An Interview with Trans Comic Carey Callahan

SEASON3I’ve gotta admit, I’m a standup comedy junkie. So much so that I’ve even produced a comedy show (or 2 or 12). It’s one of those talents, like being able to whip up a 4 course meal for 6 out of a few condiments in a busy bachelorette’s fridge, that leaves me in awe and full of appreciation. I don’t know how comedians do it. It’s not only about coming up with something brilliant, witty and unique. It’s standing up in front of people, with the very real possibility of totally bombing, that makes them a kind of heroine/hero in my book. Each one has to come up with their own twist on things to help them stand out in the sea of funny folk. Well, Carey Callahan has surpassed most in being unique. Carey is a trans comic from the west side of Cleveland. No, it’s not the “being from Cleveland” part. I would imagine a phenomenal sense of humor would be needed in general to be from Cleveland, given all the ribbing they get. It’s being trans and going thru transitioning 6 years or so into their journey in comedy. It takes a lot of guts to be a standup comedian and even more to stand up for what makes you happiest and more comfortable in life. So I guess you can say Carey Callahan is a special kind of hero and I can’t wait to see them perform this Tuesday at Queer Comedy at Zanies presented by Adam Guerino’s Outloud Chicago.

Carey Callahan performed all over the Midwest at places such as The Cleveland Comedy Festival, The Grog Shop, The Beachland Ballroom, Zanie’s, Chicago’s Mayne Stage, Chicago Underground Comedy and the Ohio Lesbian Festival. They also host the weekly podcast “The Awkward Sex Show” and are currently studying to be a Family and Marriage Therapist.

The L Stop: Carey, I hate to ask this right off the bat, but I want to make sure I’m up to par with the terminology and be all politically correct….is it standup “comic” or “comedian”?

C: I love this. Let’s see, so comedian is supposedly not gender neutral, we have “comedians” and” comediennes” and never the two shall meet. If I’m gonna be consistent in my gender neutrality, if iIm going for Switzerland levels of being neutral, gotta go for “comic.” Also I think “standup comic” flows better than “standup comedian.”

TLS: When and why did you decide to start doing stand-up?

C: It was less a decision made out of free will and more of a mermaid/sailor relationship. I kept trying to steer the boat to other occupational shores and the sweet mermaid song of getting to talk into a mic with a light on me kept pulling me back out to sea. I went to law school for a year, I tried to be a union organizer. I’m still trying to be a therapist- standup always pulls me back! The thing about standup is the more I do it the quicker I learn everything important about myself, and that’s really hard to walk away from. I’ve quit and relapsed 5 times since I started at 24, and I’m only 30. Now that I have the Awkward Sex Show Podcast, where on a weekly basis I get to hear real awkward sex stories and have the hilarious Ramon Rivas crack jokes with me, I’ve thrown in the towel, the comedy sea is my home now.

TLS: Where do you draw your material from?

C: If I can’t stop thinking about something, whether that’s a weird thing some guy on the bus said to me or how my body is changing on hormones or whether I should start The Church of Frank Ocean, that’s what I need to be talking about onstage. It’s the best thing to do with my obsessive thought patterns.

TLS: How has transitioning influenced your material?

C: I just recycle Andrew Dice Clay bits now, in between tearing phone books in half. Taking hormones to affirm my gender and being out as trans has made me way more relaxed in general, and being relaxed is awesome for jokes. I’m still talking about the same old ‘ish I have always talked about- the rules and regulations put forth by the Gender Bureau and how we navigate them. But DAMN it is nice to be talking about that stuff while presenting myself as a gender that feels natural and easy to me.

TLS: What kind of response or reaction have you gotten from your regular fans after your transitioning?

C: My fans are the raddest people ever made in human history, so across the board they’ve been like, “Congratulations! Awesome! Are you going to throw a party?” This is absolutely the correct reaction to a person announcing they’re going to transition. Congratulate them, get yourself an evite, ask what stores their gift registry is at. (, thanks for asking…I especially need a swimsuit).

