On success, self-doubt, and learning how to be funny

So we’re roommates, and you set up the wifi network, and the password that you chose is cooldude5. Is that how you would describe yourself?

Yeah. No. I don’t know. When I first got a bank account, when I was 18, they asked me what my password would be, and I said, “cooldude.” And then it’s gone up—cooldude1, cooldude2… it’s gone up since then to five. It used to be that cooldude5 was my password for everything. And then, I used to say that on stage, because I had nothing to hide, and say, “My password to everything is cooldude5.” And then Mitra [Jouhari] made me change my passwords for everything.

But, I don’t think I would describe myself as “cool dude five.” There was a time period where I just would say “cool dude” a lot. And, I would say I wanted to start a production company called CDNG, which was Cool Dude Nose Grab. But nope, I don’t think I would describe myself as a cool dude. I’d say I’d describe myself as the opposite, which is more of an anxiety-ridden-tired dude.

Well, let’s say you’re at a party and a stranger asks, “What do you do?” What do you say?

It depends where I am. If I’m in LA at a party where I know people there, I might say, “I’m a comedian.” But, if I’m in Alabama, I say, “I don’t know, I’m just trying to figure it out. Chasing the dream.” Like, “Oh, what are you doing out in LA?” I go, “Oh, I don’t know. Showbiz, I guess. Trying to.” Because if I’d say comedian, a lot of the times, that person that I’m talking to—it evokes something in them, and they become their real bad self. It’s a really good gauge. If you tell somebody that you’re a comedian and they say, “Do something funny.” Or they say, “You don’t seem funny.” Or they say, “Tell me a joke.” Then often that person is bad and has done some bad things in their life.

So I try not to tell people I’m a comedian unless it seems like they probably know other comedians, or they’re just cool. Because I’m not like a conversationally funny guy either.

How did you end up a standup comedian?

Trying to be an actor… Then I was doing improv at the Upright Citizen’s Brigade, and I was having a really hard time making friends there. So, I started hosting my own show with my friends that weren’t comedians, but we just had been making videos together, little weird short films and stuff. And I was trying to get people from my UCB class or people who I had seen at UCB to come do my show with sketches and improv, but none of them would leave the UCB because the UCB is a really good venue and this one is sketchy, not as consistent. So, I asked stand up comedians. And then I would host the show. And then, because I was having stand up comedians on the show and they saw me hosting the show, they would just invite me to go do their shows.

And then I became like, “Oh, well, I’m not really a standup, so I should do open mics all the time.” I just was really bad at it initially, but I wanted to figure out how to be good at stand up. So, I became fully obsessed with it, and it became my whole life. And in those six months of me trying to figure out how to get a single laugh on stage, I was like, “I’m not very good at this, but I’m addicted to it, so maybe it’s something that I should be doing.” That’s kind of the weird backwards way of doing it.

Photo by Kailee McGee

What are you working on right now?

Working on a stand up comedy special that will include all of the jokes and comedy music that I’ve been making since I started doing comedy.

Where are you at in that process?

I’m just finishing it up, I hope. We’re almost done with the edit, and I think it’ll come out on a secret network in February or sometime early next year. But hopefully people like it, because it’s hard to edit your face sweating on stage.

How is everyday Whit different from the Whit who shows up on stage?

I think before I did stand up, I was a much more annoying person because I was so desperate for validation, and I still am. Everyday Whit… the thing about me as a comedian that is different from other comedians who I really like is—they are just funny. Whereas, I have to be tap dancing on the stage in order to figure out how to be funny. So everyday Whit is probably not as funny as onstage Whit, and more alienated than anything. I’d say, I don’t know. I feel like you would know better than I would.

Before we met, I saw you perform. You were onstage, kicking your legs and screaming wa-a-a-h! and all this stuff. Then I met you and we became friends, and I feel like you are totally different. You’re a very mellow, warm, tender, and nice person. And, pretty quiet, sometimes.

I’d say I’m pretty quiet. I’d say the takeaway is that people always say I’m pretty quiet. And, yeah, maybe sometimes a little bit guarded. But then on stage, I’m so not mysterious or private at all, so that’s how I’m different. I just don’t know how to be very funny in the daily world. I have to be the center of attention in order to be funny, and it’s bad. In school and stuff I wasn’t funny really. So maybe that’s the main difference… The funny level is different. And, the loud level is for sure different.

Do you ever have moments of self doubt? When does it happen and how do you work through it?

