Judd Apatow's directorial debut The 40-Year-Old Virgin changed the film comedy landscape. Apatow and his co-writer and star Steve Carell set out to make a raunchy R-rated comedy that was far smarter, sweeter, and more emotionally resonant than anyone would be expecting from a movie called The 40-Year-Old Virgin.

The movie's groundbreaking use of improvisation led to a new record for the most footage used for a feature-length film. Carell became an A-list star overnight in the lead role, while Seth Rogen and Paul Rudd's movie careers were similarly kickstarted by the movie. So, here are the 10 funniest scenes in The 40-Year-Old Virgin.

10 Speed Dating

In order to get Andy into the dating game, the guys take him speed dating. As one would expect, Andy's attempts to flirt are hilariously terrible, and he meets one woman whose breast falls out of her shirt. He subtly adjusts his own shirt in an awkward attempt to get her to do the same. Meanwhile, David bumps into his ex Amy, whom he's been hung up on for years, played by Mindy Kaling early in her career.

9 Nicky Drives Andy Home

Andy's first shot at getting laid arrives when he and the guys start talking to a bachelorette party at a bar and Andy hits it off with Nicky, played by Leslie Mann. She tries to drive him home, but they don't end up getting there as she crashes the car a couple of times and throws up all over him.

8 David Watches The Bourne Identity

When Matt Damon starred as an amnesiac secret agent in The Bourne Identity, he quickly shed his image as an emotional dramatic actor and showed moviegoers he could kick butt.

Among those moviegoers was David in The 40-Year-Old Virgin, who watched the movie at the tech store where he works and said, "You know, I always thought that Matt Damon was like a Streisand, but I think he's rockin' the sh*t in this one!"

7 The Cast Sings "Aquarius/Let The Sunshine In"

In the final scenes of The 40-Year-Old Virgin, Andy marries Trish and finally loses his virginity. In order to convey what he's feeling, Andy starts singing the 5th Dimension's two-song medley "Aquarius/Let the Sunshine In" to the camera.

The musical number spills out into the field where the wedding took place as all the major cast members from the film join in.

6 Jonah Hill Tries To Buy Go-Go Boots In Trish's Store

Trish owns a store, but she doesn't sell anything in the store; people bring their stuff in and she sells it on eBay for them. It's very confusing — as Andy points out, she doesn't really need the store.

Most confused of all is a customer played by Jonah Hill (pushing his way into the Apatowian company of actors by stealing one scene as an unnamed character), who wants to buy some go-go boots and can't understand why Trish won't let him buy them.

5 "You Know How I Know You're Gay?"

If this gag appeared in a movie today, it definitely wouldn't fly. And to be fair, it is inherently homophobic. But in The 40-Year-Old Virgin, it works to convey how immature and out of touch Cal and David are. They sit around Andy's apartment, playing video games, and calling each other gay. They repeatedly use the phrase "You know how I know you're gay?" and come out with seemingly ad-libbed barbs.

4 Andy Covers For Jay

When Jay's girlfriend finds his card from the speed dating that he and the guys took Andy to, he asks Andy to cover for him and say that it was his card. Jay's girlfriend asks Andy to justify using some of the misogynistic language on the card and Andy affects a persona that really doesn't suit him. Steve Carell perfectly delivers milquetoast Andy's attempts to sound cool.

3 David Hates Michael McDonald

At the tech store where the guys work, there's a Michael McDonald concert DVD playing around the clock. Having listened to it all day every day for months, David finally gets sick of it.

He tells his boss Paula, played brilliantly by Jane Lynch, "If I have to hear 'Yah Mo B There' one more time, I'm gonna 'Yah Mo' burn this place to the ground."

2 Bag Of Sand

The guys first find out that Andy's a virgin when they invite him to their after-work poker game and start sharing sex stories. When they ask Andy to share one, he makes up a story about a girlfriend he had and says, "You know, when you grab a woman's breast...and you feel it, and...it feels like a bag of sand."

1 The Chest-Waxing Scene

Easily the funniest and most memorable scene in The 40-Year-Old Virgin sees Andy's friends accompanying him to get his chest hair waxed off. Steve Carell actually got his chest waxed for the scene, and all the dialogue is improvised.

The beauty parlor employee doing the waxing is laughing at Carell for real, and his angry reactions to her laughter are totally ad-libbed — as is the guys' commentary.

NEXT: Bridesmaids' 10 Funniest Scenes

Next Spider-Man: 10 Memes That Perfectly Sum Up The Sam Raimi Movies

About The Author

Ben Sherlock (3628 Articles Published)

Ben Sherlock is a writer, comedian, independent filmmaker, and Burt Reynolds enthusiast. He writes lists for Screen Rant and features and reviews for Game Rant. He's currently in pre-production on his first feature (and has been for a while, because filmmaking is expensive). You can catch him performing standup at odd pubs around the UK that will give him stage time. Previously, he wrote for Taste of Cinema, Comic Book Resources, and BabbleTop.

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