Talking with Brendan Gay, something sprang to mind. It was a conviction I have, but don’t often say – that comedians are the high priests of our culture. They articulate issues that we don’t know how to express. They reveal perspectives we hadn’t considered. They’re unflinchingly honest. Whatever insight they bring, they lift us up and connect us. Share a laugh and nobody’s a stranger. I thought about all this because everything Brendan was telling me exemplifies this theory.

When Brendan was just one year and three months into his stand-up career in Chicago, he made a bold move. He decided to get in his car and do a “52×52” tour. That’s fifty-two cities in fifty-two weeks. Over the course of the year, he said, “there were endless things to learn.”  Brendan grew up in Minnesota, one of the only biracial kids in his town. The experience ingrained a profound sense of what it’s like to be different, feel different and to be looked at differently. But as he traveled across the country, this truth began to co-exist with an additional truth – that we all have way more in common than we realize  – and that the pain of feeling different can make for great comedy.

He is also resilient. When I asked what his favorite story was from the road, he told me “a struggle story” that was “the worst day of my life.” As bad as that day was, he turned around his fortunes the very next day.

Shortly after returning to Chicago, he decided to move to New York to take his career to the next level. He now produces stand-up showcases at The Bowery Electric and at The Stand Comedy Club. He hosts a podcast with plans to launch another. He was a finalist on TruTV’s Comedy Breakout Initiative at The New York Television Festival, a Finalist in the Make Me Laugh USA Competition, and Semi-Finalist in NBC’s Stand-Up Diversity Showcase.

On March 20, he returns to Chicago and becomes the first comedian to record an album at the Lincoln Lodge’s new theater. Brendan kindly spoke with me by phone about his powerful perspective, the key to building a comedy career (it has to do with who you trust), and why, despite his success, he is still “a comedian who smiles confidently when he’s nervous.”

STARTING OUT ON THE PLAINS

Teme: What did you do before comedy?

Brendan: My first career was medical device sales. My territory was Montana and Wyoming which was beautiful, but it was only fun for two weeks. I was 21 and I was so bored. I drove three hours a day, so I listened to podcasts like Mark Maron, Joe Rogan and Bill Burr. I started to think, “What do I actually want to do?” I went to an open mic in Montana just once to check it out and I loved it. So I quit my job and two weeks later I was in Chicago where I started comedy.

WHY COMEDY?

Teme: What about comedy inspired you?

Brendan: You can really express yourself. I love writing jokes. There is no better feeling than being on stage and actually creating something that people enjoy. Which, now that I’m saying that, I realize, “Oh, I love attention!” As soon as I did it, there was no turning back.

STARTING OUT AND BOUNCING BACK

Teme: What was the first open mic that you did in Chicago?

Brendan: The first mic I ever did in Chicago was four years and two months ago. It was December 8th, 2015 at Durkin’s Bar. No one laughed except at one joke and that’s all it took for me to like it.

After I was in Chicago for a year and three months, I decided to tour the country for a year. I went to fifty-two cities in fifty-two weeks starting January 1, all the way to January 1 a year later. I was back in Chicago for a year. Then I moved to New York. Do you do stand-up?

Teme: I did a little bit a long time ago. I’m not an on-stage person. But I think doing stand-up is the greatest feeling in the world. It gives you so much energy whether you’re on stage or in the audience.

Brendan: When you do well it’s the best. Oh my god, when I do bad it’s the worst. The worst feeling in the world.

Teme: What do you do to bounce back if that happens?

Brendan: Oh man, you just get on stage the next day. It’s a classic quote, “You get knocked down seven times, you get up eight.” Let’s say one night I have a really bad night. What I like to do is get back on stage immediately. Go to another open mic, get on another show.

A STORY OF CHANCE

Teme: Do you have a favorite story from your time in Chicago?

Brendan: Does it have to be comedy related?

Teme: No, not at all!

Brendan: One time, I was walking a dog and I was listening to Chance the Rapper, to one of his new songs. Then this guy comes up to me and starts petting the dog. Then he looks up and he says, “You have such a good dog.” And that person petting the dog was Chance the Rapper! I was like, “Whoa!” So now I’m a fan for life.

52×52

Teme: Of course, I want to ask you about the “52 Cities in 52 Weeks” tour! How did you decide to do it?

