Stupidity

Stupid black guy: I think with Martin Luther King Day coming they should completely end slavery.
Smart black guy: Mmmm…there hasn't been slavery in the US since Lincoln.
Stupid black guy: Oh, there's still slavery.
Smart black guy: Whatever.

–Duane Reade

Teen girl: Oh, I love your nose! What nationality are you?
Middle aged man: Pardon?
Teen girl: I mean, where were you born?
Middle aged man: USA.
Teen girl: What?
Middle aged man: The United States.
Teen girl: (looks confused)
Middle aged man: …of America?

–L Train

Student: Wait. A vaginal ring is one that you wear on your hand, right?
Teacher: No, you know the vagina, the never-ending tunnel?

–Stuyvesant High School

No

Young fashionable hipster girl #1: There's this piece of art, called Piss Christ.
Young fashionable hipster girl #2, interrupting: Oh! Is that the poop one?!

–Houston & 1st Ave

Dude #1: So she called me and told me to get home safe because it was really windy outside.
Dude #2: Damn nigga, it ain't like you paragliding home.

–Flushing

Overheard by: kam

NYU guy: I was totally into Obama until we met Sarah Palin and now she has made me all Republican for her milfiness.
Friend: You know you don't get to fuck her just because you vote for her?
NYU guy: But I can only hope for my brothers in DC. You know like some Bill Clinton intern shit up in the White House, but this time with a hot mother instead of cigars and shit.

–L Train

Overheard by: Nikki

Girl #1: Is “dildo” a word? Is it in the dictionary?
Girl #2: It should be, it's a noun.

–15th St & 5th Ave

Overheard by: Dr.Suze

Headline by: Rosie

Runners-Up:
· “And It’s Not That Hard to Wrap Your Tongue Around It.” – Julian
· “I’ve Verified That It Can Be a Person or Thing.” – Jim
· “Just Look for the Picture Of Bill O’Reilly” – jlp
· “Lesbian Wins Scrabble Contest” – mr. macdog
· “Sure Don’t Script Porn Like They Used To” – benji

Click here to see the new Headline Contest

Drunk hobo: Can I tell you one thing before I die? Babe Ruth was the best there ever was… But I never saw him, and neither did you! Do you know why?
Blonde girl: No…why?
Drunk hobo: Because you weren't alive…and neither was I. (takes out flute and plays Take Me Out to the Ball Game)

–E Train

Angry Spanish boyfriend: You know why I'm talking to you like this! Because your boss was sitting there and you probably had no damn clothes on!

–Broad Channel Subway Station

Girl to friend: Yeah, I can't wait until we take off our clothes and do our make up!

–116th & 3rd

(20-something couple is walking down the street with arms around each other)
Woman: So were you self-conscious when you took off your clothes in front of the children?

–28th & 5th

White guy answering cell: Negrooooo… I'm on the Long Island Railroad being completely homosexual… You missed it, completely naked…

–LIRR

Overheard by: Xavier

Five-year-old girl, before performance begins: Are they going to take *all* their clothes off?

Hair, Delacorte Theater

Girl to friend: God! I remember when my brother ran into my room naked screaming that he had two buttholes.

–Subway, 14th & 1st

Overweight middle age white guy to friend: I know, I get it, you like to sit naked in the mud while some guy serenades you on his guitar singing about things I don't believe and can't understand. That's your thing. I prefer hockey.

–89th & 4th, Brooklyn

Little kid: We're going to the city to get mommy titties!

–LIRR Train

Punk chick: This thing needs bazooms. I'm a punker chick with itty bitties.

–Midtown Office

Girl to female friend: Hey, did you know today is the three-year anniversary of my boobs?

–Union Square

Crazy lady trying to exchange a shirt: I can't go to work with my tits hanging out!

–Abercrombie & Fitch

Overheard by: me neither.

Chick on cell: In his defense, I forget about breasts, too.

–Columbia University

Overheard by: Wild Dog Boy