Making folks laugh from both live standup stages and social media feeds — all while looking great in leather pants — Jack Sullivan is New York’s queer comedy star of the moment.
Thotyssey: Hi Jack, thanks for talking to us today! So, we’re having an almost nationwide Snow Day… do you like a chance to hole down and be cozy, or do you get restless when you’re not out and about?
Jack Sullivan: Hey there… thank you! So I am actually down in Miami; I came down a few days ago to do a show, and am now blessed to be stuck here for another three days. I definitely get restless… I am always go go go, so when it’s impossible to do anything, I don’t love it.
That’s great you’re in a warm place! As a standup who does a lot of touring and traveling, do you have a favorite city outside of NYC?
I love the sun and warmth and the beach, so I love Miami, LA, and San Diego. I’m half Cuban, so I’m warm blooded. NYC is definitely my favorite city in the world, though.
Is New York your original hometown?
No, I was born and raised in Washington DC and the DMV. I will always have so much love for the area, but NYC is home. I’ve been in NYC for eight years now… so two more, and I’ll be a New Yorker!
Were you always considered a funny kid / person growing up? And what people, shows, etc. did you find funny?
I was definitely more of a class clown, but I was pretty shy and reserved growing up. I was very closeted and insecure. In high school I started to come out of my shell, and in college I really did before coming out after I graduated.
Man, growing up in the 90’s/2000’s… we were so blessed. The era of Will Farrell / Molly Shannon / Tina Fey / Amy Poehler / Kristin Wiig (LOVE Bridesmaids). And I loved (and still love) Katt Williams — he’s hysterical. And Mo’Nique.
That was truly a great time for comedy! How and when did you start doing standup? To me, that just seems like the most difficult of all the performing arts as far as overcoming nerves, staying on course, reading the room, selecting the right wording… everything!
Honestly I could never have done it if I hadn’t gotten sober. I started 3.5 years ago because I had always wanted to perform and do something creative, and my friend Austin get into it and saw how accessible it was. So I went to an open mic and just talked for five minutes, and instantly was hooked. I haven’t looked back since!
What’s your favorite part about doing standup?
It’s so challenging. You’re constantly stimulated, and you have to keep writing and keep improving. And it has a way of consistently humbling you, which I think is good for me. The highs and lows keep you hooked! And I love connecting with people of all different backgrounds at shows. Overall, I really love what I do.
Social media has become vital to the success of today’s standup scene, and going viral / having a large following can make a huge difference in someone’s career. You certainly have maintained a string, constant presence online. Is that a huge pain in the ass to constantly manage, or is it fun to make content?
100% of both. I love connecting with people from all over the world and engaging with them to learn about where they’re from, and how they relate to different pieces of content. And at the end of the day, I have a platform and all these solo shows because of social media… so I am super super grateful for it. It’s time consuming for sure, but ultimately it’s why I’m here.
Is it a challenge to navigate where to perform and who your audiences are as a queer comic?
From a social media perspective, [my audience is] definitely gay men. My following is 97% men on Instagram, so I am looking to cross over and appeal more to women there. But on stage, I find I do best with straights. They get a kick out of me, and I think they enjoy hearing a different perspective.
I remember when they used to say that you can’t be hot and funny, but we definitely see that that’s no longer true these days! Do you think that looks play a role in standup?
The looks question is a very, very tough one. How I dress is obviously a conscious choice — with the leather pants, given how I’ve been embraced by the leather community. I often worry about looking like a gimmick to straight white bookers, but I prefer to do what I want than to dress how others want me to. And I think these days, audiences will laugh if it’s funny… and that’s all the at matters.
Is dating difficult when you’re a standup? There’s practical stuff to consider like being on the road a lot and keeping weird hours… but also maybe hurt feelings about jokes, jealousy, intimidation, etc.
Datings difficult mainly cuz I don’t have a lot of time – but yes, people are often cautious about ending up in jokes.
You’ve got some stuff coming up! You’re featured in a New York Queer Comedy Festival showcase at the Greenwich Village Comedy Club on February 11.
Well, this one is extra special to me… it’s my first time co-producing with the founder of the festival, Drew Tessier, since 2023! And it will also be my first time doing 20 to 25 minutes at Greenwich Village Comedy Club, one of my home clubs where I first started. The lineup’s great, and I’m so excited to headline and do a long set (thank you, Drew). And it’s all new material from what people saw me do in years past.
Looking ahead to April 25, you’ll be starring in a solo showcase at the Laurie Beechman Theatre: The Perfect Date!
Yes! I’m doing a full hour on the night of my 35th birthday – Saturday, April 25! I’m so excited for everyone to see my feature length set, and to celebrate with all my friends, family and supporters. The title is, of course, a reference to the line in Miss Congeniality on April 25, because, well… I am gay.
What else is coming up for you?
On Thursday, September 9th I’ll be doing an hour at Broadway Comedy Club. So stay tuned for details!
Excellent! Finally: what is a pet peeve of yours?
Honestly, slow walkers in New York. Tourists and straight people love to spread out and walk in large groups on the side walk at a glacial pace… and it kills me.
OMG, same! Thanks, Jack!
Check Thotyssey’s calendar for Jack Sullivan’s upcoming appearances, and follow him on Instagram, TikTok, YouTube and LinkTree.
Thotyssey 