Before we announce the winners of the 2017 MyEntWorld Critics’ Pick Awards, we’re proud to present our annual Nominee Interview Series.


In her review of his set at the Toronto Sketch Comedy Festival, Mary-Margaret said “Until seeing Jon Blair at Sketchfest, I was unaware that there was a void in my life. I now question if you have seen comedy until you have seen his Triple Crown character rap about how much he wants to be a horse”. This quote perfectly captures the particular quirk and unquestionable brilliance of comedian Jon Blair who is the only solo performer ever nominated for Outstanding Sketch/Improv Production. His writing is bold but thoughtful, his performance style is an effective blend of affability and bravura, and his ability to make a crazy idea work is second to none.


Do you remember your first experience with theatre?
Well, my first experience in theatre was a lot of school plays. I was a real school play kind of guy. Any time there was an opportunity to do a performance thing, I was always up for doing something like that.


What were some of your starring roles?
Oh, boy. We did a play that was just a bunch of songs – mostly from musicals, but some not from musicals, and they did “Mr Sandman”, and I was the Sandman. And I’m a disastrous singer, and I can’t sing at all. Not even when I was a kid. My only line was “Yes?” They’re like “Mr. Sandman”, and I go “Yes?” and that was my whole part. So, good enough for me. [laughs] When I was a kid and, shamefully, into my adolescence and adulthood, I would really obnoxiously stay up and watch Saturday Night Live and The Kids in the Hall, watch a sketch I didn’t get, and then recite it verbatim the next day to my very bored friends [laughs]. I’m glad I found a gig where that’s okay. But I think my first experience in theatre was whenever anyone would let me get in front of them and do a thing. It’s incredible to me that anyone was my friend before I was, like, 24.


Who are some of the artists who have always inspired you?
Kids in the Hall, in a big way. I always really liked SCTV. I’d sit in front of that before I was old enough to understand anything that was being said, language-wise, I wasn’t a baby, but I was like, “I don’t get any of these jokes, but I love it. I love that people are being funny.” Martin Short was always a really, really big inspiration to me, comedically. I don’t know if I really do his kind of thing now, but he was my favourite guy.


You’re a regular contributor to The Beaverton. Do you have a favourite article you’ve done for them?
Okay, it’s stupid, but my favourite article I’ve ever done for them was sort of a response to this reporter for Info Wars. He’d been given the finger by a 9-year-old girl on the Internet, and everyone was laughing at him. And he recorded this big, long video about how he wasn’t, like, owned by this kid, and everyone’s like, “Guy gets owned by little kid!” And he’s like “I was not owned by this little kid, and here’s why”. And he just dug deeper and deeper and deeper, and made this tremendous hole for himself.


I did an article, and there was an editorial by Goro from Mortal Kombat talking about “Here are 3 reasons why I wasn’t owned when Johnny Cage dropped it in this place and punched me in the genitals”. I pitched this at the meeting, and they were like, “No.” [laughs] “Well, what if I bring it in?” And they were like, “Bring it in. And then we’ll listen to it. And then we’ll say no.” And that’s exactly what I did, and they went “Damn it, all right. Fine, we’ll put it on.” I think the only reason it’s my favourite is because I beat how stupid an idea it was. [laughs] And that was it. I was like, “Yes. I wasn’t supposed to have been able to do it, and I did,” and that’s the only reason that was my favourite. Because that’s all I’ve ever really tried to do – be like, “This should be terrible. I’m going to try to make it good and see if it works. And if it doesn’t work, I’m just going to run away”.


in a sketch for This Hour Has 22 Minutes

You also spent a few years on This Hour Has 22 Minutes, which is on CBC but also is a satire show. What are some of the challenges of working for a government-funded organization, while criticizing the government in your comedy?
[laughs] I think the biggest challenge in that is that it’s kind of theoretically impossible. There are just so many places where you just never go, and a lot of that, with a show like 22, is absolutely that it is government-funded, “the state broadcaster” opponents are calling it. But it also has this mandate to have this really broad appeal. So what you’re saying has to appeal to as many people as possible, all across Canada, at every age demographic. So it has to be a digestible message for literally everyone, and I don’t know how you do that. I think the reason that I don’t work there anymore is that I never figured out how you do that. 


I’d stay up late at night writing sketches, and I would always say that if I was writing something and it made me laugh-  like, if I was typing something, and I laughed out loud and was like “Oh, that’s good!”- I was like, “Oh, this one’s dead. If I like it, it’s not getting through.” But it is tough, because you’ve gotta appeal to everyone in the country, and it’s gotta make sense. Everyone in the country has to get the jokes, so you’re painting with as broad a brush as possible. 


