Diplo Is Workin' 5 to 9
5:00p.m. Charlotte, North Carolina.
The personal photographer is in the trunk.
Diplo is riding shotgun. I'm squeezed into the back seat next to the rest of his crew, about to begin the longest night of my life, which is just a regular night for Diplo: three shows in two different states, the Saturday before Halloween, a holiday that's grown from an evening when children beg for free miniature candy bars into a weeklong bacchanalia for adults dressed in Chihuahua-size polyester costumes. Halloween for Diplo is like tax season for accountants, if accountants had groupies and chartered private jets and were constantly shirtless in public. The plan tonight is to start here in Charlotte with a 9:30 p.m. set and end sometime around 6 a.m. after a performance at a Miami strip club.
“Holy shit, that's insane,” our driver, Jeff, says when he hears about the schedule. He slams the gas pedal unexpectedly and his luxury SUV careens forward at roughly the speed of sound.
Jeff, I should mention, is Jeff Gordon. As in Nascar legend Jeff Gordon. And, as it turns out, big Diplo fan Jeff Gordon. When he heard Diplo was coming to town, he invited Diplo over for a personal tour of the Hendrick Motorsports team headquarters, a sprawling operation where they develop top-secret engine technology and sell souvenir Hooters race car T-shirts. The two met at Madonna's Oscar party a few years back. Then Jeff Gordon was at Burning Man, waiting to watch the sunrise over the playa in his fuzzy Burning Man hat, when he looked over and, what do you know? There was Diplo, getting ready to DJ.
Diplo flew here from an all-nighter in Saint Louis, though you'd be forgiven for thinking he arrived on horseback from the 1970s. He's wearing a denim Wrangler shirt, flared black jeans that give way to beige snakeskin cowboy boots, and sleazy orange-tinted glasses. His dirty-blond hair hangs to his shoulders, and a single gold front tooth twinkles away, demanding a blade of grass to chew.
The tooth follows you around the room like the Mona Lisa's eyes. The original got knocked loose in a fight when Diplo was younger and eventually turned gray, and then, by the time he had to get veneers, he figured, what the hell, why not go for gold? “I don't have a job, so it didn't really matter,” he says, before amending his statement slightly. “I'm doing a country album, so I think having a gold tooth is fine.” That project would be Thomas Wesley—Diplo was born Thomas Wesley Pentz but goes by Wes—an alter ego that has him making EDM-laced country ballads with Cam, Morgan Wallen, and the Jonas Brothers. If his outfits are any indication, he's approached it with the intense focus of Daniel Day-Lewis preparing to play Abraham Lincoln.
We walk through an unassuming door to find ourselves inside a Narnia of a private car collection, with dozens of gleaming classic Corvettes and Optimus Prime from the Transformers movies. At the center is a bronze statue, about the size of a small toddler, of the late inventor of some kind of engine proudly displaying his legacy in his outstretched arms.
“When I die, guys, I want one of those,” Diplo jokes, pointing at the statue. This kicks off a debate about what a miniature bronze Diplo would be holding. A Grammy? He has a few…but definitely not. The SD card on which he stores all his playlists for DJ'ing?
“No, man,” he responds, his gruff voice taking on an ironic Valley Boy lilt. “I don't want to be defined by that.”
How exactly to define Diplo is difficult, because there's no figure in pop culture quite like him. He's a superstar DJ and a sought-after producer and a songwriter and a record executive and even a model. But what Diplo is best at is being Diplo. His public life is so ridiculously over-the-top—filled with nonstop intercontinental travel and hordes of twerking women—that it inspired an entire mockumentary TV series where Dawson from Dawson's Creek plays a hapless version of him. He's more brand than man at this point, but if other brands worry about oversaturation, the Diplo strategy is to do everything, everywhere, all the time. At one point when I'm with him, his publicist receives an email asking if Diplo wants to appear on The Price Is Right, and he answers with the same immediate no-brainer yes that most people would reserve for a free trip to the moon.
