Written by A.R. Shaw
Images by Hannibal Mathews and OMG Booth for Steed media service

It didn’t take long for Kevin Hart to turn his cover shoot with rolling out into a party. Moments after Hart arrived at PPR Studio, he morphed into the pseudo rapper Chocolate Drop. Jay-Z and Kanye West’s Watch The Throne album blasted from the studio’s speakers as Chocolate Drop nodded his head to the beat of “Who Gon Stop Me.” While staring into ro’s videographer’s lens, Chocolate Drop rapped a short nonsensical freestyle that left our entire production crew doubled over with laughter and gasping for air.

But Hart didn’t crack a smile. Remaining in character he yelled, “Real rap raw! I got crazy bars, kid. Somebody needs to sign me today, yo!”
Hart portrays a struggling rap artist searching for a big break with ease. In reality, he’s one of the most successful comedians on the planet. His gift for witty observations on life took him from the mean streets of Philly to the upper echelon of comedy. Hart’s big break came after Dame Dash discovered him performing stand-up at a club in New York. Dash and Jay-Z later recruited Hart to be in the Roc-A-Fella-produced film Paper Soldiers.

After gaining more notoriety in the satirical film Soul Plane, Hart released several stand-up DVDs that solidified his place as a topflight comedian.
But Hart’s not satisfied with just being one of the funniest men on the planet. While most of his peers concentrate solely on perfecting their jokes, Hart builds his brand by partnering with corporate sponsors such as Ford and Brand Jordan.

Hart chatted with rolling out shortly after Hannibal Mathews and OMG Booth photographed him on a smoldering Saturday afternoon in late August. During the convo, he delved into his rise to fame, his new film ventures and how he broke Eddie Murphy’s record for “Raw” by grossing $1.5 million in two days of ticket sales during his “Laugh at My Pain” comedy tour.

You can laugh, but Hart’s tenacity and knowledge of the bigger game is no joke.

There are a lot of funny guys who make us laugh at barbecues or at the barbershop. But there aren’t many who can make a career out of telling jokes. When did you realize that you could do this professionally?

I’ve always been silly and the life of the party. But I came into the reality when I was a sneaker salesman. My co-worker gave me the idea to go to a comedy club. My first time on stage, I wanted to s–t on myself. The lights were on me, people were staring at me and they wanted to laugh. It took a second for me to realize that I had to start talking. Once I got over the initial shell shock of being in front of the lights, it was easy. I eventually won six times in a row.

Laugh at My Pain will be released in theaters this week. How long does it usually take you to write material?
It takes me about a year to write my jokes. I go to comedy clubs and test my material. I continue to set a high bar for myself. My first stand-up comedy special sold well and my second stand-up film [went] six times platinum. So I knew my next special had to be better than that. I was able to perform in front of over 15,000 people at Nokia Theater in Los Angeles. It eventually broke the record that was held by Eddie Murphy’s comedy tour, “Raw.”

How did you get involved with the film Think Like a Man?
Steve Harvey is a good friend. Will Packard and I met and he said that he wanted me to star in the film. It’s a smart, urban film. So they put together a great cast. We just finished shooting. It took two months to film.

When we think of comedy, we only think about enjoying the jokes. But with the recent troubles of Katt Williams and Dave Chappelle’s hiatus from the business, are there hidden pressures of being a comedian?
A lot of those guys didn’t really lose their way. The industry and media has a way of flipping things and making it into what they want it to be. No one knows what’s really going on with Dave. No one really knows what’s going on with Katt. At the end of the day, they are two talented and funny dudes. Given the opportunity, they can continue to be funny. When it comes to pressure, you are your own judge. I don’t take the word pressure seriously. This is what I chose to do, so I don’t pay attention to pressure.

Are there any drawbacks from constantly being in the limelight?
This is the life I chose. I don’t mind my fans requiring my time. So when I’m on the street, I’ll stop to take pictures if necessary. The best thing about being in the limelight is realizing that you have an effect on people.

What are your thoughts on President Obama?
I think Barack Obama is doing what he’s supposed to do. People expect an overnight change. George Bush was in office for eight years and messed up a lot of s***. President Obama is trying to repair what he can.

If you were president, what would be your first agenda?

If I was president, I would buy all of the pants in the world. I would keep them in the White House. And no one would be able to wear pants because I’m the president.

You discuss relationships a lot. Tell us how broke dudes can date supermodels?
You take ammonia and you put it in a cloth. Act like you’re going to hug her and put it over her mouth real fast. She’ll be knocked out and you can take her with you. Technically, that’s a date. It’s not legal, but it’s somewhat of a date. But seriously, you can try be funny. Being funny can get you a long way in the relationship department. Just make someone laugh.

How does a woman know a man loves her?
That’s difficult, because it takes a guy a long time to get to that level. Some women can mistake consistency and companionship as love. But it’s not sometimes. Guys can like your company and be around you for a long time. And eventually, some guys may move on or get distracted. It’s human nature. But when men get to a certain age, they mature and realize what’s important in a woman. That age, for men, is about 56. You’re not in love until your 56.

When it’s all said and done, what do you want people to say about Kevin Hart and your place in comedy?
I’m becoming a mogul. I’m 32 and I’m a CEO. I have my own company. I’m writing, producing and I will be starting my own film projects. Look at what Tyler Perry has done and what Ice Cube has done. They took their own money and invested in themselves. It’s about making history. My goal is to be a legend in comedy. My goal is to be mentioned with Richard Pryor and Eddie Murphy. That’s the best thing in the world. I want to succeed on all levels.

A.R. Shaw

A.R. Shaw is an author and journalist who documents culture, politics, and entertainment. He has covered The Obama White House, the summer Olympics in London, and currently serves as Lifestyle Editor for Rolling Out magazine. Follow his journey on Twitter @arshaw and Instagram @arshaw23.