TLS: Do you feel that being trans offers you an advantage in any way? (as a comic and/or in general)

C: For sure. One, I have a built in excuse to pursue friendship with other trans people, and trans people tend to be geniuses, so that’s pretty sweet. Two, there’s something to be said for the relief of moving from less comfortable to more comfortable in how I present myself to the world- it’s true what posters with sunsets on them say about an Attitude of Gratitude. I’m having a ball feeling grateful. Also, it is so FASCINATING to go through seeing how hormones affect my body and mind, and how people treat me differently. I recommend being trans wholeheartedly, two thumbs up, talk to your doctor today.

TLS: What challenges, if any, do you face as a trans in a field that is hetero male dominated?

C: Comedy is a grind for everyone, even for ironically racist/sexist/homophobic/generally dick-ish straight white cis guys, aka IRSHDSWCG’s. If you are not straight, not white, not cis, not a guy, or just not a dick the grind can feel more frustrating because you might want to punch some IRSHDSWCG’s in their faces sometimes. HOWEVER, anything you can do to create a daily life that makes you happy will help you resist those punching urges and keep you on your grind. You just have to remain connected to why you enjoy comedy. If you’re looking for some attention that your parents failed to provide in childhood, go get it! You deserve it! And don’t let the ironic racists slow you down!

TLS: Who are some of your comedy idols?

C: Big names whose comedy I love include Dave Chappelle, Wanda Sykes, Katt Williams, Maria Bamford, Hannibal Buress, Dan Telfer, and I’ll always have a thing for Bob Newhart. I like a lot of different styles of standup as long as you’re a total genius at it. But the people who REALLY are my heroes are the people I’ve seen take the challenge of being “different” from the comedy mainstream and create their own spaces and audience for that. That’s what Adam Guerino has done with Queer Comedy at Zanies. He took the experience of being a gay comedian, which can be really hard in some mainstream venues, and decided to create a show that connects queer comics with a welcoming audience. Transforming a challenge into an opportunity for yourself and others is so BALLER.

TLS: Who are some of your trans idols/mentors?

C: I idolize almost every trans person I meet, but specifically Our Lady J’s music means a lot to me. I saw her show “Beauty as Goddess” and came away thinking, oh, you can do and be anything you want as long as you’re an artistic genius while you do it. As far as mentors….I don’t have one but it seems like a really hot idea especially if the mentor/mentee relationship had a kind of daddy/houseboy vibe to it. Any mentors with substantial financial resources should send me an email.

TLS: What do you enjoy about performing for queer audiences?

C: Queer people are smarter and cuter than muggles, and they have more interesting thoughts to share after shows. And they’re so much more generous with buying me drinks. I honestly feel bad for straight comedians that they don’t get as many queer gigs.

TLS: Do you feel a sense of obligation to educate the general public on the issues facing the trans or LGBTQ community as a whole? Or to promote awareness and acceptance?

C: That sounds hard, and I’m only a fan of hardness in very specific contexts. I’d rather just be me and tell the jokes that come out of my weird head, and find audiences who those jokes do a little something for. Don’t get me wrong, when I look at the work projects like those the Sylvia Rivera Law Project and TGI Justice are doing, I know trans people are going to save the world. But this particular trans person is going to tell jokes about sex parties and having a Catholic mom while the world gets saved. It’s more my skill set.

Catch Carey Callahan this Tuesday, January 29th 8:30 p.m. at the Season 3 opener of Queer Comedy at Zanies presented by Outloud Chicago with headliner Liza Treyger hosted by Adam Guerino, also featuring Ali Clayton and Archer Coe. Tickets are $10 advanced or $15 at the door. Click here to purchase tickets!

Outloud Chicago is a series created by Adam Guerino to bring queer entertainment to mainstream Chicago venues.

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About Alma

A Chicago original of Mexican decent, Alma has been part of the Chicago’s LGBTQ community longer than she’d like to admit. She’s been maneuvering through its diverse social circles, networking relentlessly in an attempt to satisfy her need to understand and get to know the people that make up our amazing and unique community. Her path began as a social butterfly whose interests were solely to meet and entertain friends. Now her desire is to channel her strengths, talents and passion into ways she can be of service for the Chicago LGBTQ community that she so loves and respects.


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