As a DJ he rode the EDM boom to the top and held on after the bubble burst, touring about 300 days a year and racking up a reported $25 million net worth as of 2018. When he's not producing hits with Beyoncé or Justin Bieber or Usher or Madonna, he's scouting the globe for the next big Nigerian rapper or Syrian wedding singer. (Even if, as he admits, “I can't play very good music. Put me on a piano and I can't hold a note.”) He's worked in so many genres—electronic, house, hip-hop, dancehall, Brazilian baile funk, Angolan kuduro, and now country—that he's practically his own genre. Try to keep track of his current projects and you'll end up like a TV detective uncovering a vast conspiracy on a bulletin board tangled with pushpins and string.
If you ask some people, what Diplo is also the worst at is being Diplo. His critics will say he's an obnoxious EDM bro who hijacks other cultures' music and has been known to pettily hit back when called out for it. Either way, Diplo has had singular staying power in an industry where careers are notoriously short, where cool and cachet are instantly mutable. At 41, he's still playing to audiences half his age and is more inescapable than ever. He insists he's still having fun, but besides, Diplo's selling something more enticing than fun: brazenly doing whatever the hell you want. And if anyone can't quite understand how he's outlasted himself, it's Diplo. “I'm on borrowed time,” he tells me. “I can't believe it's still going on.”
Jeff Gordon drops us off at the hotel, where Diplo is planning to use a sliver of downtime to work out. But when his outdoor set is pushed up an hour because of impending rain, everyone jumps into motion again. Diplo changes into a BlackCraft Cult T-shirt and denim coat and grabs a cowboy hat. Jeff Gordon rushes back, in a Rolls-Royce this time, to personally shuttle him through downtown Charlotte, now teeming with a zombie invasion of costumed young people drunk on $12 bottles of raspberry-flavored vodka. I'm in a black SUV behind them, and when we idle at a stoplight, I see a woman, dressed as a medieval wench, recognize Diplo and bum-rush the passenger-side window of the Rolls-Royce to yell something at him before sprinting off, scream-giggling. When we get to the show, a Halloween party sponsored by the local Kiss station, I ask Jeff Gordon what she said. He laughs and turns red but is too much of a gentleman to repeat it. When I ask Diplo the same thing later, he mumbles that it was “very sexual, kind of weird” before softening his stance and calling it “cute.”
The average age of this crowd is about 22, and even at 8:30 p.m. they're raring for a good time. I spot a Mister Rogers who appears to be on every drug in the neighborhood, a wasted Bob Ross with a prop paint palette, two Day of the Dead skeletons ecstatically grinding, and a gaggle of women whose group costume concept is “The Purge but sexy.”
Jeff Gordon and I park ourselves backstage. He hands me a pair of earplugs, and I need them: Diplo peels off his coat and saunters to the turntable, where he takes in the bedlam before pressing a button that kicks off a body-reverberating beat and then the sound of 7,000 people screaming all at once.
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Wild as his shows are, it's not the club where Diplo ascends to his truest form. I'd argue that would be on Instagram, where he compulsively broadcasts his whirlwind life for his 5.7 million followers. (He does not run his own Twitter anymore after such ill-advised tweets as “Someone should make a kickstarter to get taylor swift a booty.”) On Instagram, we see him DJ'ing at his Vegas residency and at the top of the Sydney Harbour Bridge. Meeting Elton John and meeting Dr. Phil. Hanging out with his children, Lockett, 9, and Lazer, 5. Hanging out with his chickens, names unknown.
Mostly we see shirtlessness. There's Diplo, shirtless on a mountain. Diplo, shirtless in an airplane bathroom. Diplo, shirtless in his Calvin Klein underwear ad. Diplo, shirtless, gazing into a body of water, possibly with an erection. (That one made headlines.) Diplo, shirtless in an unidentifiable location, his body adorned with a collection of tattoos that could fill an illegal aquarium run out of an aboveground pool in the Florida Keys—a crawfish, a shark, a manatee holding a machine gun, a turtle with a yin-yang shell smoking a blunt.
The updates are tempered with captions that are genuinely funny. “I was having a great time until I remembered that bees are dying at an alarming rate,” on a shot of him lounging on a boat next to an anonymous woman in a thong bikini. “I hope the fbi guy tracking my search history has learned as much about tractors this week as I have,” on a portrait in which he's wearing a Wynonna and Naomi Judd T-shirt and a cowboy hat. “If he didn't have such a razor-sharp wit,” DJ and producer Mark Ronson told me, “I don't think he'd get away with some of the handsome-boy posts that he does.”
