifianakis into a comedy icon and made Bradley Cooper one of Hollywood's top leading men. It's the story of three guys that wake up after a particularly insane night in Las Vegas and realize they've lost their friend on the eve of his wedding. They remember nothing from the evening and are forced to re-trace their steps through Las Vegas. It grossed $467 million and generated two follow-up movies that used the Karate Kid, Oceans 11 and Super Mario Brothers approach to sequels: take the second one to a faraway land and bring the third one back to the site of the original. It rarely works, though Super Mario Brothers 3 is absolutely brilliant and perfect. The same cannot be said for The Hangover 3. It was so bad that even President Obama made fun of it when he was interviewed by Zach Galifianakis on Between Two Ferns

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5. ‘Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan’

Even Sacha Baron Cohen will likely admit that the whole Borat thing got a little out of hand in the fall of 2006. Everywhere you went you heard random people screaming out quotes from the movie. Meanwhile, stories about the real-life people in the movie dominated the news, as did stories about the stunned reaction by the actual residents of Kazakhstan, many of whom were unhappy about being portrayed as a group of backwards, anti-semitic, prostitute-crazed, potassium-exporting, Uzbek-slaughtering monsters. Audiences in America had a different reaction and the film grossed $128 million. It also raised expectations for Cohen's next few movies, and he's never quite matched the success or acclaim of Borat

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4. ‘Step Brothers’

Step Brothers arrived in theaters at a time when Will Ferrell was in a bit of a slump. His recent movies Stranger Than Fiction, Blades of Glory and Semi-Pro all failed to find a real audience, so when something brilliant like Step Brothers came it didn't receive a fair hearing. Many critics were brutal, and Roger Ebert gave it a scant 1.5 stars. "[It] has a premise that might have produced a good time at the movies," he wrote, "but when I left, I felt a little unclean." The film grossed $100 million and was deemed a moderate success, but as the years went by and TBS began airing it over and over it started to take on a new life. It holds up remarkably well to repeat viewings, rivaling only the original Anchorman for the title of the greatest Will Ferrell movie. A sequel seems increasingly unlikely, but we remain hopeful. 

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3. ‘Old School’

The premise of Old School is very simple: A group of dissatisfied guys in their thirties try to re-live their college glory days by starting their own fraternity. They recruit a motley crew of frat brothers varying wildly in age and do battle with college administrators while becoming campus legends. The casting was brilliant, down to Craig Kilborn as a smarmy douche. It was outgrossed in its first week by Daredevil, but it's hard to imagine a single person on planet earth who stills preferrs that movie to Old School. It's an overstatement to say it's become Animal House for a new generation, but not a huge one. (By the way, where has Luke Wilson gone? Why did they stop putting him in movies?)

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2. ‘Anchorman: The Legend of Ron Burgundy’

The enormous publicity push behind Anchorman 2: The Legend Continues turned off some fans of the original movie. All of a sudden, the hero of their beloved cult movie was everywhere. He was mixing it up with morning show hosts in character, taking over real-life newscasts and smiling down on enormous billboards all over the country. This was hard to imagine in 2004. The movie was a hit, but it didn't cross the $100 million threshold and reviews were rather mixed. Like many movies on this list, however, it took a few viewings before people really understood its the bizarre brilliance. It built and built for years until a sequel became inevitable. Needless to say, the sequel didn't quite capture the magic of the first one. A big part of comedy is surprise, and people pretty much knew what was coming.

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1. ‘Superbad’

Seth Rogen and his writing partner Evan Goldberg wrote the first draft of Superbad when they were teenagers, but by the time they got enough Hollywood pull to make the thing, they were way too old to play its stars. Instead, they turned to Jonah Hill and Michael Cera and even cast a teenage Emma Stone as one of the love interests. The story of two virgins trying to get laid during one crazy evening is quite old, but it has never been this funny or insane. The film grossed $170 million on a $20 million budget and created some huge movie stars along the way. Nobody at the time could have imagined that Jonah Hill would wind up nominated for multiple Academy Awards, but Hollywood is a weird place and he's a supremely talented guy. 

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