Wyatt Cenac On His New Comedy Show ‘Night Train,’ Donald Trump, And What Brooklyn Means To Him

Wyatt Cenac may have achieved national recognition as a correspondent on The Daily Show, but it's Brooklyn, New York, and particularly the borough's intimate comedy venues, where he feels most at home. In 2012, the same year Cenac left The Daily Show under dramatic circumstances, he began hosting Night Train, a weekly Monday night comedy and music showcase at the Littlefield in Brooklyn's Gowanus neighborhood. And while it may be Cenac's fame that draws some audiences, they end up encountering a rotating roster of some of New York's most gifted comedians, from big names like Eugene Mirman to rising stars like Phoebe Robinson. 

Last week, Seeso, a streaming service devoted to comedy, debuted a filmed version of Night Train that will run for six 90-minute episodes. We spoke to Cenac about bringing Night Train to television, the nature of success in show business, and his personal connection to Brooklyn.

What are some of the defining characteristics of Night Train?

We’ve been doing the show for almost four years now, and what stands out for me is the comedians that we are able to get on the show. We’ve created a place that comedians feel comfortable, where they can explore and do things.

Is it stressful creating a show in a landscape where there is already so much content?

Yes and no. I was honestly more excited to actually get to make something. There are plenty of things I tried to make and have not been able to make them, and so to get to make something, I think that was the victory. And to me, the sign of success is that there’s a network that’s interested in letting us make something, and giving us the freedom to make it in the way that we want to make it. Hopefully, it will be successful for them on the other side, but I was more interested in making it than I was thinking about how many people are gonna watch it.  

Do you hope that this show provides a particular snapshot in time for future viewers?

I do. The hope is in five years somebody discovers it and watches it and gets a sense of this particular moment in time, as far as what comedy is like in New York and Brooklyn right now. I know for myself, every now and again on HBO, they’ll show some of the young comedian specials from the ‘80s and early ‘90s, and it’s just fascinating to watch those comedians—some of whom are people that are world famous like Chris Rock or Judd Apatow—to see the jokes that people had, but also the way everything looked. Hopefully, somebody else down the line might look back and find our little show fascinating in a similar way.  

Do you ever watch the comedians on your show and think you might be watching the next great comedy superstar?

I don’t, and that’s not an insult. I don’t have that gauge. I don’t know what people are going to latch onto. There are plenty of people I’ve seen and thought that person is funny, or that person is really talented and they’ve got something, but maybe the buying public doesn’t see the same thing I see, or the stars don’t align in the right way for them. I feel like I’ve seen a lot of talented people, and some have gone on to great things and some have gone on to successful careers and done alright but without great amounts of fame and recognition.

Do you think luck plays a factor in any type of success?

I think hard work is definitely a huge thing, but there is something, if you want to call it luck or whatever—a window of opportunity—that is totally outside of your control, and it’s that thing that will sometimes separate a good career from a great career. I think there are probably hundreds and thousands of stories, not just comedians or entertainers, but people who, if they had shown up to this venue the day before, this person would have seen them, and maybe that would have been their ticket or their big show got canceled because of rain, or whatever those things are. For all the hard work in the world, there’s something to be in the right place at the right time.  

Were there any opportunities in your career that you wish you’d taken?

Not really. They say hindsight is 20/20, but when I look back at stuff, I don’t see it as, "Oh, this is a missed opportunity." When I look back at all of it, it feels like this is the path I had to go on. I got a lesson in that early on—a lesson it took me ten years to learn. When I was 22 or 23, and I was living in Los Angeles and working as a production assistant on The Late Late Show with Craig Kilborn, one day, I got a phone call that Saturday Night Live wanted to fly me out to interview for a writing job. I didn’t get the job and I was really bummed out about it because one of the things I had always wanted to do was Weekend Update. And so for a long time, I was really angry and frustrated with myself, like, "Oh, this is your window and you didn’t say the right thing to get that job." And 10 years later, I wound up getting hired on The Daily Show, and I remember thinking, "It’s funny because I wanted to do Weekend Update, and now I’m kind of getting to do that, but on a show that didn’t exist in that way ten years ago." So if I had gotten that job at 22 or 23, I don’t know if I’d be any better for it. I didn’t want a business card. I wanted the actual experience of a job where I could make topical comedy. I got it, it just took me 10 years longer than I thought.

