Kevin Hart Built a Comedy Kingdom. Here’s What Else He Wants.

KEVIN HART has a dossier on his business ventures that is a thousand words longer than this profile. It breaks down the movies, TV shows and other productions on the burner for Hartbeat, his flagship entertainment company valued last year at $650 million. Also on the document: Hart’s venture-capital firm. His tequila brand. His restaurant chain with the plant-based burgers and shakes. His autobiographical self-help books. His line of superfood supplements stocked at Walmart. His partnerships with companies from JPMorgan Chase to DraftKings, Audemars Piguet watches to the sportswear line Fabletics, a portfolio that has Hart chirping along in seemingly every other commercial on television.  

All these bullet points and brand names tell the story of his career over the past decade. Hart’s been telling it, too. 

“That’s the business. The business of return,” he says in the default exclamation mode he’s known for. “Sometimes people don’t respect the ROI—the return on investment. I’m a secure investment.” 

It’s 8:30 a.m. and he’s at home in Los Angeles. He got up at 5 for a workout, three hours after his plane landed from a performance in Connecticut the night before. He pauses an interview midsentence when his 3-year-old daughter, Kaori, wanders in—“C’mere, mama! Come give me a hug!”—then completes his thought after the youngest of his four kids moves on. Next up, a 10:30 meeting with Hartbeat employees about the company’s 2024 agenda. 

Lots of comics have morphed into screen stars, but there’s no precedent for Hart’s hyperactive level of entrepreneurism and dealmaking. Same for his self-declared quest to create an empire and become a billionaire. Jerry Seinfeld says Hart’s ability to maneuver in other fields is an anomaly: “Most comedians cannot function outside of comedy. If someone said the word ideation to me, I would just walk out of the room.”

But because of Hart’s blitz into ubiquity, it’s easy to forget that it all started with—and still revolves around—the most basic thing in show business: a man with a microphone, alone on a stage. 

There, Hart is known as an amped-up everyman whose recurring targets are his family members and himself. In his most recent comedy special, last year’s Reality Check, a rant about rampant cosmetic surgery spins into a signature, self-mocking hypothetical: What if famously short Kevin Hart had a procedure to get super tall? 

“I still got the same arms. I didn’t judge it right. Now I can’t put my hands in my pockets,” he says, wagging his limbs, then going tipsy. “I’m 6-6 but I still wear a size 7 sneaker. Now I can’t support the new body. My balance is off. I look like that thing that be at the car dealerships, that air man.”   

Hart’s firepower in stand-up put him in the vanguard of solo comics who can routinely sell out sports arenas and the occasional stadium. Now that part of his trade is coming back to the fore when he accepts the Mark Twain Prize for American Humor at a ceremony scheduled for March 24. It’s the closest thing the comedy business has to a lifetime achievement award, which the Kennedy Center has bestowed on recipients from Richard Pryor to Adam Sandler, another mass-market talent. Hart is the 25th and, at 44 years old, one of the youngest. 
 

Winners and trophies (specifically, a bronze bust of Samuel Clemens) seem like oxymorons in the subjective and cynical world of comedy. But the genre’s elites have validated the Twain prize. They descend annually on Washington, D.C., to fete their friends who accept the award in a televised gala that doubles as a black-tie roast. 

In the endless debates that fans and comedians themselves wage over their personal rankings of the greats, official accolades don’t carry much weight. In this conversation, Hart’s commercial clout gets talked about more than his skill in the craft of stand-up.

Hart’s own opinion is this: Art and commerce should be part of the same sentence in any conversation about his place in the comedy pantheon.

“I do know what I’ve done for the craft of comedy. By that I mean I’ve changed the business of stand-up comedy,” he says. Namely, he leveraged popularity in that realm to diversify into other industries (emulating friends such as LeBron James and Jay-Z) and created a model for other stand-ups, he says. “Whether you’re a fan or not, you have to respect what I’ve done. Point-blank. Because you don’t do it by accident—and you don’t stay here by accident.”

