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A Conversation with Kevin Hart

By Brennen Matthews

Introduction by Olivia McClure

Photographs by Dennis Leupold

When Kevin Hart isn’t busy touring the world, performing stand-up comedy or shooting his next blockbuster, he’s most likely on dad duty for his children. He could also be managing his intense fear of reptiles or adding to his extensive automobile collection.

Given the veracity of his personality and life experiences, Hart often looks to one obvious source for comedic inspiration — himself. Hart uses self-deprecation to his fullest advantage, observing the implications of race and masculinity, as well as his dysfunctional family history and shorter stature. Hart is only 5’4 but has a giant personality and a huge amount of talent to back it up.

Far from the image of a prototypical Hollywood progeny, Hart, born and raised in Philadelphia, and his older brother Robert, were raised by a single mother while his cocaine-addicted father spent the majority of their childhoods in and out of jail. With plenty of life experience behind him from a young age, Hart naturally adopted a humorous mindset to cope with life’s chaos and uncertainties. Now, he shares his unique perspective with audiences around the world.

For Hart, whose previous characters relied heavily on his comedic presence, his role in director Neil Burger’s 2019 The Upside, signifies a step into uncharted territory — and it’s one he was more than willing to take on.

In the film, Hart trades in his typical comedic persona for one of a more dramatic hue. He portrays recently paroled convict Dell Scott, who forms an unlikely friendship with wealthy quadriplegic Phillip Lacasse, played by veteran actor Bryan Cranston.

Considering his long list of achievements, it can be difficult to imagine Hart as an aspiring comic operating under the name “Lil Kev,” jumping between various comedy clubs on the East Coast, vying to get his foot firmly in the world of stand-up comedy. It’s even more difficult to believe disgruntled audience members used to boo the now-legendary comedian offstage at early gigs. It’s safe to say that fame often comes at a price. In Hart’s case, this price has surely been paid off.

You did a great short video with David Beckham for H&M called The Roadtrip. Are you and your family a “road trip” bunch? Do you travel very often by road together?

Not much by road. We travel — we are a vacation family. We love to go to different destinations and, you know, create our moments — create things we can hold onto. So the holidays are a big time for us, during Christmas, spring break and during the summer, and we try to go to very different places. But we’re definitely big with the vacation mindset.

Where is your favorite place to vacation in the United States?

We love Aspen [Colorado] around the holidays. I don’t think there’s anything better. It’s just festive — the snow brings a different element to the environment. Of course, the kids love it because they love snow and, you know, just the whole cabin-like feel, depending on where you are or where you’re staying. It just feels like Christmas, so it’s something that I enjoy, they enjoy, the wife enjoys it, so we’ve been very consistent with making that our thing. It’s a Hart family vacay every year.

So, do you ski?

Not well, but I’ll get on them. Not to say that it’s the smoothest thing you’ve ever seen, but I’m out there with my kids, you know, and if they want to do it, I’ve got to do it. So there is no halfway moment.

You have been a car enthusiast and collector for some time now. Where did it start?

Well, when you’re a man and you start to get older, you start to realize that you’ve got to get hobbies. It’s things that you can throw your attention to, you know, that are home-based.

There’s a point when you come to realize that running the streets and being out all the time isn’t what life is about, and you find other things to peak your interests. And for me, it’s cars. You know, I love the fact that these are things being built — things that I can start from the ground up and treat as projects and I can pass onto my kids when they get older— that they can attach to their father and know how much love and time and energy I spent in purchasing these various things. So, there’s a lot that goes into it. I’ve developed a love over the years, and I don’t see it calming down anytime soon.

What was the first car you ever acquired for your collection?

The first one that I’ll say is a good one: my SLS Mercedes-Benz. It’s a 2011 SLS with the gullwings.


And you have a ’66 Pontiac GTO as well?

Yes, sir.

Do you ever drive these cars?

I drive them all.

If you were going to do a road trip down Route 66 — a proper across-America two-lane highway — which car would you take?

The best car for me, right now, is my Ferrari.

So, you want to move fast?

No, I think that’s the most comfortable ride. I mean, there are a lot of choices that I can make. So, I could have said my Corvette, there’s a ’67 that I have. I could have said my Mustang, my Eleanor — that’s another good ride. That’s a strong engine, so to deal with that noise the whole way would be a lot. My Bronco — there’s a ’67 Bronco, which would be a fun ride. I’ve got a Jeep Wrangler, and I’ve got a Rubicon now. The Rubicon is actually an off-road one, which would be good.

Actually, you know what would be a good ride? The Maybach. I could just enjoy the scenery from the back because it has a dual sunroof.

I can put my kids in the Sprinter and make it a family trip. Because the Sprinter, I basically customized to fit our needs from the inside, so whether it’s playing video games or watching movies or eating various fruits out of the cooler — we can do all that stuff.

No — I’ve got it! My wife’s Bentley. That’s the coolest car.

