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Comedienne of the Cabaret: 10 Questions with Penny Oswin

Interview by Sarah Belclaire Photographs by Sarah Belclaire

Shortly after making the move from the fast-paced comedy scene of New York City to the more close-knit Boston, Penny Oswin found a new identity, a new home, and a new gig hosting the live dating-themed comedy show "Penny 4 Ya Thoughts." Penny and I crossed paths in 2016 and bonded over David Bowie, Prince, and a love for travel, fashion, and show business. An old soul in a provocatively fresh act, Penny is almost too New York for its quieter, more conservative sister city. But, she's determined to inject a confident female voice into her new hometown.

Sarah Belclaire (SB): Women in comedy are making some well deserved noise these days. Sarah Silverman, Amy Schumer, Tiffany Haddish. Where do you feel you fit into this new wave of comediennes?

Penny Oswin (PO): Well, these women are bold and taking strides to be the voices that most women are afraid to be. There’s still this old-fashioned stereotype going around that women have to be mild-mannered, submissive, and of course the classic, that women aren’t funny. I definitely fit into this category of women who are saying “Fuck those stereotypes.” We’re all here to do the same thing as these men — make people laugh and say "Yes, women are funny." I don’t want gender to play into just being funny. All I care about at the end of the day is doing my thing and making people laugh. That’s it. Then I can go home happy and eat tacos without pants on and remind myself, “Yes, I am a badass lady doing badass things”.

SB: You are an astute creator of stage personas. Which is your favorite to portray?

PO: Oh man, being a character actor is so much fun. I’d say Geraldine Ellis, the Back Bay socialite, is the most fun to portray. She is a crazy-rich alcoholic woman who has had 10 husbands and makes money...marrying all of the wealthiest men in the Back Bay. The best part is not just using the affected, Trans-Atlantic, rich-person accent — but dressing to the nines. Her voice is a combination of Cruella De Vil [and] Audrey Hepburn, so of course the outfits have to match, like Audrey Hepburn-meets-Jackie O-meets-Joan Crawford realness.

SB: How does being a New Yorker factor into your comedy?

PO: It’s certainly made me have thicker skin and no filter. NYC is a very tough place to start out because everyone is super competitive and wants the same thing as you do, so they will cut their way to the top. Boston is competitive in a different’s such a tight-knit wolf pack that [you've] gotta find your way in there. And once you’re in there you’re in for life (if you don’t fuck it up).

But growing up in a very NYC-Jewish household, there is certainly some Larry David type comedic influence as I grew up religiously watching Seinfeld. Growing up in a neurotic family and having wacky experiences and stories from living in NYC has definitely helped me develop more material.

SB: What's the best and worst gig you've ever done?

PO: The best gig I did was at Dangerfield’s in NYC. I remember the crowd laughing so hard and having several applause breaks...I felt like I was on Cloud Nine. And the other times I’ve been back I had the same responses...It’s super rewarding when the audience is having just as much fun as you are on stage.

The worst? I did a drag queen open mic at Jacques' Cabaret and they asked me to do stand-up comedy after all these drag queens were being super fabulous and fierce on stage. Man, was that a hard act to follow. I tried doing my routine — nobody was paying attention. The audience was heckling me. And then one woman just shout[ed] in the middle [of my set]: “GO TO SLEEP!” I was supposed to do about seven minutes of material, and I had to cut it short because I really couldn’t even get the audience’s attention...The drag queen hosting the show came on stage with me just to try and clear things up. It was a hot mess, but now I have a joke out of it.

Penny as Geraldine Ellis

SB: How would you describe your comedy show Penny 4 Ya Thoughts? What made you want to create this show?

PO: “Penny 4 Ya Thoughts” is a dating comedy storytelling show where 8-10 comics come up on stage and share their worst dating stories, and if they blank out, they can just do their normal stand-up routine. In the middle of the show I have a “Tinder Roast," where I have a comic and an audience member come up on stage and we help them find matches with audience participation. I also give out two lottery spots to audience members and comics to share their worst dating stories.

I created this show because — One — I wasn’t getting booked as much [as in the past] because I was so new to the Boston comedy circuit and — Two — I wanted to share my encyclopedia of bad dating stories...Right after I pitched the show I [broke up] with my boyfriend...shows how great I am at relationships...Fast forward to November 2016, I did the show [in someone's dank basement in Allston], and it was a hit. The room was so packed that I called up Arts at the Armory (a community arts space in Somerville, Massachusetts) the next day asking for a December date, and they gladly gave it to me the day before New Years Eve. It was a success despite being around the holidays, so I had a residency at Arts at the Armory from Dec 2016 - August 2017. I moved the show to Jacques' Cabaret along with my new open mic, “The Sunday Funday Open Mic,” so now “Penny 4 Ya Thoughts” has its residency every third Friday of the month.

