The Young Hustle’s Goal Is To Be The Best Comedy Show and Comedians in Chicago


Introduce yourself

What’s going on, we are The Young Hustle, and our names are, St. James Jackson, aka Mr. Show business, aka Chocolate Thunder, Nick Ogle. I am 24 years old and started comedy in August 2016, Clay Hurlburt. I am 23. September of 2015 is when I started comedy, and last but not least, I’m Skyler Higley. I am 22 and started in September of 2016.

Clay and St. James I know you are the creators of the show, how did you guys come together to start the group?

St. James: I was at an open mic, I had a great set and was about 20ish. I met this lady after the show and we went to The Annoyance Theatre for another open mic where she then met Clay. We were both getting the same vibes from the girl so we kind of butted heads because we were both trying to get this girl. When we took her out of the picture, we became best friends.

Clay: She is still a big fan of the show. She loves the show. We were young and we both were awesome. We were all like 20, 21 and the comedy scene was way older back then, like its gotten way younger in the past couple of years. So it was just natural when you are with someone else younger doing comedy. Like any great relationship, it has gotten better as the years go on.

St. James: I was turning 20 and I told Clay, “You know what would be great to celebrate my 20th Birthday?” Let’s have a show, so we did.

How did you get your show’s name and what does it mean to you?

Clay came up with the name but we spitball for a while. When we started, as we stated earlier, we were the only 20-year-olds running the comedy scene and we had the mentality that we were gonna outwork everyone. We wanted a name that painted a picture in your mind. “The Young Hustle,” you just feel that it’s different from all other names and reminds us of nothing else. That’s how dope it is. It captures everything in three words. It is a story and that is who we are.

Nick and Skyler, you guys ended up joining later on. How did you hear about the show and what were your first impressions of it?

Nick: I met Clay and St. James and a bunch of other people through open mics around the city. Two Young Hustle members were moving and leaving the show so I took one of their spots.

Skyler: I won a producer spot through the radio. No, I mean we were just friends and it was the next natural step.  

After being a collective for some time now, what’s the dynamic of the group?

That is an interesting question. That’s something we haven’t even figured out ourselves. We are a very collective group and people like our individual comedy for different reasons but we think Clay is the mind behind it. St. James is the pretty face, and Nick and Skyler are our slaves. Just kidding, as far as equal goes, we are all equal.

Skyler: St. James and Clay have been doing the show longest so it’s obviously theirs and they have the most vision of what the show is going to be. Nick and I care about the show itself, but it’s not our baby. We are more of the stepdads and we are trying to be good but sometimes the show still calls us “Brian.”

We are also all just really good friends so this is a 25, 25, 25, 25 thing and we don’t really argue outside of everyday….only an insecure group would have to yell we are all equals. There is always a natural push and pull but we are equal in the sense that we are all ourselves. We don’t say this is a team so leave your attitude at the door, hell no bring your attitude along. It is the perfect chemistry between all of us.

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Last year you guys were able to establish your home at the infamous Laugh Factory. Was making it to the Laugh Factory your end goal?

When you do something great like this, there is no end all be all. Our goal was to put on a great show for friends and family and to get better as comics. There is truth to when our show grows, we grow and when we grow, our show grows. We kept doing better and realized from a business perspective that our white crowd at an alcohol-free Puerto Rican restaurant wasn’t going to be our best crowd. We moved to a place in Roscoe Village for a little bit and then River View and then we sold out a show at a pop up in downtown. From there we came here [The Laugh Factory] to pitch our show. The cool thing was that when we came to the Laugh Factory’s door they already knew who we were and had heard of our show. You work hard and doors open by themselves. The Laugh Factory is the best comedy club in Chicago, so yeah, we belong here, but even without The Laugh Factory, Young Hustle would still be putting on shows and we would still be Young Hustle. Being and performing here is a blessing and we love it here. The Laugh Factory is the perfect place for us and where we really started our run.

How do you guys prepare for your show? Is it a team effort or do you rehearse independently and just come together on the night of the show?

We are all responsible for the show. First off, we all work on our own sets independently. We are all responsible for promoting the show together, to our own separate friends, and our social media. We see each other here and there but since we are all busy working on our own material it is hard to come together. Clay doesn’t do open mic; he’s moved on to doing stand up on the brown and red line. But that is honestly what Young Hustle is all about. We are out here doing things people wouldn’t normally do.

Comedy of Chicago said, “The Young Hustle Show is a stand-up comedy show that has a mix of the hottest comedians from Chicago”, How does that make you guys feel?

