Winjester Bucket of Comedy Review

This is a recount of my experience at WinJester’s Bucket of Comedy hosted by Michael McLean, a Toronto Stand-up Comedian. I was in the presence of genius tonight.

Jump to: Ordering Coke at a Bar | Comedic Genius | Can I hang with the Pro’s? | Shoutouts

The Approach

The girlfriend told me to bring an umbrella, but the heavens remain closed this evening and my neurosis has me constantly changing the way I hold the umbrella, trying to find the most debonair way to wield the useless instrument.

As I walk up the stairs to the Winchester Kitchen & Bar (located a block from Carlton/Parliament), I hear new age guitarey music kept in stride with a soft drum track accompanied by a woman whining. What genre of music is this? Don’t get me wrong: it’s great background music, just hard to label. Imagine jazz lyrics backed by an acoustic guitarist set to really slow jungle.

I notice the comics immediately, mostly because I’m early so the place hasn’t filled up yet. I scan the room and parse the patrons from the comics immediately; after a few shows it’s easy to discern which is which. I check my phone for a picture of Michael Mclean, tonight’s host, with the hopes of introducing myself before things get under way.


A Man walks into a bar and orders a Coke…

Ordering coke is my norm (clearly, not ‘the norm’), and I coolly respond, “Um, I’ll just have a coke for now” when the bartendress asks me what I’d like. You gotta pretend that you’re starting slow so it doesn’t seem like you’re five years old at McDonalds and your parents are asking you what drink you’d like with your Happy Meal. Michael McLean points out that there’s a guy drinking a Coke at the bar, and that it is not a good sign. Even I, said guy with Coke, have to laugh at that one. Hey, at least it’s not cranberry juice.



Usually, I do a rundown of the acts, but I’d be doing a disservice to the talent I witnessed tonight.

Jeff Leeson was the last comic to go up. He started casually, improvising with the girl that was taking pictures of the event. Then, he went into a prepared routine that he then parlayed into a improvisation with another comic in the audience. Then, he went back to riffing with the aforementioned picture girl.

All this probably sounds pretty run of the mill, but language is a poor witness at times. The genius that I saw tonight stemmed from Jeff’s ability to weave his natural character with his rehearsed material while still connecting with the audience through improvisation. To do that, a certain comfort and confidence is needed so you’re not worrying about what you need to say next. When you’ve been around a few times, it isn’t hard to tell the dedicated comedians from the people just dipping their toes in the water. This guy was a professional.

And I think because of his casual demeanour, that impression may not be left with the average onlooker. But I saw it. It was as clear as day. To end the set, he crafted a conclusion that literally drew the rehearsed material and improvisations together, as if he was finishing an essay and was reiterating his main arguments. That’s genius, man. Think about this: a writer has time to work and rework every word like a surgeon; this guy did it with a beer in his hand.


So where do I fit in all of this?

Whenever I see someone kill, like Jeff did tonight, I ask myself, “Could I do that?” I guess what I’m really asking myself is whether I belong on the same stage as these guys. I think I do. Just because I haven’t done 5 years of sloughing it on open mics doesn’t mean that the stuff I have isn’t on point. People come to different careers at different times in their life, and I couldn’t have come at a better time.

In a lot of ways, I think everything I’ve done up to this point has prepared me for this. I’ve always been a reader and so my writing is a level above the average bear. My business career has helped me organize my comedic life into material (jokes) and management (getting people to notice me). My mind has always been awash with commentary and I’m just now starting to hit the record button. Most of all, it feels right.

No, that’s not right. Most of all, I would do this for free. I haven’t felt that way about anything before.



Thanks to for pointing people in this blog’s direction last night. Promoting artists is a [blue]thankless job, and you do it well.

I ran into Mikey Kolberg after the show, and he gave me great advice on how to enter the Toronto comedy scene. He holds court at, where he also keeps abreast of everything comedic in Toronto.

Stunt like a Baws today,

Michael Jagdeo


About Michael Jagdeo

My name's Michael Jagdeo, and I refuse to write about myself in the third person. I'm a Comedian from Toronto, Ontario, Canada. In addition to honing my stand-up comedy act, I maintain this blog and write the weekly comedy article for
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One Response to Winjester Bucket of Comedy Review

  1. Pingback: My First Set as a Stand up Comedian – Before the Set | Diary of a Toronto Stand-Up Comedian

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