The 40-Year-Old-Virgin is an ode to early 2000s humor. On August 11th 2025, this movie will be turning 20 years old, and to say it started Judd Apatow’s career off with a bang (literally) is an understatement. This being his debut directorial film shows just how raunchy humor can get you far in this industry.

1.

Trish: What is this, your roofie, your date drug?
Andy: It’s a Mentos. They’re the fresh-maker.

2.

Andy: You know the thing about relationships is that they make one person go, “Blah blah blah blah blah,” and the other person go, “What are you talking about?” And then one person goes, “Blah blah blah blah blah.”

Cal: How much have you had to drink, man?

Andy Stitzer: Oh, how much have I had to drink? Hey, how many pots have you smoken?

Cal: What are you talking about?

Andy: Oh, how many times have you gone to the bathroom in your life? Let me ask you that. You know what, you don’t have an answer for that, do you? Who the fuck you, man? I’m sorry. No, no, no, no, you’re such a good guy, and I appreciate you.

3.

Mooj: Hey Andy, don’t let him bother you. It’s okay not to have sex. Not eveybody’s a pussy magnet. You, uh, what are you, 25?

Andy: I’m 40.

Mooj: Holy shit, man, you got to get on that!

4.

David: [to a shirtless Andy, who has an incredibly hairy chest] I love your sweater. Does that come in a V-neck?

5.

Andy: You know what? I respect women! I love women! I respect them so much that I completely stay away from them!

6.

Mooj: Tell me something, when your child is born, is he already on parole?

7.

Haziz: Today’s forecast? Dark and cloudy, and chance of drive-by.

8.

Paula: I’ll probably re-watch “Gandhi”.
Cal: “Gandhi” baked is good. I always feel bad when I watch it baked because I get really hungry and I’m eating a lot and poor Gandhi is starving his ass off.

9.

Andy: I hope you have a big trunk… because I’m puttin’ my bike in it.

10.

Nicky: You have really kind eyes, you know that?
Andy: Thanks. Umm… your hat has sequins.