Observing Diplo through this lens feels like watching someone do an extended bit about being a world-famous DJ. His life is as absurd as it is aspirational, and he leads with the absurdity. The result is a 41-year-old man with the self-deprecating tone of a millennial woman reared on 30 Rock and the meme literacy of a Gen Z'er. If everyone on social media is performing constantly, he lets you in on that fact. There is an authenticity to his inauthenticity. Another core tenet of the Diplo brand.
I first met Diplo in Los Angeles earlier that week, at a smoothie-bowl place next door to a private celebrity gym. I had no idea what was happening inside the private celebrity gym because its frosted-glass windows concealed the horrors within, but I knew the place meant business because the signage included a mysterious anvil logo. Diplo was there preparing for a Tough Mudder. The day of the race, he told Instagram he was “heading straight from the night club to a 14 mile obstacle course with zero training” with the hashtag #prayfordiplo.
“It sucks that it does matter so much, because if I didn't have all those peripheral things about me on social media, people wouldn't pay attention to my music,” he said, admitting that he spends way too much time on Instagram. “If people can identify with you as a human being, they're going to like you more for what you do.” This approach is working: If Diplo used to be an aggressively in-your-face acquired taste, now he's way more palatable to a wider audience, even—or maybe especially—when he's gleefully pushing the boundaries of good taste.
I was initially taken aback by how normal, and even slightly tired, he looked in jeans and a long-sleeve Vampire Weekend crewneck. (I would later see him walking around unnecessarily bare-chested and realize it was the shirt that was throwing me off.) He was not wearing underwear, which I know because about 30 minutes into our conversation he told me, “I don't even have underwear on. I couldn't find any when I went to the gym.”
As Diplo sipped his smoothie—spinach, banana, and almond butter plus two scoops of CBD powder—Patrick Schwarzenegger, son of Arnold, came over to our table to say hello. He and Diplo traded notes on recent workouts that sounded like they violate the Geneva Conventions. (Patrick: “You sit in this chair, and it's like an electric-magnetic-pulse thing that shocks through your body over and over.” Diplo: “I've done that, because I do the workout where you tie the whole thing to your body and do like 20 minutes of that.”)
“He doesn't think that he's good enough at anything. He has crazy low self-esteem. It's so interesting, because he's one of the most talented and attractive people in the world. But he doesn't know it.” —Sia
Turning 40 didn't clarify anything for Diplo, he says, except that he had to work out a lot harder to stay in shape, which is biologically true for everyone but an especially pressing concern for someone whose torso is exposed so frequently. Mainly, he was relieved. Relieved to no longer be “fake older,” a term he threw out as if it's a standard demographic category on the U.S. Census before clarifying that he meant the ages of 35 to 40. “I was kind of the dorky middle-aged guy, and I'm now just the cool older guy,” he explained. Getting older hasn't lessened his desire to stay on top of the new, music or otherwise. His current obsession is TikTok, a social media platform for posting short videos set to music that's most popular with children born after George W. Bush's first term. When an assistant mentioned that ISIS has reportedly been posting videos on TikTok, Diplo sarcastically deadpanned: “Are they good ones, or no? I'll follow them.”
Talking to Diplo can feel like hanging out with that one friend who is always on, who is always performing a little bit, who couldn't turn it off even if they tried. This performance, in some ways, functions to obscure Diplo's relentless ambition. “I for sure feel everything is a competition,” he told me. “You can always say like, Only compete with yourself, but no—fuck everybody else. In my mind, I'm trying to take down everybody. Not in a malicious way, but just in a way where I want to be the best at everything.”
Diplo's refusal to rest, his nonstop pursuit of the next thing and the next thing and the next thing after that, has obviously served him well. It's an itch he'll never be able to scratch—and maybe doesn't want to. “I think when you find contentment, maybe that's perfect harmony with the world. But I never do. I always feel like I could do more,” he says. “I'm not going to be content. Hopefully I never will be.”
