And the playground is where he spent most of his days. In fact, Reggie attended the same middle school as Will Smith, but has not met him—yet.  “Conquest is my mom’s last name, and I use it on stage. I started doing stand-up in 2010 in Philadelphia at the legendary Laff House. I didn’t have much life skills, just being funny, a class clown. It was just like 'Oh, this is what I can do' because I’m not into school at all."

Rappers, you gotta live a certain lifestyle to be a rapper. I was always just silly. I hung out with my friends that rapped but there was certain stuff you had to do. Had to be outside all day, be on corners, gotta probably eventually get into drugs and that just wasn’t [me]. I knew being a rapper wasn’t the way to go. Comedy you can be honest. Rappers you can’t really talk about how mediocre your sex is. You can talk about that in comedy.

I worked at an elementary school in South West Philly for like a year. I was the only male in the lunchroom and the kids started calling me “Lunch Lady Boy.” When the school year was over I started doing comedy. I would get off work and have food that the students didn’t eat and hand it to my boys that was on the block. It was summer time and I just said I can’t keep doing this. I was living at my dad’s house at the time, and he was on my back about being a lunch lady. It was bad so I quit.

It was a ’98 Ford Explorer. I sold it and only got $900 for it. It definitely helped. I had that and another $300 for my first month’s rent. To this day I’ve never signed a lease in New York. I got a job working at a school and that’s how I pay my rent. After the lunch room I still had to work a job, so I did stand-up at night and worked a job during the day. My last job was at the Boys and Girls Club in New York. Kids are just so funny to me and they keep you up on stuff. I always worked with kids until I could live off of comedy.

I’m from Philly but I’ve been living in New York for the last eight years. I do a joke about my dad being a cop. In that New York comedy scene I got to see Roy and we just built a relationship. He just texted me one day and asked me when am I available to shoot something. At first, I just responded “Who dis?” And he responded “It’s a n*gga trying to get you some work.” I thought I messed it up but he put me in [his show]. I think I had one line so maybe technically that is my first role. I gotta give it to Roy. Roy Woods, Jr. is a good dude.

I’m still surprised I got on Insecure. I got into this festival Called JFL, Just For Laughs, it’s a big festival they do every year in Montreal. Then I got an agent and went to L.A. for a sh*t load of meetings. My new agent at the time sent me on this audition, and I remember I was the first one to go in. There was like six other fat dudes in the room and we all kinda looked alike. I just signed my name and went in. What made it easy is I went in and it was a room full of people, like eight people.  So, I said I just gotta be silly. And I [got] it like that.

I was super nervous. They would give me lines and then as I went on I got to ad-lib stuff and have more fun. Issa was so cool and she helped me a lot. When I got there we had to go straight to rehearsal, I’m walking behind Issa and I remember being so nervous and we weren’t even naked yet. Issa’s been here, she knows what she’s doing and I’m just following her and we’re rehearsing. She gets on the bed and I’m just standing there like, this is nuts.

Once they drop the robe you can’t prep for it. I didn’t do push-ups or anything. I had so much time to work on my body and work out, or try…I didn’t do ANYTHING. I was in my trailer just texting my friends back home and I’m like y’all are no help. You woulda thought I’dda went on a diet or something but I’m eating all the craft services stuff. It was bad.

While we were doing it, I was sweating a lot. I’m like legit sweating in the scene, so I ask the director [Kevin Bray] if I can wipe it off and he says no, keep it. And I’m like alright. After one cut Issa asked me “Is this your first role?” And I was like Yeah. And she said “Wow, you’re really going for it.” I was working, so when they say “Action,” in my mind we doing it right now.

Calvin is a break from Lawrence and the other guys. One time I saw The Shade Room post the characters Issa’s been with on the show as "Snack, Lunch and Dinner." If they’re the snack, lunch and dinner, Calvin is the cheat meal.

If you know it’s going down and there is already something going on between you and the person, yeah you bring that stuff. I don’t smoke weed or drink Hennessy in real life but I’ll bring a bottle of something. That’s normal behavior.

The craziest thing that’s happened to me at the airport? Nothing too crazy. But every time I see someone with their bare feet it just grosses me out. I kind of want to yell at those people. It’s usually white people. When I see someone going through TSA bare foot I wanna yell “You didn’t know you were coming here? Put some socks on!” They should have somebody set up on the side, “Wear your socks!”

I hope this puts on for a lot of full-size n*ggas. And I’ve never been a take your shirt off fat dude either. I’m in the pool with a swim shirt. This is exposing a lot for me, so I’m definitely nervous. You got the Rick Ross’s out there with their shirt off, but I’ve never been that dude. So, this is huge for me to have my shirt off on a show. It gives me some confidence. 

Follow Reggie Conquest on Instagram at @ReggConquest