---

LAST OCTOBER, Geof Wills, president of Live Nation Comedy, got a text from Hart. The promoter has done about 800 shows with the comic since signing him in 2009. In 2023, Hart brought in $67.5 million in ticket sales from 82 shows, topping Billboard’s list of top-grossing comedy acts (for the second year in a row). Hart’s message said he was poised for more: “I got a new 30 minutes.”  

That chunk of material started with drop-in performances at small clubs, including the Comedy Cellar in New York City and Flappers in Burbank, California, and had roughly doubled in length for a recent string of shows in theaters. 

At an ornate former movie palace in Providence, Rhode Island, Hart performed for an audience of about 3,000 people. Their phones were in locked pouches to prevent his jokes from leaving the building. He wore vintage white Pumas, tapered Burberry khakis and an ochre sweater with a skeleton design by Japanese label Kapital. A staffer, videographer Kevin Kwan, emerged at a corner of the stage to capture Hart in action and the crowd laughing on camera.
 

Kevin Hart has come a long way since his days working as a shoe salesman. In The One with WSJ. Magazine, Hart discusses growing from comedian to entertainment mogul, what he’s passing down to his kids, and looking up to Oprah, Jay-Z and Tyler Perry. Photo: Rhys Gray

---

The footage would feed Hart’s promotional machine. On Instagram, where he has 180 million followers, a video montage of him performing and crowds reacting was set to a Jay-Z song (“Allow me to re-introduce myself…”). The comedian’s caption hyped the performances, along with that weekend’s release of Lift, a slick heist movie with Hart in the lead and a global push by Netflix behind it. The hashtags: #HustleHart, #ComedicRockStarShit. 

A different part of Hart’s operation was invisible to his online followers and live audiences. As the comedian breezed through seemingly polished jokes in Providence, he was also stress-testing them. When big laughs erupted, he sometimes gazed to his left and grinned. Hidden offstage, watching from the wings, were Harry Ratchford and Spank Horton, two fellow comedians in Hart’s creative brain trust. 

“That little piece of eye contact from the stage is how they know, Let’s jot that bullet point down,” Hart says later. 

​​​​​​

Instead of writing jokes, Hart develops his routines orally. He farms observations and anecdotes from his conversations with Ratchford, Horton and four other friends who have worked with him for about 20 years. Dubbed the Plastic Cup Boyz, they’re a permanent focus group for Hart’s material who also function in various support roles (tour manager, barber) and as a force field against outsiders. They co-star and have writing credits in many of his productions. Members of the Plastic Cup Boyz are the only comedians who open for Hart on tour.  

Moments after the Providence show, Hart still held the red Solo cup he had sipped his Gran Coramino tequila from onstage. Leaning in a doorway in a mural-covered hallway backstage, he said he felt no residual adrenaline rush from the performance. “For lack of a better word, I’m a computer,” he says, now in set-analysis mode. 

“That was a tight 59 minutes. I’m going to get to an hour straight. I’m going to move three to four things, where I want to hear the laughter be as loud as it is in other places. I should be able to feel the laughter from the top to the bottom.” Snapping his fingers, he says, “It’s fun, it’s fun, it’s fun, it’s fun. People look up? It’s been an hour, but it didn’t feel like it.”

This chill confidence is the opposite of Hart’s comedy persona. Blustery self-delusion (as a husband, a father, a man) is the mode he uses to tap into universal experiences in his audience and put vivid body language to work. He’s a trash-talking coward, quick to tell on his friends and retreat from human or animal threats (ostrich, raccoon, gnats, gorillas, a racist dolphin). In the act he’s refining now, he wanted to eye the back stretch of his 40s and beyond, he says, including “my transition as a father, my hope for family growth and gain, the idea of old age.”
 

At one point he tells his audience in Providence, “I’m an overthinker.” It’s a self-diagnosis and also the formula behind his jokes. 

