Bartender Ossington Toronto

Get to know a bartender: Anna May of the Ossington

Meet Anna May. She tends bar at The Ossington. Anna May keeps it tidy and tight during the weekend but fast and loose during the week when things are a bit more local. This stretch of Ossington has seen much change of late from neighbourhood bars to an out-of-towner destination. I was able to sit down with her over a pint or two (much).


Anna May

How long have you been a bartender?

I've been in service for over 10 years. Maybe I started getting bartending experience five or six years ago at the now defunct The Green Room. I try not to keep track. [Ed.'s note: the Green Room is back, but under new ownership)

Name three reasons why you live in Toronto.

1. I'm from here
2. I think a sense of place and feeling of community are most important to me. There's no place like home.
3. High Park

Favorite customer and why?
A fella who lives across (Ossington) street who comes by for cokes and smokes. He talks all kinds of poetry, greets us with smiles and makes us laugh. He's was on this street long before any of these bars were, so you have to respect that. He also calls me Bella, so points for that.

How do you deal with a rowdy drunk?

You catch flies better with honey than vinegar. A smile and a suggestive pint of water when they ask for another can go a long way. If that doesn't work, then call security.

What's your favorite cocktail?

Gin Martinis. Wet and dirty.

Whats your favorite bar or hideout (other than where you work)?

If I tell you, everyone is gonna go! Black Dice on Dundas. They had me at their 25 cent jukebox that plays 45s! I will also check out Life of Craphead when they're performing.

Bartender Ossington Toronto

What cocktail do you hate making the most?

More or less on principle I refuse to make anything called a Pornstar, Juicy Pussy, etc. Second to that are Long Island Ice Teas — you know where someone's headed if they order that drink.

What's the worst thing you've seen in a bar?

This past Halloween someone came to the bar dressed in blackface with a bucket of fried chicken and was immediately shot down, disarmed, washed his makeup off and left. It was intense! Generally though, I've seen people getting hit by beer bottles way more frequently than you'd think.

On your days off, we can find you (doing/at) _____.

Going for walks through Parkdale, Little Portugal, High Park and beside Lake Ontario at Sunnyside Beach — even in the winter.

What's your favorite word for drunk? (Sauced, Pissed, Loaded, etc)

"Juiced" or "all juiced up." It's from one of my favorite songs, Crystal Clear (Beer) by Beck.

Bartender Ossington Toronto


Straight Up or On the Rocks? Straight up

Gin or Vodka? Gin

Light or Dark? Dark

Sweet or Dry? Dry

With a twist or olives? Olives

Lemon or Lime? Lemon

Tonic or Soda? Soda

Labatt or Molson? Labatt

Check out all our Toronto bartender profiles via our Pinterest board

Photos by Christian Bobak

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