Hobo to 20-something guy: Who you votin' for?
Guy: I don't vote.
Hobo: You better fuckin' not.
Guy to friends: What the hell is that supposed to mean?
–Little Italy
Hobo to 20-something guy: Who you votin' for?
Guy: I don't vote.
Hobo: You better fuckin' not.
Guy to friends: What the hell is that supposed to mean?
–Little Italy
(teenage girl goes to stand next to her friend in line for the bathroom)
Crazy hobo: Bitch, get to the back of the line! I gotta take a shit!
Teenage girl: Oh, I'm not in line, I'm just talking to my friend.
Crazy hobo: If you don't get outta line, I will take a shit on your chest. Do you want me to take a shit on your chest? Cause I will! (to teenage girl's friend) Oooh girl, you pretty. Why you hang out with cunts like these?
–Starbucks, 6th & Christopher
Subway beggar to the people on train : Yo, my daughter just died and I don't have any money to bury her… (recognizes someone on the train) Yo!
Man on the train: Hey! How's the wife?
Subway beggar: Oh, she good, she good. She be working too! She working on the 4 line!
–1 Train
Overheard by: Faye
Hobo: Spare some change?
Girl: Yeah…so you can go buy booze? Keep dreaming, bucko.
–Times Square
Preppy guy: They say beggars can't be choosers, which makes sense, because we're choosers.
–Madison Square Park
Overheard by: Annie
Red Table change collector guy: Help feed the homeless of New York! All it takes is a penny and a heart, you fucking assholes.
–Times Square
Overheard by: Bemused
Girl to friend: I thought of you the other day; I saw a homeless man's penis.
–Lucky Jack's, Orchard St.
Overheard by: Argopelter
Horny dude (after being rejected by a girl at the bar): I asked her if she wanted a drink and she gave me the look that I give to homeless people on the subway.
–79th & Broadway
Guy to girl sitting at a sidewalk cafe: I know, what is with her? She dresses like a homeless person. And not Mary-Kate Olsen homeless but I-think-I-saw-her-passed-out-in-an-alleyway-with-a-heroin-needle-sticking-out-of-her-arm- homeless.
–10th St & 2nd Ave
Girl, to guy who has just spat on floor: Don't do that! Homeless people sleep there!
–6 Train Station
Hobo #1: But that's not enough to have pee in my butt…
Hobo #2 (interrupting): What would have been enough? 30, 40 dollars?
Hobo #1: Huh? Well! What the hell are you asking for? Now, exactly, you can pee in my butt for nothing…for a conversation… for a howdy do!
–YMCA
Overheard by: German Deter
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
Hobo to another: Ohh… Check that out! Hot white ass!
Girl in blue pants: Why are there so many drunken perverts in Central Park?
Friend (seriously): He's probably just color blind.
–Grand Central Station
Headline by: dwasifar
Runners-Up:
· “…Or, Knowing Your Ass, Just Plain Blind.” – EddieA
· “Because Let’s Be Honest, He Clearly Wasn’t Referring to That Wagon You’re Dragging.” – Wilkeson
· “Or It Could’ve Been the Ablino Donkey Behind You…” – Krikit
· “Smurfette Swore She’d Never Come Back to the City Again.” – 1310 (formerly SNA)
· “The White Pants…Always Keeping the Colored Pants Down” – California Dave
Hobo, interrupting a guy and a girl: Excuse me, could I bum a cigarette or get some spare change?
Young man: I'm low on cash and sorry, but I have a cigarette for you. (hands hobo a cigarette) Do you need a light?
Hobo: Nope. (walks away)
(young man and woman continue conversation, hobo comes back and interrupts again)
Hobo: Can I ask you a question?
Young man: Shoot!
Hobo: What does Matt Damon's dick look like in Audrey Hepburn's ass?
Young woman: Trick question.
(hobo gives them the finger, walks away)
–Central Park
Black hobo to passing tourist: Where you from?
Tourist: Ireland.
Black hobo: You Irish?
Tourist: Yeah.
Black hobo: Well, god bless the Irish. And god bless the Italians. And fuck everyone else!
–8th Ave & 22nd St
Overheard by: Doug Tischler