Tickets to his recent shows were labeled “Brand New Material,” a placeholder for the title of an official tour expected to happen later this year. Rather than jet among one-off shows in the cavernous arenas he’s accustomed to, Hart is considering mini-residencies. Instead of 16,000 people in a night, he would play to roughly the same number during a half dozen shows over a weekend in a more intimate theater.  

In the past Hart has emerged on arena stages with pyrotechnics. Now, he says, “I think there’s an opportunity to do something a little more artsy.”

THE FOUNDATION for Kevin Darnell Hart’s comedy is in North Philadelphia, where he grew up with an older brother and a single mother who was as vigilant as his father was erratic. Nancy Hart, who died in 2007, worked at the University of Pennsylvania and packed Kevin’s time with extracurriculars like swim team to keep him out of trouble. She later agreed to pay her son’s rent for a year on the condition he’d go to college if comedy didn’t pan out. Hart’s dad, Henry Witherspoon, who died in 2022, was a drug addict, in and out of prison and rehab. Spoon’s cocaine-fueled appearances in Kevin’s childhood (shouting at a spelling bee like a football game, going commando in revealing sweatpants) would eventually turn into some of the most riotous impressions in his son’s act. 

Another source of future material: Hart’s stature. He was closing in on his 5-foot-4 peak by middle school. “In the beginning, I was tall. Then people started to shoot past me,” he recalls. “That’s when I was like, Oh, shit, this is my reality.”

At 18 he began performing at a weekly open-mic competition in Philadelphia and winning, but it would take years to learn how to translate personal history and vulnerability into a unique comedic voice. That’s what Keith Robinson, a veteran Philly comedian, demanded as he schooled Hart in the business of stand-up. Hart ditched the bad stage name (Lil’ Kev the Bastard) and started accompanying Robinson on round-trip drives to the comedy scene that mattered more in New York City.

There, getting reps onstage was essential for a young comic trying to break in. So was the hazing from other comics. 

“We would put your joke on trial. ‘Kevin Hart, you’ve got to take that joke to hack court,’ ” Robinson says, recalling brutal burn sessions among their tribe, which included the late Patrice O’Neal. 

On a recent night at the cafe above the Comedy Cellar, the cramped basement club in Greenwich Village that remains a center of gravity for Hart, Chris Rock and other heavy hitters, Robinson was waiting to do a set. It’s much the same small world. When Robinson suffered two strokes in recent years, Hart provided financial and other help, he says, as did friends including Amy Schumer and Wanda Sykes, producers of Robinson’s upcoming Netflix special called (wait for it) Different Strokes. 

Hart wasn’t using words like brand and empire when trying to establish himself on the club scene.

“We would’ve kicked his teeth right out of his mouth,” Robinson says with a cackle. “I mean, can you imagine that idiot telling us, ‘I’m gonna be a mogul?’ ” 

Back then, he advised his protégé to put a New York phone number on his résumé so bookers wouldn’t realize he was commuting from Philadelphia. Dave Becky, who has been Hart’s manager since 2000, found out only recently that his client never actually resided in New York. 

THROUGH THE 1990s and into the early aughts, the only way to convert stand-up heat into mainstream stardom was to get on old-fashioned screens. Break out on Saturday Night Live or a network sitcom, get famous, cash in.

Hart failed at this, more than once. 

In 2001 Becky helped get him in a Judd Apatow–produced TV pilot called North Hollywood, playing an aspiring actor alongside pre-fame Amy Poehler, Jason Segel and January Jones. The show didn’t get picked up. 

In 2002, Hart got Hollywood scouts buzzing at the Just for Laughs festival in Montreal, the hottest market at the time for rising comedy talent. He landed his own sitcom, The Big House, a reversal of The Fresh Prince of Bel-Air, with Hart as a rich kid embedded with working-class family members. ABC killed the show after six episodes.

