Why Macklemore Risked It All for 'White Privilege II'

To make his new album, the Seattle MC had to finally confront his demons – not to mention his place in hip-hop, and white America

Macklemore sends a text at a quarter to noon: "Pulling up in 1 min. I'm in a crimson Hummer."

The Hummer part's a joke, it turns out, but right on time, the Seattle hip-hop star arrives in something no less eye-popping: a black 2008 Cadillac DTS Biarritz with tinted windows, a cream-color vinyl top, whitewall tires and rows of tiny cactuses painted along its rear flanks. Macklemore – 32, Seattle-born and the hugest white rapper since Eminem – became a Cadillac obsessive as a kid, mainlining California gangsta rap through his Walkman; he bought the DTS a few years ago "with my first real rap money," he says. He's got an arm draped over the steering wheel and an 18-karat-gold, diamond-faced Rolex President on his wrist.

Puncturing the aura of ostentation is the molded plastic car seat mounted behind him: property of Macklemore's nine-month-old daughter, Sloane. Also puncturing it is the car's smashed grille: "I fucked it up yesterday," he says. "I was driving, on my phone, looking at World Star" – a video-sharing site devoted to hip-hop culture – "and I was thinking, 'This is a really stupid thing to be doing.' And right at that moment, I rear-ended a truck."

He grimaces, shaking his head, and we pull out. It's a January day in Seattle, and Macklemore, born Ben Haggerty, has bigger things to worry about. He's getting ready to put out This Unruly Mess I've Made, his sixth release and second album with creative partner and musical architect Ryan Lewis. Their debut LP was 2012's smash The Heist, which went platinum and controversially beat out Kendrick Lamar, Drake, Jay Z and Kanye West for the Best Rap Album Grammy. It featured, among other hits, the inescapable "Thrift Shop" – an ode to swagger rummaging through Goodwill bins that spent six weeks at Number One, and which has earned an astonishing 863 million views and counting on YouTube.

Unruly Mess' lead single, "Downtown" – a B-boy operetta of old-school rap and Freddie Mercury-indebted theatricalism – is well on its way to platinum certification, and Macklemore's promo duties for the album are kicking into gear: Tonight, he and Lewis will fly to Phoenix, where they're launching a 25-city tour. Before the flight, though, Macklemore has some errands to run, a last-minute rehearsal to pop in on, and most important – because he is an alcoholic and a drug addict – a recovery meeting to attend. When he gets there, he'll take a seat in a beat-up chair, fidget anxiously with the drawstring of his hoodie, and listen to the stories of men and women he's come to know intimately. He will thank them for sharing, then talk about how – even though he hasn't had a drop of alcohol in seven years – he has relapsed, several times, with several different drugs, since The Heist transformed him from an underground MC with regional buzz to a world-famous pop star. He'll talk about how he lied about these relapses to his wife, Tricia Davis, whom he married last year in his parents' yard, a month after Sloane was born. And he'll tell his fellow addicts that he's frightened: Leaving town, he's unsure how he'll be able to stay clean without this group. "If I don't prioritize my recovery, it's only so long till I'm miserable or I'm loaded," he'll tell me afterward. "The drug I take depends on the relapse. It could be a pill. Lean. Weed. Something I snort. Something I eat. It doesn't matter – if I put anything in my body, I want more."

But that meeting's not for a couple of hours, and right now Macklemore needs to buy an electric razor "and some deodorant too," so he points the Cadillac toward a downtown Target. Some stars would delegate such chores to lackeys, but Macklemore likes to feel he can still do mundane stuff in public. At the Target, he faces a bewildering array of Brauns and Norelcos, and a white, fortyish employee stocking shelves notices his indecision. "My husband has this one, and he loves it," she says. Macklemore settles on a high-end model with a $201.99 price tag and a feature called FlexMotion Tec, at which point she adds, "Could I possibly get a picture with you?" Macklemore assents. When he goes to pay, the cashier, a dreadlocked black guy with a name tag that reads Christopher, tells him, "You probably get this a lot, but you look exactly like Macklemore – I know you're not him, so I'm sorry, but I had to say it anyway."

"It's OK," replies Macklemore, seemingly thrown – after all, he has the most recognizable mug in town that doesn't belong to a Seahawk. "I do get that a lot."

Back in the Cadillac, several sidewalk fan-selfies later, Macklemore exhales: "That was intense. I think I took as many pictures just now as I have in the last year." He adds, "It's cool. I don't go to Target every day, but at the same time, I don't want to not be able to go to Target. And if I started tripping about people wanting to take photos with me" – he pauses, deciding how to word this – "then I would not be very spiritually on-point."

Spiritual on-pointness matters a lot to Macklemore, from his sobriety struggles to his music. Although he broke big with two party songs – "Thrift Shop" and the stomping "Can't Hold Us" – they both contained inspirational motifs about rejecting conformity and projecting self-confidence; a subsequent Heist hit, "Same Love," championed marriage equality. Since the very start of Macklemore's career – back when he was a high school backpack-rapper spitting preposterously principled verses and dense abstractions in a multiethnic crew called Elevated Elements – what has united his music is its smoldering earnestness and abiding sense of conscience.

