It's a little after 2:30 p.m. on a bright Sunday afternoon in New Jersey when I first watch Wiz Khalifa attempt to land an ollie. The 26-year-old Pittsburgh-born rapper is standing on a wide street that winds behind the PNC Banks Arts Center, an amphitheater off the Garden State Parkway about an hour southwest of New York City. He is here along with a half-dozen other artists and their crews on an August stop of his Under the Influence of Music Tour, and everyone has, oh, six or seven hours to burn. A handful of young photographers and band members, sweaty and shirtless, are running up an embankment or doing push-ups under the eye of a trainer. Ty Dolla $ign, an R&B singer who Wiz has helped elevate to prominence, is speeding up and down the street on a minibike. There is a small, mischievous smile on his face, as if he's imagining a version of Mario Kart where the characters smoke blunts while they drive.
Wiz, though, is focusing on only one thing: landing the ollie over a propped-up board that has pot leaves painted on its underside. For a half hour he goes back and forth, hoping to clear the eight-inch jump by kicking his back heel and sliding his front foot forward to level off. But on every single attempt, he clips the lip of the board and nearly wipes out, his branchy limbs and blond-tipped dreads splaying in different directions, his board flying off somewhere to be tracked down by whoever happens to be standing around.
Over the course of day I spend in his orbit, Wiz ollies hundreds of times. He ollies throughout the afternoon on the street while the tour's other artists relax in their massive, tinted busses. When the show starts around 6 p.m. he changes into a white basketball jersey and white basketball shorts and moves backstage to ollie for hours in a small space amongst stacks of suitcases. Women with perfectly done-up hair and clattering heels mill about, but Wiz's head mostly stays down, his eyes fixated on his feet. The clack of his board hitting the floor provides the afternoon with a sort of rhythm. From behind his DJ booth, DJ Drama yells at the crowd as he introduces one of the openers, Rich Homie Quan. Clack. Ty Dolla $ign sings his radio hit "Or Nah," which features a minute-long opening verse from Wiz himself. But he never once looks up. Clack.
Wiz isn't antisocial, exactly. He takes breaks to joke with his friends and solicit tips from dudes on the tour who can ollie and kickflip with ease. His grin has a quick trigger and he'll engage anyone who happens to be around. At one point he gets into a wrestling match with the more muscular tourmate Sage the Gemini, who all but pins him. Wiz is the most famous person on the overstuffed bill, but also the most visible even long after his obligations with me have been satisfied. By skateboarding he's mostly having fun and passing the time, but it also clearly gnaws at him that he can't master this skill. At one point in the day Wiz smacks into the turned-up board once again. "I hate not being able to do shit," he spits with exasperation. Then he skates over to a railing to go over his ollies while holding his balance.
Later when I sit down and talk to him, he tells me that he's been learning to skate for about four years.
"I had taught myself for a long time," he says. "But now I got one of my friends who's a professional skater who's really given me some pro tips" — he elongates the "o" in "pro" and the "i" in tips in the perfect drawl of a California surfer — "and it's helping me out. I'm diggin' it."
I ask him about his trouble landing the ollie, but before I can even finish the question he cuts me off.
"I'm gonna do that trick," he notes with forceful confidence. "It's just I haven't done it yet. I've done it but it was on different gravel, different skateboard. It was just totally different circumstances. It's like anything else. There's calculations and there's math to it and as soon as you put in the right equation you get it right. But it takes practice and practice and practice."
We're sitting in his dressing room, which is near the stage and separate from the danker, windowless spots every other artist and their crews have underground in the bowels of the amphitheater. Wiz's room, though, is the darkest. He has blacked it out using tie-dye curtains with hallucinogenic designs that look like they were pulled from an old Deadhead's living room. Aside from some sunlight peaking around the edges, the only thing illuminating the space are a few low blacklights that give the entire room a soft, purple glow. As we talk he rolls a joint the size of two of my index fingers from a pile of pre-ground weed and exhales right into my face. By the time I leave my head is swimming and the room has the haze of a dream. It's what every high school junior hopes living in a dorm is like.
Wiz has been putting on a version of the Under the Influence of Music Tour for the last three summers. Over that time he has become one of rap's most bankable stars, and last year he had a son, Sebastian, with his now-wife Amber Rose. His fifth studio album, Blacc Hollywood, is out this month, and I want to ask him about trying to remain a popular rapper in 2014.
