Meet Penny Oswin of The Sunday Funday Fabulous Open Mic

Penny Oswin hosts The Sunday Funday Fabulous Open Mic every week at Jacques Cabaret in Boston.

By Katie Conway, Contributor

If you’re like any of us here at WICF, you’re probably still missing that wonderful time of year where we celebrate women in the comedy industry and showcase their awesome talents at our annual Women in Comedy Festival. But wait a minute – did you know there are even more fantastic places around Boston that have up-and-coming open mics and comedy shows run by and starring women? Yes, you heard that right! And WICF Daily got the chance to interview three of these amazing female showrunners – who they are, what their shows are about, and some advice for anyone else trying to break into the comedy industry.

Here to talk about her start on the comedy scene, the Nicholas Cage baby meme, and her brand new show The Sunday Funday Fabulous Open Mic at Jacques Cabaret is the fantastic Penny Oswin!

Tell us a little about yourself! Where are you from? How did you get started in comedy?

I’m from NYC (everyone goes silent when I say that). I was born in Queens, grew up on the Gold Coast of CT (still very close to NYC ) and lived in NYC for six years before moving to Boston in September 2015. I went to art school in NYC and realized my life in the city wasn’t working out, so I moved to Boston.

When I was younger I did theatre classes pretty sporadically and always looked up to comedians as my idols. So when I was 13 and 14, I did some stand up comedy classes. When I was 21, I went to my first open mic. My friends kept telling me I was funny and should do stand up blah blah blah. The story of how I went to my first open mic is bizarre but funny . I was running an errand and all of the sudden there was a strange man outside my apartment like, “Excuse me, miss” and whenever you hear those words in NYC from a strange man nothing good ever happens. So I decided to walk in the other direction and the man yelled at me “YOU LITTLE BITCH – YOU RUNNIN’ HUH?” I ran for my life and wound up at the People’s Improv Theatre (The PIT) which was right around the corner from my apartment. Turned out there was an open mic that night so I was like fuck it, I’ll go up. The show was Vicious Cycle and it was a lottery-style open mic where everyone got 2 minutes. So I got up and told a story for 2 minutes and I did alright for my first time and have been addicted to stand up since.

Who are some of your comedic inspirations?

I’d say my favorite stand up comics are Jim Gaffigan, Robin Williams, Eddie Izzard, Aziz Ansari and John Mulaney. I grew up watching Seinfeld, which has been a big part of my life as well. However, I’ve been inspired by several female comedic actors like Tina Fey, Amy Poehler, and Rachel Dratch – I’ve always loved SNL and being on SNL is my main goal as a comedian. I’m also a huge fan of British humor TV shows like Monty Python, The IT Crowd, Little Britain, The Catherine Tate Show, Peep Show and The Inbetweeners, which is where I get a lot of my dry wit and inspiration to play characters.

I understand you run The Sunday Funday Fabulous Open Mic at Jacques Cabaret in downtown Boston. Can you tell us a little more about that? What are some of the daily tasks of a comedy showrunner? How does someone become involved in this show?

I wanted to have a Sunday mic still go on now that Iron Furnace is no longer with us and wanted a mic that everybody can get to via public transportation. Jacques is in the perfect venue because it’s located conveniently off all Green Line and Orange Line trains. Being a huge fan of drag queens, I would always go there for drag shows which were the best time and I want to bring that energy to an open mic. The great thing about this mic is that it starts at a convenient time that does not overlap with other mics, and comics that still want to do another set can go to Midway Cafe in Jamaica Plain right afterwards very easily off the Orange Line.

One can become involved in the show in various ways. If you are a female comic, you have the opportunity to co-host with me as long as I book you in advance to do so, as I would like to have rotating female hosts. If a male wants to co-host with me, he will have to dress in drag. However, any comic can sign up and go up at the mic. I also book three features and any male feature has the option to dress in drag (I highly encourage it for entertainment purposes). This is Jacques – go hard or go home!

I already run my own monthly show called Penny 4 Ya Thoughts? at Arts at the Armory which is a dating-themed comedy show where 13 comedians tell 5-minute bad dating stories. In the middle of the show is the Tinder roast, where I go through 2 comedians’ Tinder profiles and have the audience help swipe left and swipe right on potential matches. If they get a match, then the comedian has to message them on stage.

The hardest part about being a showrunner is the marketing aspect. Most importantly, you need to draw audience and keep the audience’s attention throughout the show. A lot of the pre-show marketing is just as much work as hosting because you need to have people come to your show. You need to make sure to have fliers, Facebook ads, promote like crazy on social media, etc. Competition is tough but necessary in entertainment when you have shows going on in other places – you have to make sure that people come to YOUR show versus others that are going on.

Sometimes as a host, jokes can hit or miss very easily, but the good news is that sometimes the performers can pick up after you. The opposite scenario can happen where the performer bombs and you have to pick up after them. So you really have to be prepared for any scenario. And most important is to keep up the energy and listen to everyone’s set to feed off of what their set was about.

