Comedian Kevin Hart on developing stand-up routines while juggling entertainment company, venture capital fund

There have been plenty of successful stand-up comedians, but few who’ve managed to do what Kevin Hart has. In addition to becoming a bankable movie star, he’s also built an entertainment and business empire… and last month, at 44, he was awarded the Mark Twain prize for American humor – as close to a lifetime achievement award as you can get. Hart’s comedy isn’t particularly controversial, it’s conversational with a lot of cursing thrown in. He tells revealing stories about his wife and four kids, his embarrassing insecurities and his many shortcomings. On stage Kevin Hart is an open book, but when we sat down with him… on one topic at least, he was a bit hard to pin down. 

Anderson Cooper: GQ said you’re 5’5″, the L.A. Times says you’re 5’4″, and some other place said you were 5’2″. 

Kevin Hart: Well, that place is b******t. (laughter) GQ finally got it right.

Anderson Cooper: 5– 5’5″?

Kevin Hart: 5’5″.

Anderson Cooper: All right.

Kevin Hart: Five foot five. Like, with a shoe on, like a sneaker. Now, if I put a boot on, I can get to 5’5.5″.

Kevin Hart has been telling tall tales about himself on stage for more than two decades. 

Kevin Hart: It’s talking about the things that you aren’t afraid to laugh at about yourself. I’m really confident that the laugh that I’m getting, you’re not laughing necessarily at me, as if I’m a joke. You’re laughing at the experience. I’m giving you an experience through a story that is relatable. And more importantly, I’m saying things that other people just don’t have the heart to say.

Anderson Cooper: I mean you told a story about your wife watching tall people porn.

Kevin Hart: Yeah. (laugh) Yeah, he was taller than me. (laugh)

Anderson Cooper: That was your main issue?

Kevin Hart: Yeah. “Why is he so tall? (laugh) Is that what you want?” That was real, we had a real conversation off of that. “Is that what you’re lookin’ for? If your search starts with tall.

Anderson Cooper: Is that– you can’t– you can’t fix that.

Kevin Hart: Yeah, no, I can’t fix that. We got a problem. (laugh)

Kevin Hart (in Irresponsible) One of the sites wasn’t even porn. One of the sites was a bunch of tall men being active. They were changing lightbulbs, putting s**t on shelves, hanging paintings. What kind of sick s**t is this? What the f**k is this? She was like, “what, you can’t do none of that stuff, I like that stuff.” 

Hart is the highest-grossing comedian today. He sells out arenas around the world… and the occasional football stadium.

When we first met him in January at his offices in Los Angeles, he was working on new material for an upcoming comedy tour. 

Anderson Cooper: To do an hour comedy special, how long does it take?

Kevin Hart: For me to really work on a set, eight to nine months.

Anderson Cooper: Are you sitting in a room with your team?

Kevin Hart: No.

Anderson Cooper: No.

Kevin Hart: I’m goin’ back to ground zero.

Anderson Cooper: Just com– small comedy clubs, trying it out?

Kevin Hart: Small comedy clubs, rooms. I got two guys, Harry Ratchford, Joey Wells. They act as my writers. And what they do is they grab my material as I say it. But you can’t write it down for me. Like, I don’t– I don’t like the long jokes and long sentences. So it has to be in bullet points. Travel, bad, (laugh) bad travel. Why bad travel makes me drive. Driving, good versus bad. Everything has a good and a bad. My rule is when I get on stage, I would much rather have the dismantled picture in my head of kind of what I think it is, and it not be good, then figure it out in real-time and walk off stage and go, “It was somethin’ there.” 

A few hours later 3,000 people showed up in Pasadena, to hear Hart figure out his new jokes onstage. Everyone had to hand over their phones. 

Before he began, Hart explained why.

Kevin Hart (on stage at Pasadena Civic Auditorium): Like 90% of what I’m going to do tonight I feel like is really good, the reason why I took your phones is because of the other 10%. Right? Like just in case. Just in case some of it’s not, you don’t have no proof. 

We agreed not to record any of his routine either, but backstage we found his collaborators Harry Ratchford and Joey Wells taking a lot of notes. 