Yes, all the time. It’s an everyday thing, and I don’t think I work through it. I wonder if there is a way to ever be satisfied. I don’t really think there is. I think no matter what, if you’ve chosen to do something in the world of showbiz, it means that you need something—you need a bounce back from the universe that you’ve never really gotten. And because of that, you’re always going to be down on yourself. Hopefully, you’ll end up making things that connect with people for that reason. But in the meantime, I think that I’ll always feel like what I’m doing is cheesy or lame or naval-gazey or too silly or too stupid. There’s never going to be a time when I feel confident about a decision that I’ve made. I’ve just decided I’m going to be embarrassed of what I do, and I’m always going to feel like I don’t deserve the opportunity. Because yeah, I don’t ever feel like, “Now is my time. Here I am, finally!” I always feel like, “What the hell?”

I think that you just have to figure out how to do other things that you don’t doubt. For me it’s skateboarding, and it used to be music, but now I do that in my comedy. If I didn’t go skate and stuff, I think I would fully be crazy and nuts. The other thing that makes me stop doubting myself is to watch things and listen to things that make me feel inspired.

And what’s so sad is I doubt myself literally until the moment someone tells me, “I think it was good.” And then I go, “Okay!” And all the doubt is gone for a day. And then I go to sleep and I wake up doubting myself again. It’s the first thing I think about every morning no matter what. The first thing I think about is that I’ve made a mistake. And then hopefully, throughout the day, people are nice to me and then the doubt goes away to where I can fall asleep, and then I wake up again and start all over.

What does success mean to you?

I will feel successful if I can pay my bills without having to worry, and I can just not feel like I’m having to make something all the time. I think I’ll feel successful when I feel creatively fulfilled or on the right track. If I had a career where I didn’t have to worry about money, and I made a short film every year that I could post to Vimeo or whatever that people really liked and that I really poured my heart and soul into, I think I would feel successful. And if I didn’t have to worry about money, and I had friends who made me feel good who I liked hanging out with.

And then the other version of success for me is this pathetic dream of being some type of successful comedian person and telling people, “Oh, you can see me tonight on whatever it is… on Showtime… or something. Or, you can go see my movie.” But really, it’s just making things that I’m really excited to be a part of. And also having some type of money, some financial security. And then hopefully one day a family or something like that, I think. I don’t know anybody who is mega famous. I don’t have any close friends who are mega famous. I doubt that they think of themselves as being… well, they probably do think of themselves as being successful but not satisfied.

Photo by Kailee McGee

You do stand up, you make music, you write and direct movies, and you skateboard. Is there a through line across your mediums?

I guess it would probably be that if you were to turn off the sound you might think that it was cool. Or, with my music, if you were to not really pay attention to what I was singing, maybe you would think it was a real song. And with skating, it’s like, if you didn’t pay attention to how my face in the skate video that I made is me with the baby filter on it, you might think that I’m just a guy who does cool skate tricks. That’s kind of the through line, like, I love these things that are considered cool, like skating or goth music, but I can’t remove the silliness out of it.

So, yeah, I desperately want people to think I’m freaking cool, and also hopefully think that I’m a dumb ass and silly and funny, too. Desperation is the through line, probably.

What is your relationship to your devices?

When I’m happy, I don’t look at my phone and stuff very much. When I’m unhappy, I’m obsessed with it; I’m always looking at it.

Sometimes, I’m unhappy and then I make something—same thing, desperate for validation. I make a video, and I post it onto Instagram or something, and then I’m obsessed with seeing how people react to it. I look at that way too much. I’m at a point where it’s the first thing I look at in the morning. I’d say my relationship with my phone is overall not good, at least with social media. But with apps and stuff, I love that. Taking people’s faces and turning them into The Joker and stuff. That’s probably healthy, right? Because that’s creative.

What advice would you give your 16-year-old self?

Loosen up, talk to people more, party. If a girl likes you, don’t be weird and vice versa. Because I was so punk, and I wanted so desperately to be different than everyone, I wouldn’t drink or anything. And it made me… I think I really alienated a lot of people because I made them feel uncomfortable with how I was. Maybe they thought I was judging them, and the truth is that I probably was. I had some chip on my shoulder.

If I talked to my 16-year-old self, I would tell him, “Don’t be so obsessed with running away and moving away. And, don’t be so critical of other people.” I was just a textbook punk kid who liked punk stuff and hated anything that was popular. Looking back, I probably was kind of a jerk. Senior year of high school, I loosened up a lot. But, when I was 16, I didn’t. I lived in this fantasy world where I was the one punk in Alabama, which wasn’t true. But yeah, I think I would tell myself to loosen up for sure. Don’t be so serious and have fun.

Photo by Kailee McGee