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Meet Jay Hollingsworth of Big Irish Jay

Today we’d like to introduce you to Jay Hollingsworth.

Thanks for sharing your story with us Jay. So, let’s start at the beginning, and we can move on from there.
In 2008, I was living in Boston working as a Director of Technical Support for an online data storage company. I had thought about doing stand-up for years, even going as far as to write premises, but I just never had the balls to go up and do it. I had asked a girl out on a date, and she let me know she couldn’t go out on Wednesday night because she had “comedy class.” I asked “what’s that? Where do you do that?” and she directed me to the Boston Center for Adult Education.

The BCAE had various classes from Improv (which she was taking), cooking, pottery, and various other classes and then I saw “stand-up comedy” taught by Dana Jay Bein. I thought “I’ve been wanting to do this for a while, fuck it, I’m going to sign up.”

I completed the class and asked the instructor if there was a show or open mic I could do because I didn’t care about the graduation show. When you take comedy classes, you always have a final graduation show, everyone invites their friends and family, and everyone does great since everyone’s support systems are there. I didn’t want that. I wanted to go up in front of a group of people that didn’t know me and either get laughs or bomb, but earn whichever I earned.

That first show I ever went up was at Kennedy’s Midtown in Boston hosted by Scotty Lombardo, and it wasn’t an open mic, but rather a showcase shows that I had no business being on. On this show were veteran comics such as Shane Moss, Myq Kaplan, Dan Crohn, Tyler Boeh, and some other great comics. I did 8 min’s of awful stand-up, got a few laughs and was paid my first time doing stand-up. I didn’t feel I deserved the 20 dollars I received so bought the other comedians pitchers of beers.

From that first time on stage, I was hooked. A lot of comics talk about their first time and say “I got that laugh, and I was hooked…” for me it wasn’t that. I’ve been making people laugh my whole life. Going to 13 different schools growing up, you gotta learn to be entertaining as the new kid. For me, stand-up has always been about the science of comedy.

That first time on stage, the moment I got off stage, I immediately was going over my set, thinking “why didn’t they laugh at this? Why did they laugh at this part? I should’ve said this when that guy in the audience made that comment…” I love jokes and figuring out new jokes and premises. You’ll get an idea for a joke, and you’ll KNOW it’s funny. You go up and tell it, and it gets NOTHING. You keep trying, and it gets nothing, but in your soul you know there’s funny somewhere in this joke.

Then, one night you’re working on the joke, and you change one word, or a voice inflection or you rearrange it, and it works! That is what I’ve loved about stand-up from that first night till today. In 2009, I was laid off from my day job in Boston and had to figure out what I was going to do. My friend in Seattle let me know he had a room he could rent out to me for $500.00 a month flat and I decided to jump on it.

I was collecting $650.00 a week in unemployment and moved to Seattle and did nothing but stand-up. Hitting as many mics as I could a night, every night. I had the mentality that some people may think I’m funny, some won’t, I can’t control that. All I can control is how hard I work, and I don’t want anyone to outwork me. So that’s what I did, I worked my ass off in trying to get better.

Around 2011, I was approached by the manager of the Parlor Live Comedy Club in Bellevue, WA to see if I would be their club’s house emcee. This gave me an opportunity for a steady income from comedy as well as five sold-out shows a week to perform while working with the best comedians in the world. I jumped at the opportunity with the stipulation that I could still do other shows during the week and I could go on the road when opportunities came up.

Even though this was a huge opportunity and a steady gig, I didn’t want to rest. I wanted to keep grinding, staying hungry, always improving. In 2014, I moved to Los Angeles. I chose LA over NY because of the connections I made as a house emcee, most of those comedians lived in LA. I figured it’d be better for me with most of my relationships here in LA.

Since moving to LA, I’ve written for game shows, been viewed over 80 million times on YouTube for various sketches, stand-up clips, done some commercials. Got a part on a major sitcom where I played a gay love interest that included a kissing scene, only to have my scene cut. It’s been great. All while touring headlining clubs throughout North America.

Overall, has it been relatively smooth? If not, what were some of the struggles along the way?
I’d say the biggest struggle for me with being a stand-up is having lived most my life in the corporate America world, I still sometimes struggle with pay in comedy. When you work a 9-5 you have sick days where you still get paid, you have two weeks paid vacation, you have health benefits, you also know you could go into work, have an off day or slack, or you could have the greatest day ever, but you know that check every two weeks is going to be a certain amount and you can budget accordingly.

In stand-up, unless you have a writing gig or on a show, you have to be REALLY smart about your money and budgeting. You may have a month let’s say from touring and merch you make $8,000. You’re good, you’re paying your bills, eating, everything’s great. Then the following month, for whatever reason you have no dates on the books.

You may have the month after filled up and good, but this next month, nothing. You now have to adjust and also hustle to try and pick up gigs in that off month. This job is definitely not for someone that isn’t a hustler. You gotta be hungry and work your ass off and never let up. The other difficult part of being a comic is there’s no career path, meaning if you work in Corporate America, you know that if you do certain things in your current position you can get bonuses and promotions, and you have an idea of what steps to take to move up the corporate ladder.

In comedy, no path is the same. Nobody can say “do these five things, and then you’ll get what you want.” You could even do the exact same path as someone else, and it won’t work the same. That’s probably the most frustrating thing for me. I don’t have a manager or agent, so opportunities will come and go that I never even knew or heard about. I always try and just keep working hard and improving as a comedian. That’s one of the only things I can control in this industry.

Alright – so let’s talk business. Tell us about Big Irish Jay – what should we know?
My stand-up style is I’m a storyteller. I always say with my comedy that everything I say on stage is either something that happened to me or something I believe strongly in. I have a very conversational style, and many people have described my style as if you’re sitting at a bar having a beer with your funny buddy.

The things I’m most proud of up to this point in my career is I was a finalist in the Bay Area Black Comedy Competition where I was the only white guy in the finals that year. I won the March Comedy Madness Competition here in Los Angeles beating out over 100 comedians here in LA, and I’d say I’m proud that I’m respected by my fellow comedians.

Any shoutouts? Who else deserves credit in this story – who has played a meaningful role?
There’s a ton of people that have helped me along with my career. From Dana Jay Bein who’s stand-up class, I took, to Scotty Lombardo the first guy to ever give me time and has let me stay at his place multiple times when I come back to Boston for shows.

The Parlor Live for giving me the opportunity to be the house emcee for three years. My buddy Kane Holloway who I grinded mics with from the days in Seattle to now in Los Angeles.

The Broken Drift production company who’s currently filming a docu-series on me and believing my story is interesting enough.

Doug Benson was the first headliner to take me on the road with him. Alonzo Bodden has been unbelievably helpful from taking me on the road with him, to advice, to help me navigate LA. Joey Medina and Jon Reep are both friends that have given me work and advice.

KevOnStage I’ve known for about ten years going back to Seattle and when he moved here to LA things really blew up for him, and he’s always hit me up for writing, sketches, stand-up, and other opportunities.

There’s literally 100’s of comedians that have vouched for me, introduced me to bookers, given me gigs, let me crash on their couches, beds, floors.

Club owners and managers that are not just “club bookers’ but I have actual friendships with from Ryan Cott and John Tobin in Boston to Casey Currier in Phoenix to Jennifer Canfield at Laughs Unlimited in Sacramento to the whole Norwest family at the Tacoma, Spokane and Skyline Comedy Clubs. They’re the best.

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