"Monique: [in response to Andrew's flirting] Ew, what are you, hitting on me? Let me put a stop to that little brain fart right now. Girls with asses like mine do not talk to boys with faces like yours."

"Olivia: [When Malcolm, telling her his tarantula is loose, says she should not feed it] Yes, because my first instinct would be to feed the turantula."

"Olivia: [as Viola takes her place at the kissing booth] Beware. The old guy chewing gum... it's not gum."

"Okay, how come when I wanted to ask Eunice out everyone made fun of me, but then Sebastian likes her and suddenly she's cool? Screw you guys. I hate high school."

"[tears up the manual containing the "no girls allowed" policy, before returning it to the referee] What manual? Listen, pal. Here at Illyria, we don't discriminate based on gender!"

"I think I played soccer once, or was it chess?"

"[When asked where the Sebastian is] Well, he must be half way to China by now, he showed us his willis & doodleberries."

"[Handing 'Sebastian' his food at lunch] Have a great apple and sandwich! [The next student steps up and begins to ask for something] No."

"[Seeing Olivia and 'Sebastian' meeting outside his office] What is...? Oh... Getting to know the opposite sex are we? Male female dynamics, all that. Sexual tension... it's all part of the high school experience... Continue, continue, please. But keep it cleaned up. Abstinence is key, abstinence is the best way to not... is to not. Uh- [Pretending to respond to someone in his office] Hm? [Goes back inside his office]"

"Dude, come on, you're a guy, what would you do if the hottest girl in school came and asked you on a date?"

"[to Viola (as Sebastian)] Why, why do you always talk about girls in such graphic terms?"

"[Quoting Coach] Some are born great, some achieve greatness, and some have greatness thrust upon them."

"[To Monique, breaking up with her] You're hot Monique, smokin' hot. But there are plenty of hot girls out there. And the truth is you have nothing else to offer! And when my eyes are closed, I see you for what you truly are, which is UUUG-LAY!"

"I'd tap that."

"You know how it is. New school, new babe pool."

"So, uh, you play the beautiful game... bros... brothers... brethren?"

"[to Duke] What does you heart tell you? [pause] I mean... which one would you rather see NAKED!?"

"Robert Torti – Coach Pistonek"

"Lynda Boyd – Cheryl"

"Clifton Murray – Andrew"

"Brandon Jay McLaren – Toby"

"David Cross – Principal Horatio Gold"

"All you have left is a C-minus GPA with a Wonderbra."

"Tamara Mello — Chandler"

"Dulé Hill — Preston"

"Gabrielle Union — Katie"

"Kimberly 'Lil' Kim' Jones — Alex"