I didn’t expect it to be. Like, when you close the door, the seat belt automatically goes on. You don’t even have to do it. Yeah, it’s pretty dope. Those are the little tricks they show you to get you to buy it.

If you were going to do a road trip, which celebrity friend would you bring with you?

Will Ferrell. One hundred percent, Will Ferrell. Will is funny non-stop. You know, he’s a guy that loves bits, loves improv, and I’ve spent a lot of time with him, and after spending time with him, I’ve found our comedy back-and-forth is not just funny, but special. So, the constant playing out or acting out of bits is just — carrying on and on — I feel like if you’re going to be in a car, you’ve got to be in a car with who you laugh with [and] who you’re not going to get tired of, and I don’t think I would get tired of Will at all.

When did you realize that you were funny?

I would probably say at the young age of 11. It’s at 11 when your personality kicks in and your friends — your friendships start to grow. And people also wanted to be around because they’d say, “Kev is funny,” or “we want to be with Kev,” or “we want to ride with Kev and be on the bus with Kev.” And people started to laugh, so it started to click with me that the funny presence that’s associated with myself is one that’s welcome. I like it, and it’s something that I’ve really enjoyed.

How does your family feel about you including them in your stand-up routine?

They have no feelings because it’s not malicious. It’s all told from my point of view, you know? Self-deprecation is what I love. It’s what I do very well, so it’s all told through a lens that comes back to me, and you’re laughing at my response or my actions or my reaction from something involving other people. So, no matter what it all comes back to me.

Do you see any of your kids following in your footsteps?

My daughter has a very strong personality, I would say. She for sure has it. My son is a late bloomer. I see it starting to come with him and, you know, my youngest, of course, I can’t see nothing yet because he’s not talking. Mainly with my oldest, my daughter — she’s 13. But her personality is just amazing — you know, life of the party, center of attention, funny, loves to tell jokes. She definitely has it, for sure.


You seem to be very close with your children. What’s your favorite part about being a dad?

My favorite part about being a dad is that you get to watch these little lives develop into adults, you know? You get to really see your imprint. When you’re an active part of your child’s life, you get to see them slowly mold into mini versions of you, and they’re literally parrots. What you say is what they’ll repeat, what you do is what they’ll repeat. So, for me, it’s about being present. I learned the mistakes that were made from my dad with me coming up, and I know where there should have been a lot of time spent, but there wasn’t, and it left a sour taste in my mouth. It’s a crash-course education of what I have to make sure I do better when I have kids, and now that I have them, I understand that the most important thing you can give is time. So spending time with my kids, just being present, is the most important and best thing about parenthood in my mind.

When you were starting out, you hit a couple of bumps with non-appreciative audiences. What was going through your mind in the early days when your work was not being embraced?

I mean, look, at that time, you’ve got to understand that it’s all a learning experience. You know, you’re going through the good, the bad and the ugly to get an understanding of just that. Those experiences only make you better. They only make you stronger. So, you have to understand that a lot of people quit because [it’s not] easy. Not many stay put and fight through it. The ones that push through are the ones that end up making it because they have the will and ability to stay through it all. That’s my opinion.

Were there times when you thought, “I’m done with this”?

No, I was pretty positive. I never contemplated quitting or turning my back on it at all. It was always, “This is what I’m doing, this is what I chose, this is my life, this is what I’m investing all my time and energy into. I’m not turning my back on it.”

Was there any particular moment in time, or with a certain project when you felt, “Wow, I made it! Now I am successful”?

I mean, look, to date, I still don’t have the feeling like it’s over. I just feel like everything — I guess you could say I feel a fulfillment knowing all your hard work is paying off, but where you’re still putting in a crazy amount of hard work. Then, that’s your way of saying, “You know what? Not only is my hard work paying off, but it only gets better. It only continues to grow. How much bigger can I make it? How much further can I get in this?” You know, with that being the case, it’s more of a motivating factor to me. It’s not necessarily “made it,” it’s just that I made monumental steps on a road that’s a long one, — that’s full of many goals that are still trying to be achieved.

Do you have any projects you’ve done so far that stand out to you as your favorite?

As a comedian, nothing’s ever going to surpass stand-up comedy and my tours — that’s always going to be number one. Outside of that, I definitely have to say The Upside is very high on that list, just because of who I got to work with, the type of movie that it is, and I love that I took my time in doing it and finding the right project. I would say right now, this would be my favorite film.

You have a lot of scripts coming your way, but you took your time with this one. What drew you to The Upside?

The material within itself; the opportunity to play an individual who went through hardship in life and is trying to do the right thing and make it out and has the feeling that he’s being held back because of, not just race, but because of the fact that these people have no will to go and address situations correctly. I like that it’s about a guy who feels that he’s being held back by a system and by “the man,” but [then] realizes that “the man” isn’t as bad as he thought he was and that just because you have money doesn’t mean you have everything. And I also give that man a life lesson in that having that happiness is a choice and that he can still make the choice. We find good in one another. We find reason to live and love through the friendships that came across unexpectedly.