The pop star Sia, who has known and worked with Diplo for more than a decade, most recently in the supergroup LSD, called him “the sweetest thing in the world” and “one of the most insecure boys I've ever met.” Not when he's making music, she explained—at that he's confident and decisive—but in terms of personal relationships and how to pose in photos and the like. “He doesn't think that he's good enough at anything. He has crazy low self-esteem,” she said. “It's so interesting, because he's one of the most talented and attractive people in the world. But he doesn't know it.”
“I think I found true love with my kids. I get lonely sometimes, I might have bouts of depression. But my kids, they love me. And they can't escape me.” —Diplo
11:30 p.m. A private jet, somewhere over South Carolina.
The sparkling water that the flight attendant dispenses is as crisp as an autumn morning in heaven's apple orchard. The aloe-infused socks that Joe, the personal photographer, hands me are as cozy as a space heater wrapped in a Patagonia fleece. The toilet seat, which is hidden inside what appears to be a padded leather armchair so that I am totally confused and slightly panicked when I first enter the bathroom, is both warmer and softer than any bed I've ever slept on. And Diplo, well… Diplo is furious.
After his Charlotte show, a mob of fans swarmed him for photos. He barks at his tour manager, Luke, and tour assistant, Eli, for letting it happen, and it feels like when you'd be at a friend's house for dinner and their dad would start yelling at them in front of you. The pair are brothers (Eli is younger by four years) who grew up in Idaho, and they possess an elusive mix of traits that make them perfect for the gig: the chill of Ultimate Frisbee players and the swift efficiency of the Secret Service.
Even though Eli bears the brunt of most of the criticism tonight (among his transgressions: momentarily forgetting to carry Diplo's bags, including a Dior tote embroidered with the word “DIPLO”), he shrugs it off. “It's a very good, brotherly type of relationship, where we'll be total bros and then just have a shitty day,” he tells me. “I probably spend more time with him than anyone else on tour.” Before this, Eli was a firefighter. When I ask him which job is more stressful, he says, “The firefighting, you know what you do in every situation. There are set guidelines. But this, it's all playing on mood.”
We've also been joined by a petite young woman, not older than 25, with platinum-bleached hair, an oversize 'NSync shirt, and pouty lips so mesmerizingly glossy I can see my reflection in them.
Diplo can have such a specific effect on women that the Kinsey Institute should award somebody a scientific grant to study it. It's not that he's good-looking, which is obvious. It's that he inspires a sort of revelatory shamelessness. You can't scroll through his Instagram comments for a millisecond without seeing someone calling him “daddy.” In 2013, a high school teacher was reportedly fired after tweeting at him a video of herself topless and twerking upside down. “Much of our relationship is just being spent trying not to have sex so that we wouldn't ruin our business relationship, because he's super-duper hot,” Sia even told me during our phone call. “This year I wrote him a text, and I said, ‘Hey, listen, you're like one of five people that I'm sexually attracted to, and now that I've decided to be single for the rest of my life and I just adopted a son, I don't have time for a relationship.… If you're interested in some no-strings sex, then hit me up.’ ”
Diplo follows over 6,500 people on Instagram, about 6,000 of whom are women blessed with figures that look like they were dreamed up by a 13-year-old boy in the margins of his spiral notebooks. I wonder if that's where he meets most women. The answer, according to Diplo, is both “no, just like in real life” and “yeah, I've been guilty of meeting girls on there.”
While we're suspended in the air thousands of miles above the earth, Diplo mauls a plate of Cajun chicken pasta (“I'm always trying to be a vegan; I'm about to do another diet tomorrow”) and ruminates on the lack of intimacy in modern sexual relationships. “Kids are very sexual, with these weird apps, and they lose the accountability of their emotions because they don't really connect with people. So sex becomes a little too mundane,” he says, suddenly sounding much older than his years. He takes a contemplative bite of garlic bread. “I've probably got the same problem. But I am very into the women I'm with, and sex, so it's not just sex with them.”
He doesn't “really believe” in marriage but feels as good as settled down with Lockett and Lazer. They live with their mother, his ex-girlfriend Kathryn Lockhart, but he sees them whenever he's in Los Angeles. “I think I found true love with my kids. I get lonely sometimes, I might have bouts of depression. But my kids, they love me. And they can't escape me,” he says. “Any girlfriend would end up breaking up with me because I'm so busy, and I'm just a bad boyfriend. My kids, they literally can't. My job is to be good to them.”
