22 Questions With Comedian James Cunningham, Awards of Excellence MC

James, tell us who are you in three words or less?

1) Bald 2) Funny  3) Guy

What was the best comedy show you ever attended?

I was in New York City a few years ago and I stumbled upon a Broadway theatre where Dave Chappelle just happened to be recording his latest special. I impossibly got a single ticket! Even better than the fact that Beyonce, Jay-Z and tons of celebrities were there—the opening act was Bill Burr! It was the single best night of comedy I’ve ever experienced.

Where was your best gig of all time?

How could you pick just one? Every IBAO Awards of Excellence Gala of course!

Where was your worst?

Well, there was this one time I was hosting this big show in Ottawa for this association—I forget who it was—and they had me in this Mountie costume. But, the costume rental place gave me the wrong pants. Although the jacket fit, I had these weird small pants around my knees the whole time. What a fiasco that was!

How many years have you been working with the IBAO?

Probably since its inception. I have to research that a bit more. I may be off a few years.

What was the worst job you’ve ever had?

Pool boy when I was in high school. I thought it was going to be a summer of looking at cute girls in bikinis and it turned out to be scooping a lot of dead squirrels out of pool filters.

You’ve been a comedian, actor, tv show host, cookbook author, pool boy, and host at the Awards of Excellence—what role have you not tried that you’d like to tackle next?

Insurance broker of course! A guy’s gotta dream!

You were the host of Eat Street for five years—what’s your favourite meal you had on the show?

This is a tough one, but—hands down—there is a food truck in Austin, TX called Gordo’s Donuts and literally everything from that truck is incredible. It’s not just donuts, as the title implies, but every meal somehow involves a freshly made donut. When you order the cheeseburger, the bun is made of two donuts—soooooo good!

What Toronto spot would you recommend to out-of-towners who’ll be visiting for the Convention?

They have to check out Kensington Market. There are so many great new and established restaurants—there’s something for everyone to check out. Egg Bae for great breakfast sandwiches, Crumbs for great fusion Jamaican-style patties, and Burgernator for the best and sloppiest burger. Also, if you’re gluten free, there is a great 100% GF bakery called Bunners!

What’s your favorite country you’ve traveled to?

Though it sounds cheesy, our neighbors to the South always surprise me whenever I go. Whether it’s New York, LA, Miami, Vegas, Austin, Washington—there are so many great cities in America and I always find something new and exciting.

What country have you not been to, that you’d like to see?

I want to go to Spain and particularly the Basque region—I’ve heard so many great things.

You have an adorable whippet named Olive—what was the inspiration behind that name?

Olive is my third whippet—it’s my breed of choice and I have another girl on the way, so the real question is what name goes with Olive?!?

Who’s the most famous celebrity you’ve met?

Gosh…so many—Arnold Schwarzenegger, Bill Clinton, Howie Mandel, Kiefer Sutherland, Hilary Swank—the list goes on and I never get tired of it.

Who’s the nicest celebrity you’ve ever met?

John Pinnet—he’s no longer with us, but what a great comedian. I opened for him about 20 years ago. I’ll never forget—after the show he came into the dressing room and said, “You’re a very funny guy and you’re going to go far!” Then he tipped me $1,000 US which, at the time, was more money than I even knew what to do with!

What TV show are you currently obsessed with?

Currently obsessed with a few but Yellowstone, Insecure and Curb your Enthusiasm are my current top three.

What’s the last movie you saw that blew your mind?

Top Gun: Maverick! My expectations were high going in and wow. I gotta say, Tommy Cruise delivered.

What podcasts are you listening to?

I listen to Smartless, Joe Rogan (only the comedian episodes) and WTF with Marc Maron.

What new hobbies/interests did you pick up in the pandemic?

Butter churning.

What’s an interview question you’d always wished someone would ask you?

“James, what’s it like to be so funny and yet so devastatingly handsome? I mean, how do you do it?” Sigh. Maybe one day…

Okay, so what’s the answer to that question?

I don’t know. I just do it. Does the Mona Lisa know why it’s such perfect art?

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