- Ollie: [to Gertie] You're the only thing I was ever good at.
- Gertie: Thank you, daddy.
- Ollie: Anything for you, Gert. You know why?
- Gertie: Why?
- Ollie: Because you're the only thing I was ever really good at.
- Teacher: Everyone, please take your seats. You heard the bell. You know what it means. Last week, the assignment was to write an essay about your family. Who they...
- Teacher: [class: "Are!"] And what they...
- Teacher: [class: "Mean to us!"] Excellent droning.
- Gertie: I hate you! I hate you! I wish you died, not MOMMY!
- Ollie: I hate you right back, you little shit! You and your mom took my life away from me. I just want it back!
- Bart: Sun even shines on a dog's ass some days.
- Greenie: You getting a dog?
- Maya: That was kind of sweet. I'm kind of crushing on you right now, Trinkle.
- Ollie: "Cats" is the second worst thing that ever happened in New York City.
[after talking to Gertie, after finding her with Brian without their pants on]
- Ollie: Do you have any questions about what you saw?
- Gertie: [thinking hard] Do you have what Brian has?
- Ollie: Yes.
- Gertie: [after thinking hard again] Is it as big as his?
- Ollie: Sadly, yes.
- Ollie: George Michael is all about the ladies. "I want your sex". Does that sound like he's singing to a guy?
- Boy #5: Okay, it's like this. My dog ate my paper. I checked, but he didn't poop it out.
- Bart: Try acting like a father, shit-head.
- Gertrude: [very pregnant Gertrude is getting ready for the VMAs] You try getting ready quickly when you look like this! I'm so fat and there's going to be nothing but beautiful skinny girls there!
- Ollie: That's because they're all coked-out whores, honey.
- Gertrude: [now crying] I want to be a coked-out whore!
- Ollie: They're just skinny because they're coked-out whores.
- Gertrude: [sobbing] I want to be a coked-out whore!
- Ollie: Okay, you can be a coked-out whore. You can be a coked-out, coked-out whore.
- Maya: I do it at least twice a day.
- Ollie: Good God!
- Ben Affleck as Oliver "Ollie" Trinké
- Liv Tyler as Maya
- Raquel Castro as Gertie Trinké
- George Carlin as Bart Trinké
- Jennifer Lopez as Gertude Steiney
- Stephen Root as Greenie
- Mike Starr as Block
- Jason Biggs as Arthur Brickman
- Will Smith as Himself (uncredited)
- Jason Lee as PR Exec. 1
- Matt Damon as PR Exec. 2
- Paulie Litt as Bryan (as Paulie Litowsky)
- Harley Quinn Smith as Trace Colelli (uncredited)