York has quite a few.
So I shall be doing my best to think of them all for this. However some that come to mind.

Mr Round-the-corner-from-the-station:
Does the usual lines and so on. "Spare us some change mate?" etc, however one nice sunny day he apparantly was in a crafty mood. He decided to appeal to your softer, fluffier side with a well prepared and thought out line.

Him - "Spare some change mate?"
Me - "Na, sorry mate."
Him - "Do you like cats?"
Me - "..."
Him - "I had a cat once..."

I gave him a quid for the pure random-ness of it.

Miss WHATTHEFUCK - Im still not 100% sure of this but Im pretty sure it was a Miss. You'd see it walking around sometimes, feet wrapped in Tesco bags, dirty old skirt and a bright orange, dirty as hell bomber jacket with no arms on along with dirty green beanie hat. Not too different tramp wise in itself but she had a FUCKING MASSIVE BEARD. I mean seriously, Santa would lay down his sled and bow down to this massive, great grey wiry bastard.

Mr Happy (He actually had this on a name tag): Not as such a tramp, he was a Big Issue seller outside the train station that seems to have sadly dissapeared, he was always dressed in brightly coloured clothes and had obviously done a bit too many drugs in the past. He would greet every one with a huge giant HELLOOOOOOOOOOOO and offer his Big Issue vending abilities. I'd usually talk to him and he'd fall into step besides me for a quick chat as I went to work inside the stations coffee shop. However there was twice that he showed his darker, 'Im-fucking-sick-of-people-ignoring-me' side.

Scene one - A mother with her baby asleep in a pram come past. "HELLOOOOOOO LOVELY DAY!" he goes at her. She just makes a face and signs that the baby is asleep, kindly shut up and fuck of and continues walking past. He turns round to face her retreating back and simply yells. "I BET IT ISN'T EVEN SLEEPING, ITS PROBABLY DEAD." then continues to greet other people happily.

Scene two - Im talking to him and 3 women in that full body Muslim stocking (Hijab?) walk past, he greets them and they soundly ignore him. He turns to me and simply goes "Ah its ok, probably lucky we are outside the station." (they where heading inside) "They're probably bombers."

I miss him :(
(Guilt wants to get in your moist confines, Sat 4 Jul 2009, 14:57, 3 replies)

I used to live in York
So I remember Mr Happy

After York, I moved to Huddersfield, and one day saw him in the shopping centre there. He said he'd been transferred to there from York by the Big Issue people (he lived in Leeds at the time), because people had complained about him shouting "HELLOOOOOOOOOOOOO" at people.
(Dizzy Steinway, Sun 5 Jul 2009, 11:05, closed)

Last I heard
Mr Happy was in Leeds!

I do have some brilliant memories of chatting shit with him & telling pirate jokes a few times walking home after parties :)
(Balue Free From Tetanus, Mon 6 Jul 2009, 18:30, closed)

Ah, Mr Happy...
I remember him too!
(Richard of York gained battles in vain, Mon 6 Jul 2009, 20:46, closed)