Anderson Cooper: How was this audience?

Kevin Hart: This audience was great. Great. Like, you could feel– the laughter never stopped. That’s the beauty of the theater. The theater lets you really feel the highs and lows of a set.

Joey Wells and Harry Ratchford along with comedians Will “Spank” Horton and Na’im Lynn are among Hart’s closest friends. They’re also known professionally as the Plastic Cup Boyz. 

Anderson Cooper: What are you actually looking for when he’s on a stage and telling– a joke? What notes do you have?

Joey Wells: Harry’s always structure.

Harry Ratchford: Yeah.

Joey Wells: “We should put the joke here and move it around.” And for me, I’m always just like how can he be just a little funnier? He might get a standing ovation. I’d go that was great. That was great. What if you tried this? 

Spank and Na’im have known Hart since he was a teenager growing up in a rough neighborhood in North Philadelphia. 

Anderson Cooper: Was Kevin always as confident as he is today?

Spark Horton: Yes.

Na’im Lynn: I mean, it was perplexing in– in the beginning. Like, “Why does this little ugly dude have (laughter) this much confidence?” I didn’t get it.

Spark Horton: North Philly, North Philly.

Home movies his mom made show Hart was always the family entertainer. He lived in a one bedroom apartment with his brother Robert and his mom Nancy Hart. She kept a close eye on Kevin.

Anderson Cooper: She planned every moment of your day?

Kevin Hart: Every moment. I had no free time. After finishing my homework, I had to get to swim practice. Me and my mom would walk home from practice. The homework that I was supposed to do beforehand, she would go over and check, and end up making me redo it, ’cause nine times out of ten, I rushed through it just to get it done. She would then make me read. And I would skip pages, not expecting the quiz of the book to come on the back–

Anderson Cooper: (laugh) Which she would give you?

Kevin Hart: –half, which she would give me when I said I was done. And then–Anderson Cooper: Do you–

 Kevin Hart: –she would make me read it again.

Anderson Cooper: Do you credit her with the drive you have?

Kevin Hart: Absolutely. Absolutely.

His mom also kept Kevin’s dad – Henry Witherspoon – at a distance. He was in and out of prison and addicted to drugs, which Hart talked about in a 2011 standup special called “Laugh at My Pain.”

Kevin Hart (in “Laugh at My Pain”): I was into weird s**t like spelling bees, debates. Now here’s the thing, my dad would show up to my events and treat them as if they were athletic events. First of all, you can’t cheer for no kid at a spelling bee. It’s a spelling bee. It’s quiet, I’m focused. I’m in the middle of spelling a very difficult word. My dad shows up late. Busts through the back door high as hell making cokehead noises, alright. Once again, I cannot make this up. Alright, this is all I heard. I’m in the middle of spelling some s**t. Out of nowhere all I heard was: alright, alright, alright. Yeah!”

Anderson Cooper: The actual details of stuff he did are really heartbreaking.

Kevin Hart: Yeah

Anderson Cooper: And yet, you tell it in a way that’s funny. Is it heartbreaking to you?

Kevin Hart: No. Because-

Anderson Cooper: It must have been, at the time?

Kevin Hart: I see it for what it was. But as a kid, that’s dad. By the way, in my environment, that’s the norm. It’s normal to see a parent drunk, or whatever. 

Anderson Cooper: Your dad, even in the depths of his drug use, he wanted to see you and your brother.

Kevin Hart: Absolutely, there was a period where he disappeared. I didn’t see him in a long time. And I saw him on the subway. And he was in bad shape. And I was like, “Dad.” He turned around and saw me– and doors open, my dad walked off and– and ran. Later told me, “I ran ’cause it just hurt me for you to see me like that and that was one of his key factors into going and getting help.” 

Hart was eventually able to help his dad get clean before he died in 2022. 

Kevin said his father loved to hear the stories he told about him in front of thousands of people… 

…but when Hart started doing standup at 18, he struggled to find places to perform. 

Anderson Cooper: You would take gigs wherever you could get them.

Kevin Hart: Like you’re talking bowling alleys. You’re talking cabarets, strip clubs.