Brendan: I saw great comedians like Dave Chappelle, Hannibal Buress and Sarah Silverman. They went on the road. So I was like, “Oh, in order for me to be the best, I need to go on the road.” When you go on the road you see what’s actually funny, you can test a lot more jokes, and see different types of audiences. So I took three to four months and mapped out my schedule. I asked at work if I could work remote. I was a year and a month in [to my comedy career] and I just decided to do it.

Teme: Did you find that people laugh at different things in different places?

Brendan: Oh, yeah. One hundred percent. Chicago is very midwestern. People are more polite and conservative. More moralistic. You go to California or to New York, they’re way more liberal. You’re able to swear more. You’re able to say more radical things. I’m not saying that’s better comedy. I love the Midwest. I performed in the Midwest mostly and I prefer it. But definitely people laugh at different stuff. You go down south, the jokes are going to be completely different than in Portland, Maine.

You can be yourself, but you’ve got to have awareness of the room. You’ve got to sit in the culture. It’s like if you were the only minority in the room. People just look at you different. You’ve got to change jokes to make them work and make people laugh.

Teme: How did you prepare?

Brendan: You really don’t. You’ve got to throw yourself in the water. I’ve been on stage thousands of times, so I guess how I prepare for it is just all the experience that I’ve had on stage.

Teme: Where did you start the tour?

Brendan: I started in Miami because it was January 1. I needed to start somewhere warm. So I stayed down south and I kept going west. I went to Atlanta. Then I went to Louisiana and Alabama. Then eventually, I went to Mexico and up through California. I went to the Pacific Northwest and then the Midwest. My last city was in North Carolina. When I was done, I drove back to Chicago.

Once I was done I was kind of sad. I mean, don’t get me wrong, it was draining, but there were memorable moments in each city. I’m really glad that I got to do it.

Teme: Wow, what an adventure. There’s a great book in that.

Brendan: Oh my god. I tried to write it. I have all my journals. I just moved to New York instead. I didn’t have time. I’ll get there eventually.

Teme: I’ll pre-order it right now!

THAT TERRIBLE NIGHT

Teme: Do you have a favorite story from the road?

Brendan: My favorite story was a struggle story. It was in Hoover, Alabama at the StarDome Comedy Club. It’s a theater with 600 seats. And I’m on my way there. I’m already late and my car breaks down in the middle of the highway and I had to call Geico or something, and they had to pick it up. I had to pay money and I didn’t have the money. I got to the comedy club and I’m late. I’m going on stage in two minutes after my car just got towed and I don’t even know what’s wrong with it.

So I go on stage and I bombed. I do so bad. Like crickets in the audience. Then the next guy who gets on stage does so well. Just murders. And I’m sitting in the green room so sad. And then the headliner comes up on stage and for the first three minutes of his set he is just making fun of how bad I did on stage. And the crowd is loving it. It’s going so great. And I was like, “Oh, my god. This is the worst day of my life.”

I had to pay a thousand dollars to get my car fixed and that’s money I didn’t have. I didn’t know where I was going to stay.

But the great thing is, I had a show the next day. And I did so well. I was like, “Oh, this is what comedy really is, it’s just a roller coaster.” There’s ups, there’s downs. You never know, but you just got to keep going and get better. It was only week five or six [into the tour]. So I was like, “Okay, if I can make it through this, I can make it through all fifty-two weeks.” So yeah, that’s the story that I’ll never forget. Hoover, Alabama.

52×52: PERSONAL AND PROFESSIONAL

Teme: How did the tour change your life personally and comedy-wise?

Brendan: Oh man, let’s start with personally. There’s an endless amount of things to learn. I got to meet so many different people. I got to learn that everyone is the same. Everyone has their problems. Everyone has their life experiences whether you’re in Iowa or Florida. There are different cultures. People may eat different food. They may have a different language or communicate differently. You have your nuances within politics. But everyone is still the same everywhere. Doesn’t matter what color or race you are.

But oh my god, comedy? I got so much time [on stage]. I got to see what was actually funny. I got to be in front of real audiences across the country. It makes you so much better as a comedian to get that exposure and experience, to struggle somewhere else and to do well somewhere else. I got to do theaters in front of thousands of people. Other nights, I got to do The Comedy Store in front of three people.