I will say, there is a real sea change in the show, because the tail end of my working there was just as Trudeau got elected. To be honest, I’d love to say that it felt impartial, but I went from 3 years of just hammering the government every day to all of a sudden, you know, maybe they’ve had time to change tack now, but it was like, “Oh, we’re not going at these guys the same way, are we, necessarily?” It’s very difficult. I think the show is great, and they’ve been doing a great job for so long. But it is tough when you’re in it with a national broadcaster, and the nation changes year after year after year, and you have to kind of approach it with an even hand. It is tough when you’re trying to do a show for literally everyone.


So you’re doing your own solo show, where you can write literally anything you want. Where do you start? How do you even decide what you want to do if you have all these options?
I find that that’s actually pretty easy for me, because I don’t leave any idea behind. I dig through my own mental dumpster all the time, just for any one line of something, or a little idea. I will pull it out and be like, “No, this is good, I can make something about this!” and then I will come up with a 5-minute sketch about that. Or maybe some idea that I had really briefly for 22, or something I did for the Sketchersons, when I was with the Sketchersons, it was a two-hander, and I can go, “What if I took this idea and sort of scooped it out of there, and put it in something else?” The one thing I will say about me is that I have the patience to just dig through my own trash and make a whole show out of it [laughs].


You’re nominated for your performance at SketchFest. How did that show come together?
Some of that stuff got workshopped for a long time, a lot of things from I’m Only One Man, which is the hour-long review I did a year before. It was a few new things. A lot of it was just things that I’d tried on some other people’s shows. “Triple Crown”- one of the bits that I did there, which is a rap bit- I did at Rapp Battlez originally. A lot of it’s just refining, refining, refining, getting in front of as many audiences as I can. Figuring out what works and figuring out where I’m waiting for a big laugh or something and don’t get it, or if something that I’ve done a certain way gets a response that I wasn’t expecting.


A lot of my stuff is almost prose, it’s almost monologue-ish. I have started billing myself as a solo sketch comedian, so a lot of it is just writing it like I would write a prose piece, or a speech, or an article. I try to make it sound more like it’s coming out of a human mouth than something like a Beaverton article. I sit down, and I write way more than I need to write, and I come up with something which is way longer than it needs to be, with a lot of spare parts that it doesn’t need, and then I figure out what can go, basically.


Do you move things around to find exactly the right structure and the right pacing?
A lot. I’ve had a lot of things where I hit this kind of energy high point too early, then I’m like “Oh no! Now I’m trapped here, and I can’t scale it down because I’m getting near the end.” A lot of my comedy, too, really asks the audience to sit through a setup and hope that it’s going to pay off. And I’d like to think that it does, but I don’t want them waiting around for the drop for too long, you know? [laughs]


There’s an absurdity to your humour. What’s the furthest you’ve ever pushed it, and what are some interesting reactions you’ve had?
One piece I’ve been doing for a while, and have started to put into my rotation – it’s kind of a seasonal one, I can only really do it around the holidays- it starts with a lengthy speech of a man on a phone trying to reconcile with a woman who’s left him, and he’s talking about how his music career’s finally taking off, and stuff like that, and it blows up in his face, and it goes terribly. Then he walks into a room, and that Chipmunk Christmas song starts playing. And it turns out that he’s Dave, the Chipmunks’ surrogate dad, and he’s just recording them doing this song while he just sits there crushingly depressed, and it just gets worse and worse and worse. The first time I ever did that, I had the genius idea to try that at a burlesque show. It’s the worst anything I’ve ever done has gone over, I think. Everyone just sat there being like, “Thank you, leave the stage, please”. That’s a matter of knowing your audience, [laughs] which maybe I didn’t at the time. 


There’s a sketch I do where I do a very bad theatre audition that involves a lengthy song. And I do it twice, so if they don’t like it the first time, I’m like “oh boy, well – we’re taking that exact same trip again.”


Speaking of knowing your audience, have you had dramatically different reactions to certain bits depending on where you are performing?
Generally, it’s been pretty uniform. I think generally people are pretty game for what I do. I try not to make them feel like I’m going to hang them out to dry for too long before I give them something to laugh at, and thank them for their patience.

I was in Halifax with a friend two years ago. That was interesting because I think a lot of the people coming to that show weren’t necessarily the crowd that would normally come to a show of mine. They were that sort of weekend afternoon crowd. I’d gotten a slot at the Company House, which was a really great pub where I’d done a lot of shows back when I was living in Halifax. I’d gotten all the late slots, and I figured “I’m going to be this late show that people can go to!” and no one went to those. They went to the ones in the middle of the Sunday afternoon, and were like, “Oh, let’s see what this is.” Some things still worked really well, and some things didn’t, but that was the kind of trial by fire where, out of that, a few sketches were like “Well, if the people who didn’t know what this was going to be, and weren’t into the rest of the show, still liked this, then this is a staple, this is in everything.”