Any really funny/inspiring/horrifying stories you can give us from Sunday Funday or previous shows you’ve worked and/or performed in?

I can tell you two of the funniest moments happened at Penny 4 Ya Thoughts:

One story was back in January when I was doing the Tinder roast with Shawn Carter and Anthony Massa where the subject of Nicholas Cage baby was brought up (it is a terrifying meme). Anthony got a match and we asked what we should message his match and a fellow comic, Sami Anderson, shouted “Nic Cage baby!” And Anthony actually sent this girl on Tinder a picture of Nicholas Cage baby and the reaction was priceless because the girl on Tinder was freaked out. This all happened live on stage and it made the show great.

When I did the Tinder roast with Tricia Auld, it was fantastic. Stephen McConnon then got on stage to join without any shame and then Tyrone Jones walked on stage just to look at the Tinder profiles. The whole thing just became a free-for-all. But anything Tricia does is freaking hilarious and she has no shame whatsoever, so it made the Tinder roast one of the best moments.

What are some of the challenges you face as a comedian? What are some of the rewards?

Being a comedian is fun, rewarding and tough. I keep my work life separate from my comedy life, which is nice. However, balancing my comedy life and my non-comedy life can be a challenge. I prioritize comedy over almost everything else and that can lead to burnout at times and being distant from friends and family. As much as I feel like the Energizer Bunny and can keep going, I need to remind myself that I need to pace myself and take time to chill for a bit.

Of course, being a woman is tough especially in comedy. Not only is there a ridiculous amount of sexism when you tell non-comedians (non-coms) that you’re a comic but people also expect you to be “on” all the time. It really irks me when I go to family functions and people are like, “Can you perform your routine for us?” or even hanging out with friends’ friends who aren’t comics that are like “Tell us a joke” – I spend so much time on stage, can’t I just chill for once?

The most rewarding thing about comedy is feeling energized after a great set because you know that you made people laugh, which is the hardest thing to do. It’s also rewarding to know that people actually understand you and like you when you know you’ve been bullied and not accepted most of your life. Being on stage is like an escape from reality not only for the audience, but for the performers as well.

WICF is an organization that stands for creating more opportunities for women in a field that has often been predominantly male. Do you have any advice for other women who are considering a career in comedy?

I’d say go for it. Yes, stand up is predominantly male, but that’s just noise that you need to block out. Remember to keep your day job while you do it because the beginning stages are not lucrative and it will take a while to monetize comedy. It’s going to be rough the first few times you do it but don’t be scared. Just do it and keep going.

Tell us a joke!

Ever have sex and think, “This would be way more fun by myself”?

Give us the inside scoop: any comedians on the rise you think we should be on the lookout for?

Oh man, I have so many friends that are fantastic and hilarious. But I can tell you a few female comics in the scene that I admire – Nichole Auclair (she does more Providence shows but she’s brilliant), Tricia Auld, Ellen Sugarman, Srilatha Rajamani and Nonye Brown-West. I can list so many other comics right now but it would be the longest list ever.

Any other advice you can give to aspiring comedians in the Boston area? How can they stand out? How can they improve upon their craft?

One of the most important things to do as a comic is be nice and trustworthy. If you’re a diva or just difficult to work with and burn bridges, you’re going to get booked less. Bookers like to work with comics who are reliable because if you keep flaking out, you’re going to lessen your chances of getting re-booked on that show.

If you want to stand out, don’t copy other people’s jokes and be confident. Confidence sells and when you’re comfortable with yourself, so is the audience.

Taking improv classes helps you think on your feet and not overthink everything you’re going to say or do on stage so I recommend maybe taking a few classes just to let your brain go and loosen up on stage.

If you want to improve your craft, you must keep writing and going to mics as much as you can. The more you show up at mics, the better you get. It’s basically like going to the gym. And don’t be afraid to ask your peers for help in creating a joke because they are more than happy to help you.

Where can fans of yours see you perform? Where can they follow you on social media?

I’m usually at The Comedy Studio, ImprovBoston or other local shows or mics.

Social Media:


Twitter: @pennyoswin

Instagram: @pennyoswin

Snapchat: @pennyoswin

Aside from comedy, do you have any other hobbies/interests/a super secret double life?

Cooking, eating and napping are my favorite hobbies when I’m not on stage. I feel like I’m so consumed with comedy that it’s basically my life and don’t know what to do with myself when I’m not at a mic or show.

Usually when I’m not on stage I’m pretty domestic – cooking and cleaning are my main priorities. I’m pretty introverted, so I need a lot of downtime to mentally cleanse before going out again. I’m really into meditation as it truly does cleanse the mind. Walking around while listening to music also does wonders for me mentally as well.

Final Question: What color is your aura? Please elaborate.

My aura is allegedly yellow, which is ironic because of how dark my wardrobe is. Anyway, someone did “see” my aura and said it was yellow because I exude a lot of positive energy, kindness, passion and confidence.