It made my material sharp. It made me work on long form sets doing thirty minutes, doing an hour. It made me connect with other people across the country, so now I get more work. It boosted my career significantly.

NEW YORK

Teme: How did you decide to move from Chicago to New York?

Brendan: I wanted to go to the next level. I wanted to be doing it with the best of the best. New York City has the best comedians, not in the country, but in the world. When you see Dave Chappelle, Jim Gaffigan, Mark Normand, Jerry Seinfeld … if you see people go up like Chris Rock and Michael Che in a single night, that’s a college education.

Teme: It’s got to be incredible seeing people like that all the time.

Brendan: I run a stand-up at the Bowery Electric. We have Todd Barry come in, Sarah Silverman. Roy Wood Jr. is going to be on the show. I saw Bill Burr perform five times. That’s something you don’t get to see when you’re in Chicago.

HOW TO BEGIN AGAIN

Teme: When you moved to New York, you had momentum from your tour. How do you keep that momentum going in such a big scene?

Brendan: It was really hard. I had to start over. I’d been in New York when I was on the road. I had some connections, but you got to go back to square one. You got to start hitting the open mic scene a lot. You’ve got to meet all these people, go to the shows and introduce yourself. You got to prove yourself in the biggest city in the world. You got to build your own momentum again. So that’s why I produce the show. That why I’m producing another podcast.

The great thing is, you can get exposure here. I did a show at a comedy club and Jimmy Fallon’s booker was there and we exchanged contacts. It doesn’t mean I’m going to be on The Tonight Show, but industry is in the seats at these comedy clubs. So make yourself get out there. That’s a good way to build momentum.

INNOVATION IN ICELAND

Teme: Overall in your life or career, what is the best thing that has happened so far?

Brendan: The fifty-two cities in fifty-two weeks was insane. This album’s going to be insane, but it hasn’t happened yet. I was part of a team of comedians that shot a pilot in Iceland called Funny Planet.  The show is us finding out what’s funny around the world. It’s like Anthony Bourdain but with comedy.

We got to interview the former mayor of Reykjavik who was a comedian. We also got to perform there. We submitted the pilot to the New York Television Festival and we became finalists to have it produced by truTV. I’m just a comedian. I just want to tell jokes, and now it’s like we’re these serious people who might have a TV show. That was pretty insane. We got to shoot a pilot. We actually did it.

A MAJOR SECRET TO LIFE: TRUST YOURSELF

Teme: You’ve said that something that helps you move forward is trusting yourself. How do you build that trust and what does your inner dialogue sound like when you trust yourself?

Brendan: That’s a really good question. If you don’t trust yourself, who else can you trust? You are all that you have. You got friends and you got family. You’ve got co-workers. But at the end of the day, it’s just you. So if I don’t trust me, my whole life is shambles.

I think the strongest people are the ones who trust themselves and excel because they’re accountable for themselves. They have no one else to rely on. They’re not entitled. They got to trust themselves to do something. If you really trust yourself and believe in yourself, you’re able to do so many things and push yourself further. How? I look back on the stuff that I’ve done. I try new stuff. And I haven’t died yet.

Teme: That’s such a great answer. I have trouble trusting myself because I’m afraid I’m going to fail. But it sounds like you can trust yourself and still be open to any outcome.

Brendan: Yeah, you’re right. Of course I’m going to fail. I’m going to feel sad. I’m going to feel scared. I’m going to be hesitant. I’m going to be lazy sometimes. But keep going and trust yourself. You’re going to be fine. If you really do trust yourself, you’re going to have less anxiety and less worry. So it’s going to push you further. You’ve got nothing to worry about. You have yourself. You know yourself.

Teme: That’s so brilliant. And if things ever go wrong because that’s life and it’s inevitable, you just trust yourself, “I’ve done this before. I can deal with this.” And get through.

Brendan: Right? That’s a really good point. Yeah, you’ve done this before. Teme, you survived. Whatever’s bad that’s happened to you before, you’re still standing, you’re still moving. You’re still doing interviews. You’re still writing. You’re still going. So, it’s like, “I trust myself. I’ll be fine.”

Teme: I can’t wait for your book.

Brendan: I’m still learning. I have so much to learn. And so much to get better at.