On the big screen, promising roles in both Black ensembles (Soul Plane) and white (Fool’s Gold, a Kate Hudson–Matthew McConaughey rom-com) didn’t cause a pop.

“He was everywhere, but nothing worked,” Becky says. “So what do we do now?”

Hart decided to retrench in stand-up. He wanted to follow the example of respected aces like Rock, whose run of knockout HBO specials made any lackluster movie roles irrelevant. Borrowing a technique from Dane Cook, comedy’s pioneer of DIY internet marketing, Hart amassed a mailing list by asking audience members to fill out info cards that read “Kevin Hart Needs to Know Who You Are.” As Facebook and Twitter surged, he used them to bombard potential fans. And he improved his material by acting on Keith Robinson’s advice: He excavated his personal life as a father of two young kids with his first wife, Torrei Hart.  

Hart’s comedic voice went wide in a showcase produced by Shaquille O’Neal during the NBA’s All-Star Weekend blowout in 2009. His schtick—loving dad who is outrageously judgmental of his kids and everyone else—killed in the celebrity-studded room.

In a bit about a showdown at Chuck E. Cheese, Hart fumed, “We didn’t look successful. My daughter was taking balls to the face. My son was slobbering. I was small. We looked like a f—ing circus act.” When the set turned raw, Hart roped his hosts into the jokes (“Shaq, you ever having sex…”) and the crowd’s laughs escalated into shrieks. The show was a hit on Showtime and sold more than a million DVDs. It was a catapult moment that helped lead to bigger venues and specials, including 2011’s Laugh At My Pain, which Hart self-financed and independently released in movie theaters. Then came movies that actually landed, like 2012’s Think Like a Man and 2014’s Ride Along, with Ice Cube, the first of Hart’s odd-couple roles with famous big men from Will Ferrell to Dwayne Johnson. The crossover continued into kids movies such as The Secret Life of Pets.

---

HART HAS ESTABLISHED an image that conveys “family friendly” despite lots of jokes that aren’t—and despite major personal screwups. 

It works because he has touched on those mistakes in his stand-up material and even his brand-building efforts. Consider Don’t F**k This Up, a six-part docuseries produced by Hartbeat and released on Netflix in 2019. It’s a chronicle of Hart’s career ascent that, by episode 3, covers him cheating on his pregnant wife, Eniko Hart. That happened in Las Vegas in 2017, when she was carrying the first of two children she’d have with Hart. The scandal was public because of video footage and, as the series lays out, an extortion scheme said to involve one of Hart’s former friends.

Don’t F**k This Up also documents how Hart’s handling of a bigger controversy made it worse. When he was announced as host of the 2019 Academy Awards, outcry erupted on social media over Hart’s old jokes about reacting violently if his son was gay. He gave up the Oscars gig within days, but the controversy stayed hot for more than a month as the comedian seemed to toggle between defiance and apology. The series captures the real-time reaction of Hart and mortified friends and staff, including his publicist, who recommends “a humility pill.” 

Hart, who sustained major injuries in a car accident less than a year after the hosting fiasco, looks back on the episode as “a come-to-Jesus moment,” he says. “Sometimes it’s OK to take a step back and to be educated. I got a crash course. It was one that was necessary and needed.”

While gearing up for his official stand-up tour, which will lead to his ninth comedy special, Hart is going into production on a limited TV series called Fight Night, starring with Samuel L. Jackson, Terrence Howard and Taraji P. Henson. Produced by Hartbeat and super-producer Will Packer, the Peacock show is based on a podcast and a true story about an armed robbery in Atlanta during a Muhammad Ali comeback fight in 1970. 

Hart says he’s not concerned about doing too much or wearing out his fan base—“If you let people tell it, I’ve been overexposed for the last 15 years”—nor does he claim to care what the various smack-talkers and eye-rollers say. 