It makes us feel amazing. Our goal is to be the best comedy show and comedians in Chicago. The only way to be the best is for us to book the best comics. We don’t just book Chicago comics, we also book New York and LA comedians. We want the funniest comics we can find up on stage with us.

What’re your guys’ thoughts on the Chicago comedy scene right now?

It reminds us of high school. It is the best way to describe it. It is bullshit, but there are people who succeed because they understand if you work hard you can get to the top. But there are also the people, where if you fuck up the right way you can still make it around. It is what it is, I am sure there are football players that hate the NFL. You think it is one thing, but once you get into the scene you realize all the other things it is. It is collateral damage that when you follow your dreams it is not going to be an easy way up. Chicago is a great place to get better because it matters, but to some level, it also really doesn’t. It matters in that we are in it and making friendships and everyone is coming to Chicago for comedy a lot of times, but it is also a great place to fail because stakes are low in that you can suck here and learn to put on a show and make mistakes, but you still get better and better. You attract the type of person you are so if you are going to work hard on comedy, be creative, and be nice, you end up getting those people around you. The comedy community can have downfalls because of its people, because they are human, but those are asses you stay away from. Overall, we really appreciate the Chicago comedy scene. 85% of it.

Where is the craziest place you’ve ever done stand up?

St. James: A hip-hop show in a drug house, they were selling crack outside.

Nick: It was a fundraiser for a web series called Right Swipe and it was a body positivity show. After someone did a rap ballad about eating pussy, I had to follow that and let’s just say it was a weird place to talk about being a man-child.

Skyler: At a different Puerto Rican restaurant from the one where this show started, the owner made room for a dance during the comedy show. Then at one point people at the bar got into a fight so the owner just turned on the lights halfway through the show and kicked us out.

Clay: People weren’t laughing at jokes I was doing on the L, and for some reason, this one guy on the train hated my guts. He was across the train and just yelled, “get a fucking job, you hippie.” So I told him to shut up because I’m working on my craft and he just kept going. So I yelled back and I kind of feel bad about it, but not really…  He didn’t like the response I gave so he chased me off the train at the Fullerton stop and I hid for ten minutes and got back on the train and kept performing.

What is the most memorable response you’ve ever gotten to your stand-up routine?

Clay: I was bombing on the train for 15 minutes and feeling bad about myself so I got on another train. A lady on that train said, “Hey you do comedy, right? I saw you at The Laugh Factory, I think you’re gonna be something.” Or the other day a guy gave me his lucky two dollar bill and said he thought I was going to be something one day too.

St. James: First time doing comedy outside of high school, I snuck into a bar and was way too high. I’m kind of bombing until my final joke which is about me turning 18. The joke does really well but then I get off stage and the host comes over and goes, “Cool, here are some things you do when you turn 18: get your driver’s license, have sex, go vote. Things you don’t do is sneak into a bar and tell everyone you are 18.”

Skyler: Worst reaction I’ve ever gotten is I was doing a joke about who can say the N word and a drunk white guy says it when it is dead silent in the middle of the joke. All the laughs disappeared, and I have never seen a room go from 100 to 0 so fast.

Nick: The best is when I went up and did jokes about looking really young, and they were clearly jokes, but a woman approached me after the show and told me that I could look older if I dressed better. It was the best because it made me laugh harder than I have ever laughed before.

One thing the fans love about your shows are the special guests that join your show. Who is your dream guest to have?

Skyler: Jesus, but comedian wise Dave Chappelle

James: Kanye, Michael Che, and Katt Williams

Clay: Chris Rock, Chappelle, and  Adele Givens

Nick: Donald Glover when he was still doing comedy

Do you have a future goal for the Young Hustle Show now or are just riding the wave at the Laugh Factory?

We want it to be a Chicago staple. Chris Paul the basketball player said, “Confidence comes from practice,” and we work and practice harder than anyone. We see all the people that have come through the show and are a part of it now being successful in comedy and it would be cool if 10, 15, 20 years from now we all come back together and do the show again at the Chicago Theatre or something like that. The Young Hustle Show is always going to be a thing and we are never going to stop performing together or being friends. The show will be as good as we are and we are always going to be good. It is just like having a cool bar, you get a good run and you become the hottest bar. We want to be the talk of the town and we don’t believe in limits. If we could do this show on a space station we would. This shit is fluid. The Young Hustle is wherever we are. The Young Hustle is an idea that we embody.


Written by: Colleen Kennedy

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