Diana Bailey is funny. Like, really funny. A copywriter at a Toronto ad agency by day, the 25 year-old has spent the past two years cutting her stand up teeth at bars, pubs and clubs around the city. This Monday she’ll be one of five comic acts competing for a $5,000 prize (courtesy of the Tim Sims Encouragement Fund) at the Second City’s yearly Cream of Comedy showcase, designed to feature and encourage Toronto’s up-and-coming comedic talent. Acts have already been whittled down from September’s Fresh Meat competition, and past winners of the title have included Pat Thornton, Laurie Elliot and Nathan Fielder of Comedy Central’s Nathan for You. In other words, it’s going to be a good one. We recently joined Diana for a casual gchat to talk wolves, the stand up scene and pregnancy jokes, and to not ask the question “can women be funny?”

Shedoesthecity: So how did you get into comedy?

Diana Bailey: I’ve been doing stand up for almost two years, now. Before that, I wrote sketches for the now-defunct sketch troupe Colonel Mustard.

SDTC: What made you want to start doing stand up in particular?

DB: Well, my sister Laura (co-host/producer of the very awesome Chicka Boom) is a phenomenal improviser,and I’ve been seeing her make people laugh since we were kids. A few years back we were in a sketch troupe together (the aforementioned Colonel Mustard), but I didn’t perform because I had really paralyzing stage fright, so I just wrote. Everyone else in the group thought it would be really funny to give me one line every show, and that line was always, “Are we going to fuck or what?” The only people who came to enough of our shows to know that was a running gag were my super-conservative parents. I thought I should maybe empower myself a little.

SDTC: Who are your comedy idols?

DB: Maria Bamford: she’s so brave and open and hilarious. My sister Laura: onstage, she will commit so hard to anything, even in a skirt. I’ve seen her underwear several times. I think she’s even summoned up a fart for a scene.

SDTC: What makes you laugh?

DB: In no particular order: my wacky Greek family,farts, people whose ambitions exceed their capabilities, pugs, indignant babies.

SDTC: Was there a moment when you realized you were funny?

DB: I was a super dark kid, actually. I was really preoccupied with revenge. I had serious literary ambitions and wrote a lot of poems with wolf symbolism where the wolf was me. I started writing lists of Things I Hate for the school paper and people laughed, and that was way more validating than wolf poems. 

SDTC: What’s the first joke you ever wrote?

DB: I think the first joke I ever wrote was about how I’m afraid of trying to get pregnant and finding out I’m infertile because ten years of anxiety and pill-popping would’ve been for nothing. It’s like going to run a marathon and having an organizer pull you aside and say, “I don’t know how to tell you this, but you don’t have legs.” “Are you kidding me? Do you know how hard I’ve tried not to run before this?”

There’s a reason I stopped telling that joke almost immediately.

SDTC: What’s your favourite joke of yours right now?

DB: Well, it’s pretty weird, I’ll be honest. I’ve got this new bit where I pretend to be a body-snatching alien posing as a stand-up comedian. People either laugh a lot or are terrified, which I think is a sweet spot for comedy. But I get to do an act-out, which is fun because they’re never really exactly the same twice.

SDTC: What would you rather talk about than have me ask you about “women in comedy”? Thai food? Penguins? A bad tattoo you saw once?

DB: Oh, girl. I don’t mind the women in comedy topic that much. While it is occasionally problematic in kind of stupid ways (shitty, sexist intros and the like) I have certainly had advantages because I’m a woman. Most decent producers want to have at least one woman on a lineup, so you get booked for more shows. I also don’t have to struggle to differentiate myself from a hundred twentysomething white dudes. However, as a public service, I will say this: Don’t hit on a female comic at a show. She’s working. She created something personal and now has to share it with a room full of strangers, and that’s nerve-wrecking enough without navigating some weird pseudo-sexual social interaction. I’m sure some ladies dig it, but I’d err on the side of caution. THAT’S MY LADY RANT BECAUSE PERIODS.

SDTC: What’s the deal with your fellow nominees, are you familiar with their work?

DB: I’ve been hosting The Black Swan’s Fan Fiction show for a while now, which the Weaker Vessels are in, so I’ve seen them a bunch of times and they’re incredible. So smart. Nigel is twenty years old and a freakin’ prodigy. And he’s a sweetheart too, albeit a dirtbaggy one. I had seen Franco and Brandon a couple of times before Fresh Meat, but they’re powerhouses too. It’s a stacked show. I’m really excited to be part of it.

SDTC: How would you describe the Toronto stand up scene right now?

DB: The Toronto stand up scene is really creative, vibrant, and in desperate need of some support. The Toronto comedy scene is just as game-changing as the music scene. So Mayor Ford, if you read She Does the City, if you wanna take a trade mission to LA or NYC, Toronto comics would really appreciate it. For the material.

Well, Rob Ford (longtime reader, one day commenter?!?): your move.

Find Diana on twitter at @Epic__Bail. Buy tickets to see her and the other Cream of Comedy nominees here or by calling 416-343-0011.