... so I had this guy TOTALLY convinced I was a cop!

I was crossing Portage, when a young man on a bicycle approached me. He was maybe in his early twenties, or younger, with waist-length blond hair and smelled noticeably of beer. In general he looked like he would fit in very well in 1967.

Hippie: Winnipeg Police! Winnipeg Police! Hey.
Me: [slows down, but does not stop]
Hippie: Hey, I'm with the Winnipeg Police, uh, I've got my badge right here [reaches for his back pocket, but doesn't take anything out] Uh, let's cross the street. Yeah, cross the street.
Me: [thinking] Why is he pretending to be the police? Where is he going with this?
Hippie: Where did you get that ... uh ... jacket and book?
Me: [thinking] Is he going to try to mug me for a water-damaged copy of Foucault's Pendulum? I haven't finished it yet!
Hippie: So I'm with the Winnipeg Police...
Me: [keeps walking]
Hippie: So you've been ... uh ... you've been seen dealing drugs. You've been dealing drugs, right?
Me: [laughing] No.
Hippie: Hahaha! Just kidding man! F*** those guys! [bikes away]

That's where we keep the VHS

Repairman: Why is it so hot down here?

Employee: Well, there is that portal to hell...

-overheard at blockbusters on broadway

I wasn't worried. NOW I am...

A guy is walking down the street with some helium balloons. Another guy, out for a smoke stands behind him. Then out of nowhere:

Smokey: Don't worry, I'm not going to pop your balloons.
Balloony: ... okay.

-overheard in west broadway

Jumping Jacks?

(Cold couple with coats rounds the corner in a darkened alley)

Scary-looking Cold Couple: Hey, let's jump those people and jack their coats!

Cold Couple with Coats: ...

SLCC: Just kidding! Hahahaha!

CCC: forced laugh

SLCC: My coat is nicer anyway.


-overheard in west broadway

Why did the drunk guy cross the road?

Noticeably Drunk Guy: ... well, I'll admit I'm a little drunk. But I blame the creator. Because I'm BALD! (laughs hysterically) [he's not bald]

Noticeably Sober Guy: ...

NDG: Hey, a joke, a joke. Why did the pygmy cross the, uh, cross the road?

NSG: I don't know. Why?

NDG: Because he wanted to commit suicide! (laughs hysterically. Then, suddenly serious) Do you want to come have a beer with me?

NSG: No thanks, I don't drink.

NDG: (look of disbelief) What...?

-overheard in west broadway

I forgive you. This time.

FSD has appointed himself the doorman of our building. He waits on the steps, in the shadows, and when he sees me approaching he hurriedly unlocks the door.

I'm not sure if he thinks I don't have a key, or if he simply enjoys being helpful. I'm also unsure if he opens the door for everyone or only for me.

Recently I came home and walked in the door just after him, unlocking the door with my own key as I did so. When he saw me enter, he turned and said "Oh! I'm so sorry! Please forgive me, it won't happen again!"

So THAT'S what chaps are for

Leathery Man: There's nothing better then a wet crotch when the rest of your pants are dry.

-overheard in a broadway pawn shop

The Other Penis Man

Thanks to Jaimie for the submission.

He was saying I have a fax from Cape Breton. Didn't you take a message?

I don't know if he was following me around, or what, but I saw Buster the Disowned Rankin Brother in two different parts of the city today. Both times he was cheerfully singing at the top of his lungs. The second time he talked to me for a while, and I would transcribe his conversation here, but I couldn't make out a single word except "Halifax" and "Cape Breton".

Was he perhaps claiming that Halifax is on Cape Breton Island? Was he telling me that he is from Cape Breton? Or from Halifax? Was he telling me that that's where he's headed? Some things science cannot answer.

Did you know I hate old people?

Old Bigot: Did you know I hate Indians?


-overheard at in a tim hortons on maryland

Reindeer Games

Hairy the Dog Man was—in his habitual way—walking down the street puffing on his pipe. With him were, as usual, his two white fluffy dogs. Both were dressed in Christmas sweaters, with wings attached to them, and wearing reindeer antlers.

"On Dasher! On Dancer" cried Hairy. He looked at me and, in an explanatory way added, "they shrunk in the wash."

Gratefully Blonde?

Hairy the Dog Man is a thin man who is often seen walking down the street in West Broadway. He is rail-thin, has long hair, a full beard and looks like an aging hippie. He usually puffs ponderously on a pipe, while walking very slowly.

With him he has two small white fluffy toy dogs; possibly bichon frisés or toy poodles. Sometimes the dogs are running freely at his feet, and sometimes he is carrying one or both of them.

He's like a strange cross of Jerry Garcia and Elle Woods.

But he's got a great personality

Flameshirt the Shadow Dweller has been mysteriously transformed into Noshirt the Sunlight Dweller. Yeesh.

But it's only 7:30! The sun's still out!

My wife and I bought roller blades at Value Village recently, and we wanted to test them out. So we went roller blading around our neighbourhood. In the course of our excursion, we passed by Flameshirt the Shadow Dweller. We stopped to rest on the steps, and FSD stepped out of the shadows to talk to us.

FSD: There was someone killed in this neighbourhood. Just a few days ago.
US: Yeah, well...
FSD: And there was a murder just around the corner before that.
US: Well, Winnipeg is Canada's Murder Capital.
FSD: You shouldn't be out late. Returns to the shadows from whence he came.
US: ... thanks for the tip.

Meet the Weirdos

Broadway Bizarros

Flameshirt the Shadow Dweller: A creepy old man with (apparently) only one shirt who likes to hang out in the shadows of one of the apartment buildings in West Broadway.
FSD's appearances: 1, 2

Hairy the Dog Man: A greatly bearded, long haired man with one pipe and two toy dogs.
Hairy's appearances: 1, 2

Buster the Disowned Rankin Brother: A cheerful panhandler often seen at Osborne and Broadway, who sings loudly and mumbles incoherently.
Buster's appearances: 1

Osborne Oddities

The Penis Man: A panhandler in Osborne Village who is often accompanied by his very drunk sidekick. Got his name when he claimed that he needed money for a penis reduction.
The Penis Man's appearances: 1

Yappy the Aggressively Cheerful Woman: A panhandler in Osborne Village who often sat outside Movie Village, and cheerfully (but aggressively (hence the name)) asked passers by: Gotanysparechange? Maybeonthewayout?
Sadly, she passed away in fall, and the city was deprived of a little bit of its colour.
Yappy's appearances: 1, 2

Exchange Eccentrics

Mr. Thirsty: A discheveled looking man in his mid-to-late forties spotted from time to time in the Exchange District.
Mr. Thirsty's appearances: 1, 2

Distinctive Downtowners

B.G.: A frail,intense-looking man of around 80 whose initials really are B.G.
B.G.'s appearances: 1, 2

Miscellanious Mischief-makers

The Pig-Man: A Fort Gary resident whose turned up nose, pointed ears and beady eyes apparently make him resemble a pig. There has been some skeptism expressed in the comments as to the actual existance of the Pig-Man, but the original submitter of the story is adament that it is true.

Bus Crazies

These weirdos deserve a class all by themselves. They defy geographical classification (and alliteration). Ever been on a bus and notice that the person sitting in front of you is talking a little too excitedly? To no one? Ever see someone get into a screaming match with the driver over 5 cents? Then you know who I'm talking about.

Crazy Kids

We used to do this feature where we had children's quotes on weekends. We don't do that anymore, but you can still read the ones that there are from, you know, the past.

The Trike Guy

Rough looking dude with long hair, handlebar mustache, etc, who drives around the city on what is clearly a homemade motertricycle.