Briefly: While in Los Angeles, I accompanied him to his Beachwood Canyon house, where he stopped for 20 minutes before taking off again to attend a Morgan Wallen concert. He used his short interlude at home to cuddle both his sons, spin a basketball on his fingertip to impress Lockett, unpack a box of vegan ice cream (shirtless), put the dry ice from the ice cream delivery into bowls to entertain the boys (“There's Harry Potter magic happening in the sink!”), and tenderly spoon-feed Lazer chocolate ice cream from the carton (“You only get a little bit, baby boy”).
I ask Diplo if he always knew that he wanted to have children.
“Not really,” he says. “Then my ex-girlfriend got pregnant with somebody else and I was like, ‘Damn,’ because we had almost had a baby together.” He's referring to M.I.A., the British singer-rapper with whom he scored his first hit, 2007's “Paper Planes.” They dated for five years but, after breaking up in 2008, went on to have acrimonious back-and-forths in the press for longer than they had been together.
“She had a baby immediately, and I was like, ‘What the fuck?’ ” he recalls. “I kind of lost all hope in that relationship. And then I had a kid, probably like a year after that, because I was just like, ‘Fuck it, I want a kid.’ ”
3 a.m. Miami, Florida.
Inside a rooftop restaurant situated above a smoke-filled strip club, Diplo is dismantling a whole head of roasted cauliflower with the dexterity and precision of a professional chef. Walshy Fire, the affable Jamaican-American DJ who is part of Diplo's dancehall-inflected trio, Major Lazer, is digging into a communal salad that is the size of an entire Sweetgreen's worth of vegetables dumped into a bathtub. In this club, we care about reaching our recommended daily fiber intake.
We've just come from Diplo's second set of the night, a secret Major Lazer show at a venue called The Compound. This crowd was more intimate and the music all dancehall and reggaeton, in contrast to the more mainstream pop hits he was blasting over in Charlotte. Major Lazer's next album is due out this spring; it may be their last, though Diplo can see the group continuing as a collective without him. Plus, like everything he touches, Major Lazer doesn’t exist in purely one form: their animated series about an eponymous Jamaican superhero, which consists of trippy bite-sized episodes styled after ‘80s cartoons, is also returning for a second season later this year.
Diplo has been revived. He's in his element, and that element is Florida—a vibe he plays up with exaggerated dirtbagginess. Born in Mississippi, he grew up in the Daytona Beach area listening to everything from Miami bass to reggae to heavy metal. Mom worked as a supermarket clerk, while Dad, a Vietnam veteran who went to college when he was in his 30s, owned a bait shop. Diplo credits his father with giving him his sense of drive and determination. “I don't think he knows that, 'cause I was such a bad kid,” he says. “But I remembered everything he taught me.” By “bad kid,” he means fighting, shoplifting, cursing out teachers, and just generally “being a shithead” at school. “I had really bad friends,” he explains.
One of those friends is Sam Borkson, who cofounded the art collaborative FriendsWithYou and has joined us here. “We both would take turns getting thrown out of class,” he confirms conspiratorially. “And they would put us right back together! We'd just terrorize the fucking class.”
Diplo eventually made his way up to Temple University, in Philadelphia, where he studied film. He dropped out just shy of graduation and started working as an after-school teacher's aide, but he remained obsessed with music. Mark Ronson recalled meeting him around that time through a mutual friend, Ben, at the Silk City diner, an establishment whose name they'd eventually lift for their Grammy-award-winning collaboration. “Wes was maybe the biggest record nerd of all of us. He sat, sort of one-upping me of knowledge,” Ronson told me. “I just remember being vaguely annoyed about the whole evening and just being like, ‘Yo, Ben, your friend is a little too much.’ ”
Soon enough, Diplo channeled that energy into Hollertronix, a legendary weekly dance party he started in 2002 with his friend DJ Lowbudget. They ground out experimental mash-ups at a Ukrainian social club in Philly, early predecessors to his signature style of dipping into multiple genres simultaneously. Though Hollertronix remained mostly an underground sensation, one of their mixtapes landed on the New York Times' albums-of-the-year list in 2003. After “Paper Planes” went platinum, bigger and more mainstream names came calling, seeking out Diplo's skill for creating cutting-edge beats and his fingerprints to lend their projects a patina of cool. By 2014, he was able to credibly release an album titled Random White Dude Be Everywhere, and he's only been more everywhere since.