And for me, playing a character that can address a kind of situation within the times that we live in — be grounded, be authentic, be real and act as a voice — it just made sense. It’s a time for me to do it in my career because it’s so different from anything I’ve done.

There are some very funny scenes in the picture. Were there any in particular that were really hard to get through because of people laughing?

The catheter scene was probably the hardest to get through.

That was a classic scene for sure. The other scene that really stood out was when Dell, your character, got tired of waiting and burst in for his interview.

That scene was a great scene because it was a scene where you got to see the difference in Dell from everybody else that Phil’s been dealing with throughout the day, throughout the week. You know, interviewing for a position and everything sounds the same, everybody’s kissing his ass. And I come in without knowledge of who he is or what he has, and I’m speaking to him in a way that he’s never been talked to before. And that was interesting to him because that’s something new, and I became a person of interest and that’s when I decided, “Ok, I want him.” It was a sabotage move without the feeling or expectation that he would end up liking me. Phil just wanted to go against the grain and piss off everybody else around him by bringing somebody that was not going to qualify for the position.


The Upside showcases the natural cultural tensions between your character, a black ex-con from an underprivileged background and Phil, a white, billionaire who is now a quadriplegic, but who has been very successful in life. Do you think that racial tension has reduced or gotten higher in today’s America?

Well, I don’t think racism ever went anywhere. It’s always been existent. Right now, you’re just seeing the people who were hiding it for so long. They’re now being bold enough to express. You know, in times like these, this is where the good has to overpower the bad, and I think the best way to do that is to give you good material to watch, things to see. This movie acts as just that. You know, when you’re looking at two different sides of the spectrum, and you’re addressing problems of race and being vocal about it ... from Dell’s perception of a white man and what a white man has and what a white man should be, and Phil’s perception of a black guy who’s been in jail and what he’s done and what he’ll do for the rest of his life ... When you get to see these two opinions that are formed, you realize the problem that is formed today. And that’s that we’re so in love with assuming, that we have yet to set out what the true problems are, and have a true understanding to what the problems are, on both sides. Because if we did it properly, we’d have understood that we could have a conversation accordingly and help move in a direction that appeals to both sides, to where you feel like you’re being heard. But I feel like right now, there’s a lot of yelling and not enough listening and understanding, which allows the problem to just continue to grow until it can be resolved.

You made a decision a while back not to include politics into your stand-up. Moving forward, will you still steer clear of politics in your comedy?

One hundred percent. It’s not who I am. What society loves to do is put situations on people who don’t ask for them. You know, I’ve never been a political voice. Because I have a massive following and a large fan base, that doesn’t mean that, out of nowhere, I’ll become a political figure. It’s not who I am. It’s not authentic to who I’ve been. So, you know, in that particular case, you’re damned if you do and you’re damned if you don’t. Because if you do start talking about it out of nowhere, then people are going to go, “Well, that’s not you. You’ve never done it before. Why are you doing it now?” And if you don’t, then you don’t say the right things and it’s not what you should be saying. I’m a comedian, and I feel like, for me, people are choosing to go to comedy shows to step away from the problems in the world today. You can watch CNN all day if you want to hear debates about it, you can watch the news, you can go on social media. It’s a non-stop conversation. When you choose to go to see live entertainment, it’s because you’re looking for entertainment, you’re looking for relief. That’s what comedy is. I’m not going to take that time to divide when I can use it for better and bring people together through laughter. That’s my choice.

You’ve developed a huge following and a lot of success, Kevin. At the end of the day, how do you stay grounded?

The thing is to keep your circle tight. You’ve got to surround yourself with individuals that you really know and that really know you. When you do that, you put yourself in the best position to stay true to yourself and your beginnings, because this can all change overnight, and the one thing that shouldn’t change is your friends and your family. You just can’t lose the perspective of life, and as long as you’re constantly thinking like that, you’re in a good place. When you feel like it’s supposed to be this way, and it’s never going to change, and everybody can kiss my ass, and you better do what I think is right, you won’t last. Because you become part of the problem — a problem where people don’t appreciate the fact that they are fortunate enough to do what they love on a very high level. There’s not a large group of people that can say that, so if you’re fortunate enough to do what you love, then be humble and appreciative enough of it and make sure that you’re a voice of positivity for others around you to understand that, “Hey, you can do it. Work hard. Inspire,” you know?

What’s next for Kevin Hart?

I think the next thing for me now is getting the business of Kevin Hart to catch up to the star. Right now, if you look at the star, he’s accomplished so much and done so much, but I want the business. I want the production company, I want so much to go into that — so much time, energy and effort. So that that’s a company that’s running by itself with or without the involvement of the actor, and that’s a journey. It’s a lot of hard work, blood, sweat and tears that have to go into it, but it will pay off. These are all things that I’m focusing on to get to a place where I feel like I’m progressing, but I just want to see more. I want more.


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