Jackson on People Watching

Tell us about People Watching and your role in that show.
Oh, People Watching is great! I’m so happy that you asked about that. We just finished recording for the second season, and that’s going to be coming out soon. I had a really, really great time working on this season. I really liked working on the first one. They gave me a little more to do in this one, which was really cool. It’s a bit more of a dramatic turn for me this time around. I play a character called Jackson, who is a 20-something guy who just really seems like he has his life together, and has the outward appearance of being really collected and stable, but he’s a very lonely person who has a very hard time with social interaction, or reaching out to people. Because he looks like everything is fine, no one ever makes the effort to approach him, because he seems like, “Oh, this guy’s got it all together”. But nothing could be further from the truth, so a lot of his arc is him just trying to join the world a little bit. Which is something I kind of can relate to, as a person who frequently puts myself in little boxes. A lot of what I’m doing now is just stuff by myself. That wasn’t always the case, but I went, “No, this is what I like. My little thing to work in.” So, maybe not to that degree, but I do find that relatable, that it’s easier to just sort of sit in your little closet for a bit. 


But lately you have been working in a group setting a bit more- you’ve been doing a lot of work with Sex T-Rex. What have been some of the highlights of your work with them?
Oh, wow. It would be shorter to say what I didn’t like.


You can do that too.
[laughs] Mostly just all that time in the van, that was the only thing I didn’t like.


But to actually answer the question… I saw SwordPlay, and [Watch Out] WildKat at once because Danny Pagett had just hired me on to do Hangman. I knew he was directing it, and I was playing opposite Kaitlyn Morrow– she was my puppet son- but I didn’t really know either of them yet, so I went to go see what they did, and it blew my mind. I became really good friends with both of them over the course of Hangman, and we were kind of travelling together when we went with our separate shows to Halifax Fringe. It was amazing. I owe Danny several times over – he couldn’t do the tour this year, because he was doing Cloud, so I went with them on the tour, because they’re like “Well, Jon’s seen the show a million times.” It was just over the last year.


Working with them has just been changing my overall trajectory in a really amazing way. I’m just in awe of them all the time, and I love what they do, and to be able to do it myself to the degree that I have, and to see how they make it, and to be a part of doing something new… We went across western Canada, this summer, and it was unforgettable. I will literally not ever forget it. Just doing that show so many times, and always trying to find new things, and always trying to find new ways to do it. Except for Halifax, that was my first time doing an out-of-town Fringe.


It’s been really amazing working with them, and feeling like I’m a part of a thing that is maybe larger than what I do on my own. It’s a really nice reminder of the rest of the world, and it’s amazing to be around that much creativity. And to be working with people who are not only now really, really good friends of mine, but people I admire so much. And when I go back to my own work, I’m not distracted by it, I go back to my own work with a new energy because I’ve plugged myself into other people, and I’ve gotten that sort of energy and creativity off of them. And I feel like my own work is better for it, rather than just living in a little vacuum. That was probably a really rambly answer but it’s been really tremendous to work with them, and I hope that I get to again soon.


What else are you working on, or what’s your next project?
I’m trying to write a web series right now, tentatively called Let’s Fight on the Internet, which is like a 1990’s instructional AOL CD-ROM kind of tutorial about how to successfully argue with strangers on social media. [laughs] The research is deeply unpleasant.


And, this will probably be out soon, or hopefully coming out pretty soon- I’m working on writing and drawing a short series for CBC Comedy called What It Was Like, which is a series of short speculative fictions about events soon to come, and the 21st century. It’s kind of dumb Black Mirror


So like a retrospective of things that are yet to happen?
Yeah! Exactly. Just an old person near the end of the 21st century explaining the time that this thing happened in 2035. So it’s a bit of a roundabout, but it’s been really nice- I used to draw a lot, and it’s been really cool to get back into just sitting and working on that.


Do you have anything you’d like to add?
I would absolutely like to add that I’m very happy to be nominated in this category. It hasn’t escaped me that I’m nominated for a SketchFest set alongside stuff like this amazing Second City review, and Peter n’ Chris, and all these great shows like Bad Dog, and 32 Short Sketches of Bees, and just wonderful, fantastic shows. It’s pretty terrific to be mentioned in the same breath as them, just for my thing that I get up and do myself whenever I can in front of people for fun. It’s pretty amazing, so thank you.