When Diplo started Major Lazer, in 2008, critics began to accuse him of cultural appropriation. He has fielded questions about the topic numerous times over, usually without tact. “I don't…really…fucking care,” he told The Guardian in 2018. “What kind of music am I supposed to make? Being a white American, you have zero cultural capital, unless you're doing Appalachian fiddle music or something.” He is more careful when I bring the subject up. “I'm not sure where I'm supposed to go,” he says. “Anybody has the freedom and right to do anything creatively, as long as their heart's in it.” Ironically enough, Diplo says, he's faced the most difficulty trying to expand into country music. “Country was hardest to break into, like people [were] not accepting me there,” he says. “I've only found a few artists that were like, ‘I'll take a chance with you.’ ”
After the cauliflower head is decimated into florets, a psychedelic Macho Man Randy Savage costume materializes and Diplo strips out of his tie-dyed Haile Selassie T-shirt and black jeans down to his emerald green boxer briefs.
“I'm definitely not getting laid tonight if I wear this,” he says, wriggling a leg into a multicolored jumpsuit. “But maybe it's time I don't get laid.”
“Maybe you get laid by your truest love,” Sam offers up helpfully.
We pile into an elevator to descend into the depths of E11EVEN, where a security guard escorts our conga line out to the DJ booth. You know that Hieronymus Bosch painting of hell? Imagine that, but with bottle service. The most precarious stripper pole known to man juts out of the middle of the floor, a wobbly steel spike waiting for the one true dancer who can conquer it. She finally appears and climbs to the top to execute a gravity-defying upside-down split, better at her job than anyone I've ever seen in my life.
The DJ booth is guarded more intensely than the White House, but one woman, dressed as Princess Jasmine, is granted entry. She bounces her hips swiftly and efficiently to deep house for a while before she remembers that she has a question for Diplo.
“Can I bring…,” she begins, turning her heart-shaped face up sweetly and batting her eyelashes. Diplo leans in to hear her.
“…my fiancé in here?” She flashes a boulder of an engagement ring.
“Who's your fiancé?” he asks her. Princess Jasmine points to the left of the DJ booth, where a man in an Aladdin vest waits, puppy-like, on the other side of the glass. He smiles and waves eagerly.
“That guy?” Diplo asks, and then, without waiting for an answer, “No.”
Jasmine skulks away. Soon we're joined by a brunette with a sky-high ponytail and a visible rhinestone thong whose Halloween costume is a Sexy Bratz doll. (So a Bratz doll.) I ask her how she knows Diplo. “I met him in Vegas. For my 21st birthday!” she explains. “I'm 23 now. I've known him for a while, actually.”
6:45 a.m.
Eli tells me he has some bad news: The night's not over. Diplo changes back into his civilian clothes; then we're shuttled across the street to Club Space, where we mostly stand there watching him scroll through his phone amid the pulsating music until he decides he's done. By the time we get back outside, it's well past 7 a.m. I thought I'd be delirious by now, but instead I have that adrenaline rush people get that lets them lift cars off children. Diplo's weekend will continue later today—with a festival performance in San Antonio, followed by a set at a club in Las Vegas. But for now, he needs to get some sleep.
“Diplo!” a woman in a skintight white halter yells out, her curls bouncing as she jumps up and down to get his attention. “You are! The muthafuckin' man!”
He strolls over and adjusts her top.
“Your boob's hanging out,” he says. Then, his work done for now, he fixes his cowboy hat and walks off into the Florida sunrise.
Gabriella Paiella is a GQ staff writer.
A version of this story originally appeared in the February 2020 issue with the title “Workin' 5 to 9.”
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PRODUCTION CREDITS:
Photographs by Charlotte Rutherford
Styled by Mobolaji Dawodu
Grooming by Johnny Hernandez using Dior Backstage Face and Body Foundation
Tailoring by Tatyana Sargsyan and Karina Malkhasyan
Set design by Brian Crumley for Rob Strauss Studio
Produced by JNProduction
Originally Appeared on GQ
