S&M, bestiality, and voyeurism all in one go.
Manhattan: My mum said to me ‘What’s with all the surprised ladies in large cars?’
Facelifts!
And apparently quietly preaching salvation on his commute home. I have to give him major props for the smooth silvery mask/makeup/whatever the hell he had going on. It was a stunning contrast between that and the well-worn-looking clothing/armor he had on, but an outer costume stored away makes sense.
People passed out on the sidewalk and other people walking around them is no big deal; we just call that “The Stampede” here. 
I’ve seen that guy across the street from Union Station in a hoodie that has writing scrawled on it like “No child left behind.” Without knowing the situation at all, I assumed that he lost his children in a custody battle. He doesn’t act up or say anything and I’ve been tempted to ask him.
I live in Chicago but I don’t usually see crazy stuff. I’m not sure what I’m missing. Several years ago while sitting in a bar I saw an older Hispanic woman walking up and down the sidewalk carrying some sort of cross that had construction paper with a bunch of photos taped to it. Through the window, I gave her a “what’s that for?” kind of gesture and she responded by flipping me off and continuing on her way. At first I though she was crazy but then she may have just thought I was some drunk jackass at a bar giving her grief. The truth may be somewhere in the middle.
At Millennium Park a few years back, I saw some guys who were wearing this power armor kind of get up made entirely out of bleach and detergent bottles. They must have had 100 bottles each and it actually looked very cool. Not really crazy, more like a performance thing, so it doesn’t really fit the OP so much.
I dunno, freakout/mindfuck street “performance art” really only can be done in dense urban areas so why not have them count? I once saw three people in large, full-body rabbit suits (not Bugs Bunny, just Generic Athropomorphic Lapine) enter into a midtown deli with a large “hot buffet” area and just walk around, saying nothing and buying nothing, before exiting and going into a McDonald’s next door. No reason given or asked. They were just people in bunny costumes.
Random subway musicians can be quite memorable too. For a while, my commute would have me regularly pass an old Chinese guy playing an erhu very well on one level, then on another platform level (to change for another train) I’d often see an old black man expertly playing licks on a blues harmonica. Then one day, they apparently discovered each other and were jamming in a really interesting blend.
On the down side, I can still recall with gritted teeth the two guys doing a cover of Led Zeppelin song “Ramble On” with bongo drums and tambourine while singing in almost, but not quite two-part harmony. That’s all they did, like in a tape loop. So if my train didn’t arrive within 3 minutes, which was most of the time, I got to hear it again, and again.
I don’t really see the weird stuff so much, I’m afraid. I do find the Mitzvah Tank, which has been patrolling around my nabe during the holiday, to be slightly weird and amusing, but that’s just 'cause I’m a boring white boy from a boring white town. And there’s a nifty band I discovered when they were playing in the Union Square subway station.
Here are a few of mine
I was on the subway and a young man was doing magic tricks for spare change. He approached me and told me to make a fist. I did and he put his hand on top of my fist and moved it around a little bit. Then he asked me if I had anything in my hand and I said, “no of course not”. Then I opened my fist and and released about a half dozen nerf balls. And to this day I have no idea how he managed that without me feeling a thing.
Another subway tale -sort of amusing and really sad: I was sitting across from a middle-aged woman with a child that was about 8 or so. The girl was obviously unwell in a chronic way. Her mother turned to her and said, in a comforting tone " It’s going to be OK, honey. They say when this lady prays for you her hands bleed like Jesus’s".
In the same vein, once when I was working at the Circle in the Square theatre on Bleeker Street we had the front door of the theatre wide open while we were setting up, this allowed for a view of the empty stage from the street. A homeless man that was walking down the street walked in, went up on stage and started performing the mad scene from King Lear. He was really good, and I think all the wanna-be actors working with me went out and got real jobs the next day.
Some work friends of mine were in town for a convention and staying at a midtown hotel. As they approached the entrance to the hotel one evening, they witnessed the doorman in what appeared to be a screaming fight with another guy. It actually looked like it might turn physical, so my friends were scared to approach the hotel entrance, they were standing near it with the stunned “what do we do now” expressions on their face. The the two guys saw them and abruptly stopped yelling and started laughing. They said, “We’re friends, we were just playing around”…then they took my friends out to dinner at the Carnegie Deli to make up for scaring them.
Then there is the chair story. One Sunday morning at about 8AM I was walking through the Chelsea area when I saw a man in ragged clothes and no shirt walking down the street with a kitchen chair on his head…one of those mid-century ones with a vinyl seat, metal legs and a vinyl backrest. It was positioned so the seat was on the top of his head, the backrest was behind his head and the legs were sticking straight up. He seemed to be very happy and was singing, ( with a suprisingly good voice)the Johnny Mathis’s song “Chances are My Chances are Good”.
The next night I was at dinner with a half dozen acquaintances and I told them about the guy with the chair on his head, and every single person at the table had their own story about a guy walking down the street with a chair on his head.
Once at Port Authority on Saturday morning, boarding a bus to visit friends in New Jersey, there were two young hookers behind me in the line to board the bus. One of the girls was acting like she was still at work, shaking her booty (as it were ) and eyeing the men. The other girl was a little embarrassed by this and turned to her friend and said " We’re getting on the bus, you gotta be low key" and Hooker #1 gave another shake and said in a loud voice " Low key don’t pay the rent!"
Aahh… New York… and for what it’s worth, Aahh… Los Angeles, New Orleans, DC, San Antonio, Baltimore, Miami, Seattle, Austin, Philadelphia…
Check out the Overheard in New York site for some more random encounters.
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Ye gods, thank you all for reminding me why I don’t live in a city {shudder}
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Hey, at least in the Urbs we have the, erm, Interesting Characters right out there where we can see them. Inexpensive entertainment!
[QUOTE=LawMonkey]
I don’t really see the weird stuff so much, I’m afraid. I do find the , which has been patrolling around my nabe during the holiday, to be slightly weird and amusing, but that’s just 'cause I’m a boring white boy from a boring white town.
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Heh, that’s one that got a smile out of me actually (and BTW, the retirees now have some really spiffy Chabad synagogues-on-wheels down in South Florida, too. I always figured, you must have some goy driving on Friday, lest you have to pull over and be stuck by the side of the road if you’re running late…).
Now, THAT is a theater story.
Homeless Kings Lear, stigmatic faith-healers, people who feed strangers plums, insane cabbies, Rollerina and the Naked Cowboy, chairheads, hookers with a work ethic… truly the building blocks of a great community 
I was coming home on the subway when a sort of unkempt, shambling man entered the car. I resigned myself to being hit up for cash. I NEVER give to sob-story beggers and actually, I didn’t have any cash on me.
Instead of the rambling tirade I was expecting, the guy started freestyling about chicken. He was good, too. It was actually so awesome I searched all my pockets and the depths of my purse and came up with 0.42 to give him.
Had another interesting experience the other night, at an End of the World heavy metal show.
The singer of this one band is just as gruesome-looking a human being as you can imagine: scraggly long blond hair, tattoos everywhere, freaky clothes, the works. He approaches me as I stand beside the stage and says, “Be careful! I don’t want you to get goat’s blood on your white coat!”
And yes, the goat’s blood was real.