A Conversation With Wyatt Cenac On Funny Rappers & Questlove Making Him Join Twitter

(AllHipHop Features) In the final part of my conversation with comedian Wyatt Cenac, the host of the Night Train web-series divulges which emcees keep him laughing on a regular basis.

The connection between Hip Hop and comedy led me to also ask Wyatt why his official Twitter account only follows The Roots drummer Ahmir “Questlove” Thompson. Cenac’s story involves him explaining how Questlove potentially cost him $1 million.

With Night Train now available for streaming on Seeso and People Of Earth set to premiere on TBS, Cenac keeps his plate full. Discover some of the comedic projects the New York resident is sharing with the world in the third installment of our interview.

[ALSO READ: A Conversation With Wyatt Cenac On ‘Night Train’ Series, Media Conglomerates & Women Having Babies By Aliens]

You’ve worked with Questlove, Jay Z, Slim Thug, and others. From your experience, who is the most naturally funny rap star that you’ve met?

The person I talk to the most that makes me laugh is Jean Grae. I think she’s somebody that I’ll have come do my show sometime. Because just talking to her, she just naturally has funny thoughts and opinions on things. She’s somebody that often makes me laugh a lot.

Tariq [Black Thought] from The Roots is funny because you don’t expect it coming from him. He’s just got such a gruff voice and then he’ll do or say something silly that just goes counter from what I’ve heard come out as his voice on song after song.

Speaking of The Roots, why is Questlove the only person you follow on Twitter?

He’s the person who set up my Twitter account. I didn’t actually want a Twitter account. One day, I was with the comedian John Hodgman, and he was with one of the founders of Twitter.

Me and my friend Chris were going to see a midnight screening of the Thor movie. So we met with John and the Twitter guy. They weren’t going to the movie, so as Chris and I were leaving, the guy from Twitter was like, “Live tweet the movie.” Neither Chris or I had Twitter. I remember thinking, “No, pay me. You want me to promote your thing for free? At least pay for my movie?”

I thought about doing this thing where I would try to shoot a couple of videos as an online campaign for what my tweets would have actually been if I had Twitter. Basically, do that as an attempt to get that dude to give me a million dollars.

He wasn’t going to do it. But I’d do a bit where I was going to say, “This dude from Twitter asked me to join Twitter. Here’s an example of some of the things I would tweet if I had Twitter. But because he asked me, and I know Twitter makes millions of dollars, I’ll join Twitter for $1 million.”

Obviously, he wouldn’t give me money. It was just a stupid bit. As I was planning to do that, Amir [Questlove] signed me up for Twitter independently behind my back. He was like, “Here you have this thing now.” I was like, “No! You gave me a Twitter account, and I lost out on a million dollars!”

How often do everyday situations like that spark these million dollar ideas in your head?

[laughs] It was a million dollars in my head. I don’t know how much it was worth in street value. The interesting thing about working in TV, film, and also this digital space is the landscape is so vast now. So I think I go through the world a lot of times looking around thinking about things as far as… “Oh yeah, that might be an interesting thing if I was writing a script.”

This little interaction might be something that sparks an idea, “Okay, maybe I’ll hold onto that if I ever write a movie script about this or that” or “that would be an interesting thing to do as a little web video.”

Some of those ideas I get to flesh out and make. Some sit as ideas that never get to see the light of day. I probably have a drawer full of ideas that could have been. That drawer is probably more full than the ideas that actually have been made.

So you have Night Train [out now] and People Of Earth coming later this year. What else can we expect from Wyatt Cenac in the coming months?

That’s a very good question. I think I probably need to figure that out myself. We’re going to start filming People Of Earth, so at least for the next three months, I’ll be in Canada shooting that show.

For three months, I won’t be able to get on stage as much as I have been. Hopefully, I’ll come back hungry to get back on stage. Maybe even with some new ideas I can talk about. Furry Dumb Fighter is coming out on vinyl at the end of the summer. For people who love a dead medium, there’s a vinyl record coming out.

[ALSO READ: A Conversation With Wyatt Cenac On Smoking Weed, Being Awed By Kevin Hart & The Success Of ‘Daily Show’ Alumni]

Night Train with Wyatt Cenac is available for streaming on Seeso.

Follow Night Train on Twitter @NightTrainShow and Instagram @nighttrainshow.

Follow Wyatt Cenac on Twitter @wyattcenac and Instagram @wyattcenac.

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