Anderson Cooper: Is there a lot of comedy in strip clubs?

Kevin Hart: No, Anderson. Why you think there’s a lot– no. I don’t know who thought that comedy and strippers mix. But I remember one of the most heartbreaking moments for me on stage is like in the middle of my set.

Anderson Cooper: This was at a strip club.

Kevin Hart: And I remember hearing this lady go, “Oh, baby.” (laugh)

Anderson Cooper: After you told the joke?

Kevin Hart: “Oh, baby.” Like– like, basically so disgusted and heartbroken that this is what I chose to do with my life. 

Hart thought he was about to make it big when he shot a sitcom for ABC called the “Big House” in 2003.

The network flew him out to the upfronts to present the show to advertisers and the media. 

Kevin Hart: I’m next to walk on the stage so they can announce “The Big House.” You’re the guy with the microphone that’s backstage managing. This is what I see. He’s right here. I’m with him. Alright. I’ll tell him right now. Alright Kevin. Hold up one second. They just said they’re not– they’re not gonna go through or pick it up. Somebody should be back here to talk to you shortly.” What does that mean?

Anderson Cooper: The guy with the microphone is telling you that your series is not being picked up by the network?

Kevin Hart: Not– not– the network exec, not–

Anderson Cooper: It’s not the head of–

Kevin Hart: –not the head of–

Anderson Cooper: –not the CEO of Disney coming out and saying, “Hey”–

Kevin Hart: No, no. No, no. A guy name Barry in the back, holding the curtain.

Anderson Cooper: It was only because of that rejection–

Kevin Hart: I don’t want to feel that. I don’t like that you gotta hire me when you’re ready. You’re saying that my career is basically determined off of the needs of people that I don’t know and that I don’t talk to? (laugh) I might be sitting here all day if I don’t go grab it and I don’t go make what I feel should be mine.

And that is what he did. He started a small production company, now called Hartbeat, and began making his own hour-long stand-up specials. He also marketed himself relentlessly through social media…

…Hollywood studios took notice. 

When he was picked in 2018 to host the Oscars it seemed like a highpoint in his career. 

But then comments he made about gay people years earlier onstage and on twitter caused controversy. 

Hart stepped down as the Oscars host.

Anderson Cooper: Initially you didn’t apologize. Later on you did.

Kevin Hart: Well, later on the understanding came from the best light bulb ever. Wanda Sykes said, “there’s people that are being hurt today because of comments like the ones that you made then. And there’s people that were saying that it’s okay to make those comments today based off of what you did then. It was presented to me in a way where I couldn’t– I couldn’t ignore that. So in those moments of despair, great understanding and education can come out of it if you’re given the opportunity.

These days it’s hard to keep track of all the businesses Hart has a hand in. The weekend we spent with him he was in constant motion and promotion… starting with his daily pre-dawn workout. 

Then he was off to Walmart to publicize a nutrition supplement company he owns. 

He’s also got a fast-food chain, a tequila brand, and a $100 million venture capital fund. 

And Hartbeat, that little production company he started, is now worth more than $650 million.

Kevin Hart: I’m no longer just a comedian. I’m an investment. I’m a studio. I’m a partner looking for partnerships. Work for hire is not in my best interest if it’s a one and done situation. 

That means the endless stream of movies, shows, podcasts, and commercials Kevin Hart pops up in… chances are Hartbeat is making money off them too.

Anderson Cooper: Are you a billionaire yet?

Kevin Hart: None of ya business… You tryin’ to get me robbed? (laugh) You tryin’ to get me knocked–

Anderson Cooper: But, I mean, look, y–

Kevin Hart: –in the… the head.

Anderson Cooper: I mean, you will be a billionaire.

Kevin Hart: I mean, hopefully. And– even if I don’t or if I’m not, I think the better side to what I’ve done is create what can become the new norm for other people in the business of funny, for other people in the business of entertainment, right? Not just being a part of the business, but learning and understanding how to be the business. 

Produced by Nichole Marks. Associate producer, John Gallen. Broadcast associate, Grace Conley. Edited by Jorge J. García.