Hobo #1, to chick passerby: Hey! Good morning! You should smile more — you’re beautiful!
Hobo #2: She’s not that pretty.
Hobo #1: I beg to differ!
Hobo #2: Hey, man, if you want to go worship her preppy ass, go for it, but she’s not that special.
–Tompkins Square Park
Hobo to passerby: Sir, can you spare a thousand dollars?
Passerby: Haha… Oh you’re serious.
–21st & 3rd
Overheard by: Paul
Swaying hobo with outstretched arms, as it starts to drizzle: I make it rain, I make it rain, I make it rain on you, hoes!
–14th St & University Place
Conductor over PA, on sunny 50-degree day: Due to inclement weather, the 2 and 3 trains will be running on the local track.
–Downtown 1 Train
Overheard by: Ladle
Bag lady: I'm not selling ass, just panhandling. It's too cold.
–9th Ave & 25th St
Really tall dude to no one in particular, very energetically: It's a beautiful day, oh my god! I'm gonna cancel all my appointments and go on a walk!
–2nd & Bedford
Angry stranded guy: And you were all like "it doesn't snow in the city, there are too many cars!"
–Bleecker St
Hobo: I wanna tackle you! I’m gonna tackle you girl! I’m gonna tackle you girl! You hear me? I’m gonna tackle you!
Girl #1: Did he just say he wants to tackle us?
Girl #2: Oh my god! What did he mean by that?
–Spring & Mercer
Overheard by: Spooner
A hobo on crutches hobbles towards a chick walking in the opposite direction, and she swerves to avoid him.
Crutchbo: You think you can outsmart me, bitch? Next time I’ll cut you.
Woman: I’m hoping there won’t be a next time.
–Port Authority
Hobo: Good morning, ladies and gentlemen. My name is Edwin, but you can call me ‘Homeless Ed’… Or just ‘Homeless’ for short.
–A train
Hobo: Hey, y’all! I ain’t gonna lie to you — I am homeless, and I just want a piece of ass, some drugs, and a 40. Ten bucks for a piece of ass? Someone gonna give me some money for some crack cocaine?
–Line outside Roseland Ballroom, 52nd & Broadway
Hobo to horse leading carriage: Dude, you rock! [Gives horse a peace sign.]
–56th & 10th
Overheard by: PetRunner
Crazy hobo: Well, jumping Jehoshaphats! Some homeless person has abandoned his station! I will assume his identity and no one will ever know that I’m rich!
–3rd Ave, between 34th & 35th St
Overheard by: His secret’s safe with me
Toothless hobo on stoop: Excuse me, sir, could you write me a check for five cents and I’ll pay you back on Tuesday?
–7th & 2nd
Hobo: Attention, attention! I’m playing this saxophone to raise money for my spaceship!
Plays a horrible rendition of “Pop Goes the Weasel.”
Hobo: I’m going into space, and I’m taking George Bush with me!
Fellow passengers cheer.
–1 train
Guy to friend: Are you gay, man?
Friend: I'm not fucking gay, I just want to hold your fucking hand!
Hobo: I'll hold your hand, buddy.
–2nd Ave & 11th St
Overheard by: Just wanted a milkshake…
Hobo, to two girls: Hey, Mary Kate, got something to eat?
Girl #1, to girl #2: Ohmigod, did you hear that? Is she the pretty one?
–Grand Central
Overheard by: Commuter
Hobo: You have a quarter for a cup of coffee?
Suit: Excuse me, can’t you see I’m on the phone?
Hobo: I don’t have time for games!
–42nd & 7th