They include comedian Katt Williams. In a recent three-hour podcast interview that seemed intended to escalate old beefs and start new ones, Williams carved out a few minutes to target Hart (along with Cedric the Entertainer, Steve Harvey, Chris Tucker and others), attacking his origin story and accusing him of scooping up demeaning movie roles that Williams himself had rejected. The objectively bonkers video interview went viral, creating a record scratch that turned every head in the comedy world and inspired a Saturday Night Live parody that referenced Hart. 
 

Asked if any part of him actually enjoyed watching Williams sound off, simply as a piece of entertainment, Hart concedes. “It’s just that. It’s entertainment,” he says, then pivots. “If that’s what he fuels himself off, God bless him. Good for him. I hope he gets all that he needs and he wants, and I’m here cheering for him from afar. That’s my real energy. I really mean it! That’s how happy and secure I am with my career and my life.” 

Hart is as ambitious about establishing himself in the comedy firmament as he is about achieving moguldom. Headliners Only, a 2023 Netflix documentary about a series of joint performances for Hart and Rock, traces both their career trajectories. It closes at a Madison Square Garden show with Hart, onstage with Dave Chappelle, presenting Rock with a live goat, a “greatest of all time” symbol four months after the Oscars slap. Rock is the one holding the goat’s leash as the trio poses for a photo, but the resulting image implies that three GOATs are sharing the moment. 

Fans root for Hart’s #ComedicRockStarShit because he also humbles himself in his jokes. Seinfeld says, “It’s like when they put a little bit of salt in the pasta or something. You don’t know it’s there but it changes the flavor. So I think that Kevin’s secret ingredient, personally, is that there’s a pinch of humility in everything he does.” 

For Hart, who has won multiple People’s Choice awards but is used to bad reviews and getting passed over for Emmys and Grammys, the Mark Twain Prize for American Humor signifies an arrival. Kennedy Center president Deborah F. Rutter praised his “iconic characters, inimitable physical comedy, and relatable narratives” when announcing Hart as the recipient. In other words, a master of “American Humor” in the populist sense. 

“He’s not divisive. He’s not political. Everyone feels good. Everyone has a great time,” says Wills, the Live Nation promoter. “Kevin’s like a great pop record.” 
 

One of the funniest parts of Hart’s 2023 special Reality Check is about his misadventures in activism. In 2020, Hart sounded off during the Black Lives Matter uprising via anguished social media posts, and he attended the memorial of George Floyd along with other boldfaced names. He revisits the painful episode in the special through his lens of extreme self-deprecation. He describes the initial rush of public support he felt for his posts on social media (They “called me a Black king. Never been called a Black king before. Shit went right to my head”). Then came the realization that he was totally out of place at the memorial and demonstrations. “Everybody’s got on activist wear. They wearing all black. I’ve got a goddamn salmon-colored V-neck on with some khakis, looking like Carlton in his prime.” 

The bit, which doesn’t include the name George Floyd, is a balancing act that epitomizes how Hart has defined himself as a crowd-pleaser, not a button-pusher. 

“The joke came from me realizing, this isn’t what I do,” he says, unpacking the evolution of the routine. During the real-life demonstrations, “there was a moment where I was like, what the f— am I doing? Let me go sit my stupid ass down. These people are out here and fired up. I’m not ready to be on that front line on that level. I want to be supportive but I don’t have that thing. So let me make sure I check myself,” he says, adding that, “when it comes to my culture,” his support plays out in institutional ways, such as funding college scholarships and donating to Philadelphia schools. 
 

In conversation, Hart doesn’t talk about his stand-up as art or somehow separate from the many roles and ventures he has his hands in.  

“It isn’t just about the ability to tell the joke. It’s about the ability to make the joke lead to the TV, the TV to the movie, the movie to the ownership,” he says, ticking off other parts of his business portfolio before circling back to stand-up. 

“The jokes,” he says, “acted as my door to get to the things that I’m really good at.”

Write to John Jurgensen at John.Jurgensen@wsj.com
This article appears in the March 2024 issue of WSJ. Magazine.