Speaking of looking back, how do you look back on the period after your appearance on Marc Maron’s podcast, when the internet erupted thanks to some honest comments about your relationship with Jon Stewart during your time on The Daily Show? Do you regret being so open about it?

I was sharing an experience that I had, so I didn’t regret it. As I said on the podcast, everything I had said I had already spoken to Jon about. I was sharing something from a place of, "Oh, this was something that bothered me, but it doesn’t really bother me anymore, and it’s a part of my growth." When I look back at it now, that doesn’t change. To me what changed was how people chose to take that and create whatever narrative they wanted to, whether it was about me or about Jon. And the narrative that they spun had little to do with me or him; it was about validating a narrative that they wanted to spin. I’ve got no real control over that.

Did that experience then make you more wary of sharing certain things in the media?

Not really. There’s an honesty to getting on stage and talking about shit, and that’s a similar honesty that comes out in podcasts or interviews, and I don’t think that experience made me wary of that. It made me more aware that what you choose to say, somebody else can hear it however they want and do whatever they want to do with it. All I can do is be true to myself. I’m always going to make mistakes—that’s inevitable—but at least if you’re owning up to your truth, and you present yourself as an open person, then you can learn from your mistakes.

As someone who’s performed topical comedy on The Daily Show, what is your current platform for addressing the current election and the rise of Donald Trump in particular? 

If I want to talk about stuff, I have Night Train. It’s obviously not the same sort of broad reach as getting on television, but it’s a place where I can get in front of 200 people and talk about whatever I want. On some level, it’s kind of enough for me because with a lot of that stuff, my interest in talking about Trump and Hillary, it’s not that high. Yeah, it’s weird that Donald Trump is seriously being considered as President of this country, but I also feel like my take on it is more a comment about our society than it is about him. And I could dive into that for a while, but on some level, I’ve talked about those things already. I’ve got three albums talking about some of those things, and some of it gets exhausting. And I look at the current landscape of late night shows and the headlines that people write, and I’m very curious about what our perception is as an audience.

After the shooting in Orlando, some website did a roundup of how each of the late night hosts dealt with it. To me, that was a larger comment than any of the late night hosts comments. It felt like grief and compassion, and trying to make sense of all of that, commodified in a way that we are now ranking who has the best take on a tragedy and who has the best take on giving my outrage and my feelings some sort of catharsis that could possibly let me off the hook as a viewer, and that’s where I got worried. It’s nice to have those platforms, but there’s something strange about it, if those platforms become a thing that lets people off the hook, like, "Oh, I felt bad, but then I watched this show and they expressed everything I was feeling and let me get it all out of my system. And because it’s all out of my system, I don’t have to write my congressman and tell them that I want them to do something about gun control. Or I don’t have to do something in my community to affect change."

[Editor's note: NYLON was one of many websites that did a roundup of late night host comments, in conjunction with a news story, a critical analysis, and a list of ways to help.]

Switching topics, what is it about Brooklyn that you feel particularly connected to? 

It feels like home. My grandmother lived here, so Brooklyn reminds me of being with her. On some level, it’s probably the most childish reason to be here, because it’s me trying to hold on to and recapture some bit of my youth that was connected to my grandmother. When I think about New York, I think about it as Brooklyn first. I lived in Manhattan for a year, and it didn’t feel like home to me.

What do you think about today’s Brooklyn compared to the one you grew up in?

It’s different, and that’s okay because it sucks for some people and it’s great for others, but that’s what it’s always been. The Brooklyn I knew as a kid, nothing will top it because that’s the Brooklyn I knew with my grandmother. The moment she left Brooklyn, part of it died for me. So as much as I love it, there’s probably some undercurrent of me walking through a sort of memorial for her that is little reminders that keep me connected to her and to those memories. And I would imagine that there is a kid now, and she or he is having the time of their life in Brooklyn, and their version of Brooklyn is way different than mine. It might be way safer than what mine was, but it’s still magical for them. And in 20 or 30 years, they’ll be an adult and think, "Yeah, it’s not the same, and it’s never going to be the same," but that’s kind of what this thing is built on.