NERVES …

Teme: You’ve said that when you’re nervous you smile confidently. How did you learn to handle nerves with a confident smile?

Brendan: Stand-up comedy is where I learned to smile confidently when I’m nervous. When I started and I wasn’t funny and a joke didn’t go well, I learned you just smile and move on. The emotions are going to come, but just smile and keep going. It’s going to make things a lot easier.

FAVORITE TOPICS

Teme: What are you favorite topics to talk about in stand-up and what does your comedy say about you?

Brendan: I love talking about my friends, and experiences that I’ve had that trigger emotions; that have been scary. Or things that have been the most fun times in my life. My childhood. Anything that was very impactful. I’m very observational. I do some race stuff, too. I talk about family stuff. Anything is funny. A lot of my comedy is me trying to figure out who I am as a person. I’ll even say that on stage, “I don’t know who I am yet. I’m a 27 year-old millennial, still trying to figure it out.”

Teme: Your comedy includes observations about minority culture and growing up as a millennial. How do these experiences impact your perspective?

Brendan: A lot. I’ll say that. How deep do you want to go? Being a black person in this all white town, who’s very broke in one of the wealthiest cities in the country … You’re so different from everyone else. Just imagine coming into this world noticing, oh, you are not like everyone else. So you are right away feeling, “Oh my god, everything I do is different. People look at me different just based on the color of my skin.” That dramatically changed my life. I’m going to think differently than everyone else automatically. I’m willing to say things about that in my stand-up that other people aren’t willing to say.

But here’s the thing I was telling you. On the road, I was like, “Oh, I always thought I was so different from everyone.” But going on the road, I was like, “Oh, everyone’s the same.” Everyone feels that they’re out of place. Everyone has different things about them. They have anxiety or feel like they’re an imposter or they feel like they’re not good enough. Everyone has problems. It doesn’t matter how rich you are or what color you are or what your status is. Everyone has it. We all have the same roots.

But it definitely changed me, growing up differently, being broke in a rich town, and being a different color skin in an all white neighborhood. You’re going to think different. Have a different perspective. Because people treat you different.

Teme: Do you think that feeling different is good for comedy? It’s painful to feel different, but it gives you a unique perspective.

Brendan: I think that it is awesome for comedy. When you’re able to laugh about something traumatic and make everyone else laugh, that is an amazing moment. I’ve had people come up to me at my shows and say, “Thank you so much. I feel that way, too,” especially when I talk about race. Dave Chappelle talks about race, racism, and the civil rights movement. That’s serious stuff, but he takes all that trauma and makes it funny. That shows a lot about the person who’s on stage. He’s able to be stronger than the controversy.

YOU’RE INVITED: LIVE ALBUM RECORDING!

Teme: Of course, I want to hear about your album recording! What will your show be like?

Brendan: It’s going to be pretty crazy. I’m going to do forty-five minutes to an hour. I’ve been doing comedy for four years and two and a half months. It’s going to be all the jokes that have hit, that have gone through the road, and about my life. There’s going to be a lot about growing up. It’s going to be an introduction to who I am as a person, where I am right now and everywhere that I grew up, and my perspective on life. So the 27 years that I’ve lived, you’re going to hear about all of those 27 years within an hour. That’s what this album is. It’s an introduction to Brendan Gay. You’re going to know exactly who I am.

Teme: What do you want the audience to take away?

Brendan: I want the audience to laugh and have a good night. To not think about their work, not think about struggles in their life. I want them to know how we can change the world for the better. I know some people rip on that, but the best comedians to me can make something funny out of serious moments.

Teme: Absolutely anything else you would like to add?

Brendan: I’m really looking forward to coming back to Chicago because that’s where my comedy roots are. I’m looking forward to performing in front of the people who made my comedy career. It’s like coming back home after you’ve been away for college. You know that feeling? You come back for Thanksgiving and you see all your friends. They’re like, “Oh my god, you’re so different. You’ve changed.” I want to show Chicago proud.

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Brendan Gay’s album recording is Friday, March 20, 2020 at The Lincoln Lodge, 2040 N. Milwaukee Ave., Chicago. Shows at 8:00 p.m. and 10:00 p.m. Tickets at brownpapertickets.com/event/4484865

More about Brendan here.