SB: Are your friends funny people? Do you find you need to surround yourself with others who have a similar sense of humor? Or people who inspire you? PO: Most of my friends are comedians, so they are funny people. However, I have non-com (non-comedian) friends, and we do have a lot of funny moments together. I mean, comedians don’t always have to be completely on all the time, which is a big misconception among people who don’t perform comedy. I try to surround my self with people who would bring me up, not down, because it’s obviously healthier. However, I [also] like to surround myself with people who get my sense of humor because not [everyone] does. Not even my parents. But the people who inspire me and who I look up to aren’t all stand-up comics. Most of my influences are comic actors and drag queens.

SB: For you, what's the most important way to push boundaries as a female comedian? How do you break into that predominantly Male space and kick ass while doing it?

PO: First of all, it’s okay to be dirty, but when you go completely overboard and your entire set is just gross for shock value, then you lose the audience’s interest. Take, for example, Amy Schumer’s most recent Netflix special. [It] was just too much gross and not as much actual joke-writing [or] well-constructed humor. I think when women show they own the stage and are confident, that’s the best way to push the boundaries. As I stated earlier, it goes along with the age-old stereotype of women not being funny. Once a woman is as cool and confident as their male counterparts on stage, then it really is pushing the boundaries. I never really saw gender when doing comedy, and I don’t want it to be about gender. Yes, usually I’m one of the few females in the room and sometimes the only one. However, the way I kick ass is just by going up there and doing my thing. As drag queen Bebe Zahara Benet always says, “Another day, another slay."

SB: Why Boston? How is the comedy scene there different from New York?

PO: When I was living in NYC, I was super young and I don’t think I had the maturity to deal with pursuing comedy in NYC. I didn’t know the right people — I only knew those who did the bringer shows. I was good when I started out but unfortunately had to put comedy on pause for a bit to finish school and figure shit out after I graduated. I moved to Boston eventually to really jump start my life and figure myself out. I fell back into the comedy scene in Boston because I thought it would be more approachable and more opportunities that weren’t as cut-throat in NYC. The Boston scene is a lot more tight-knit, more like one big family rather than NYC. As I mentioned earlier, the Boston comedy scene is one big wolf pack and it takes time to just break in and be accepted. It’s a bit cliquey, but eventually you find your people. NYC is more like pay-to- play open mics and just extremely competitive. A lot of the shows in NYC are bringer shows whereas Boston isn’t like that. Most of the shows are at bars/restaurants, so the venues make money off of what the patrons buy. However, a lot of the NYC venues are strictly comedy venues, so they need to make money off of the performers bringing people along with the two drink minimum per person - it’s how they keep the roof over their head and the lights on. Bringer shows are frustrating and gets expensive to your peers as well! In Boston, it’s easier to perform on shows because you don’t have to go through the hassle of bringing people. But Boston does breed some of the best comedians in the business (Sarah Silverman, Bill Burr, Conan O’Brien, Joe List, Myq Kaplan - to name a few) and once they are polished after basically being incubated here, they move on to LA or NYC and become famous and live happily ever after

SB: Being in the performing arts can be a struggle. How do you keep going and stay positive about it? What are some challenges you have faced or overcome?

PO: I always tell myself that the most important thing is to just show up. I usually have to remind myself on bad days that I’m going to feel so much better just performing on stage and being there, because it’s true. One thing that is challenging is that it’s easy to get into your own head. A lot. It’s a frequent struggle, especially when you are a competitive person and see your peers doing so many shows that you don’t get booked on or haven’t gotten booked on yet. So it’s a lot of this inner dialogue like, “Am I even good enough? What do they have that I’m lacking? Am I actually funny?!” Self-doubt comes in a lot of the time and then the head can easily spiral down the rabbit hole. I guess the only way to overcome that is to keep going and showing up because if your head wins, then you just miss out on life and opportunities.

Another struggle being a very blue — show biz term for “dirty” — female comic is that men sometimes think they can hit on me and be aggressive [just] because I would make all these dick jokes. No, it isn’t a free pass for you to do that. It’s just part of an act and it stays on the stage. Dating is a big challenge as a comedian because every one of your potential partners think they’re going to be material and basically walk on eggshells because of that. If I’m genuinely interested in someone, I am not going to talk about the relationship on stage because that stays private. If you do something to me that has hurt me or just was a weird experience overall, of course I’m going to talk about it. Personal lives in general are tough. Ditching family or friends’ events because you’re booked on a comedy show... A lot of sacrifices for the stage but eventually, the ones who love you and get you understand. Most of the time.

SB: How do you feel about having your picture taken?

PO: I love it. I’m a comedian — I live for the applause, applause, applause [starts singing Lady GaGa]. All kidding aside, I really love being in front of the camera and stage so I love hamming it up.

Check out Penny on Instagram and Twitter at @PennyOswin and Facebook at @Penny4YaThoughts.


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