Unlike 10 or 15 years ago when artists like 50 Cent, Outkast, and Missy Elliott thrived, pop music and rap music are now often separate concerns, with only a few rarified MCs like Drake and Lil Wayne able to bridge the gap between the two increasingly disparate audiences. Most rappers either have to choose to satisfy their core fans while putting a ceiling on their careers, or go full-on pop with no looking back, like Pitbull and Flo Rida. Even Nicki Minaj, both one of the most popular and most skilled rappers in the world, has had her career defined by the opposite pulls of what we now consider "rap" and "pop."
Wiz probably falls into the same category as Nicki Minaj, at once making peace offerings to the fans that popularized him (in his case with between-album mixtapes) while still maintaining a clear desire to grow his audience with crossover singles. After "divorcing" with Warner Bros. in 2009, Wiz quickly cultivated a large fanbase by making music that vigorously advocated for smoking as much pot as possible. Rappers have always rhymed about weed, obviously, but few have ever made it as central to their music as Wiz, who put out mixtapes with titles like "Burn After Rolling" and "Kush & Orange Juice" and rapped over airy, soothing beats that mimicked the pleasurable numbness of being high. It may seem odd to think of Wiz Khalifa as one of a generation's most influential rappers, but many of the art form's recent mutations — guys rapping more about doing drugs than selling them, beats bending toward smooth, icy atmospherics — were pioneered in large part on his mixtapes.
It was that groundwork that helped him blow up in 2010 with the No. 1 single "Black and Yellow," which itself charted a course for the second phase of his career. Though Wiz molded an identifiable sound for himself, his commercial singles have often been produced by people like Dr. Luke, Stargate, and Benny Blanco, who are most famous for writing timeless smashes for pop singers like Katy Perry and Miley Cyrus. But his most recent hit, "We Dem Boyz," retreats from that pop-driven sound in favor of the testosterone-fueled, Autotune-soaked street-rap of Chicago "drill" rappers like Chief Keef and Lil Durk. He acknowledges that the wedge between the rap and pop worlds was what drove him toward a grittier single.
"I wanted to take a different approach with this album. To come off with a more urban single was really my approach because there's a lot of urban DJs who love my music and love me, I just don't give 'em no mainstream records to play," he explains. "And that's really just as far as radio and labels go, because I don't know if you know, but the label says, 'Hey, this is what you gotta play from my artist.' And if I'm pushing a [pop song like] 'Roll Up' or something like that, then those hood DJs that really fuck with me don't get a chance to go in on those hood records like they want to."
I ask him how consciously he feels pop and rap tugging at him separately, but he answers me in the vague, slippery language of someone who has done enough interviews to know how to say something without saying anything.
"It's something that I juggled with before, but now it's something I'm pretty clear about how to handle it," he says. "That just had to do with getting things in line in my corner so there wasn't as much confusion, because at the end of the day everybody needs that. It's just when and how we supply them and it's calculated. Yeah. Nobody gets left out, though."
As our conversation grows longer and his joint much smaller — to be in the presence of Wiz Khalifa is to find yourself boggling at how stoned he must be at any given moment — his answers get a bit loopier, and his interest in my questions begins to dissipate. I ask him if he's ever considered getting into the politics of marijuana legalization and he doesn't even have to think about his answer.
"Nah. Hell nah. Politicians get shot." He pauses for a second. "Rappers get shot," he says, and I point out that, on balance, rappers probably get shot more than politicians. "Not weed rappers, though," he retorts. "I feel like I speak out enough for it in my music and how I conduct myself."
This is clear enough during his set. He descends from a platform puffing a blunt and will smoke two more during the hour or so he's performing. His eyes are low and droopy but, behind Kurt Cobain white sunglasses, in an extremely cool way. Wiz's writing can be plain and overly narrow, and on his 2012 album ONIFC, he often sounded bored on his own songs. But on stage he's a genuine rock star, moving around in a way that is innately enviable.
To the mostly white, teenage, male crowd in New Jersey, though, I don't think that's exactly his appeal. Instead, Wiz is something like a new sort of inspirational figure, using rap to get across the same sort of open-your-minds hippie-isms that started a revolution 50 years ago. When he was telling me about "mind frames" and "weed knowledge" earlier in the day, his words trailing off in between puffs of smoke, he sounded soupy. But in front of his audience — the majority of which are well below drinking age and wearing calf-high socks with weed leaves printed on them, some of whom were openly passed out by the time Wiz hit the stage — he was direct and clear about his worldview.
On the cab ride back to New York City, I opened my phone and scrolled through the notes I took on my phone of his between-song statements:
"We wanna see you do any and everything you can do."
"We gon' free our motherfucking minds."
"I want you to embrace your unique selves."
"You got the truth inside you, you don't gotta look for that shit."
"The universe couldn't be happier, and it pays us back every day."