That's as true on Unruly Mess as ever. On the opening track, Macklemore describes the entertainment industry as an insecurity-fueled, congratulations-hungry farce; on "Kevin," inspired by the prescription-drug overdose of a friend, he decries Big Pharma as a gang of murderous profiteers protected by a hypocritical justice system. Most ambitiously – and trickily – he devotes nine minutes to a song called "White Privilege II," which raises a swarm of questions about our racist society and Macklemore's own ongoing complicity, as a white rapper, within it. None of these tracks reflect what you'd call traditionally commercial impulses, and while Macklemore denies that the massive success of The Heist prompted a conscious swerve away from pop accessibility, the duo's manager, Zach Quillen, acknowledges that a song like "White Privilege II" might alienate "Thrift Shop" fans. "It might give some of our audience whiplash," he says. "On one hand, we had greater success with The Heist than we ever could have predicted, and so we have some capital to spend. On the other hand, it's insanely risky."

Driving southeast, Macklemore wants to grab a bite. "Do you like pho?" he asks. He parks outside a Vietnamese restaurant called Pho Bac, then pops into a nearby jewelry shop to say hello to the owner. "What's up, Lang?" Macklemore calls out. Lang, a stocky guy sitting behind glittering display cases, replies, "Hey! Mack!" and grins big as he rises for a handshake. Macklemore went to high school minutes from here, and it's important to him to feel as though he's still enmeshed in the fabric of city life, especially as it exists outside of affluent enclaves. The employees at Pho Bac greet him fondly, as does a fiftyish black woman who asks him to autograph two one-dollar bills and a 10 for her kids.

Our pho has barely arrived when Macklemore checks his watch and realizes the recovery meeting has started. "Damn, I keep showing up late," he says, pulling on his coat. Bowls unfinished, we settle the check and have just closed the Cadillac's doors when a middle-aged Hispanic guy knocks hard on the passenger-side window. "My daughter is actually a big fan," he says. "Can I take a picture?"

Macklemore asks me not to specify which recovery program he uses, adding, "I'm not bringing you because I want to 'show the writer.' I want to be transparent: This is just what I'm doing today." His relationship to drugs began in his teens and has never unfolded in moderation. "When I do drugs, the only thing I think about is how I'm going to get more drugs," he says. In adolescence, "high on weed or drunk off malt liquor," he'd act out in ways large and small: stealing cash from his job at Burger King, "smashing car windows to steal change to buy 40s, doing graffiti, riding in cars my friends stole. I've always been drawn to the grimy shit."

This wasn't remotely a function of economic need – Haggerty grew up well-off – but rather "a rite of passage, hormonal changes, trying to fit in, trying to be known, and liquor didn't help." In graffiti and hip-hop, though, he found artistic pursuits that, taken seriously, demanded not just daring but devotion. Nurturing this side of him, his parents sent Haggerty to a summer art course at Pratt Institute in Brooklyn, as a teenager. It didn't go well: "I wasted an entire summer getting drunk and high and not making art, and I had to make up a lie to my parents, that the air conditioner leaked on my artwork and I had to throw it away." It was at Pratt that he came up with the name Macklemore – a lark that stuck – and where he met a kid who told him, "'Bro, you're an alcoholic.' And I had never thought of that before. I knew that things happened when I did drugs and when I drank, but never applied that word to me."

When Rolling Stone first profiled Macklemore, in 2013, he took us to a recovery meeting in Austin, where he and Lewis were playing South by Southwest. "I didn't say this then, but I'd relapsed right before that interview, and Tricia was like, 'You need to get to a meeting now,' " he says. His troubles continued as he got increasingly famous, with stints of sobriety interrupted by backslides. He drank "lean" – prescription codeine cough syrup – and can speak authoritatively about its deeply unglamorous side effects. ("It makes you constipated. So when you stop drinking lean, you get fucking backed up with copious amounts of poop, but you can't poop, so then, at a certain point, that has to come out. And when it does, it's usually in the form of diarrhea.") But the real effects of his addictions were more insidious. Depressed and isolated as he snuck around seeking his next score, Macklemore hid his drug use from those closest to him: "I'm trying to maintain like everything's all good, but in actuality, from the moment that I wake up to the moment that I go to bed, I just care about getting drugs." There have been injuries, too. "One of his rock bottoms would probably be passing out in the bathroom and smashing his face into a sink," Lewis tells me. "That's happened numerous times," Macklemore admits, adding, "I've put myself behind the wheel with so many drugs in my system … I don't say this to be dramatic, but I should've been dead a long time ago."

Macklemore's meeting is in a small hall with scuffed furniture and weathered carpeting, in a decreasingly black neighborhood. "These streets were my playground," he says. "I spent more time out here than in class. It's really sad: Amazon" – Seattle's most prominent new-money employer – "has jacked up the rents so fucking high." When he laments gentrification, it's from the necessarily conflicted perspective of a guy who recently bought a $2.1 million house in the tony Capitol Hill area, but it feels genuine. In the meeting, he is one of four white people among 26 attendees, and one of a handful who looks younger than 40. Macklemore waves, gives out hugs. A man starts talking about his rough childhood, and Macklemore ducks into the hall and returns with a coffeepot; he walks the room, pouring everybody cups. Next up is a big guy who starts crying as he apologizes to another addict for yelling at her the other day.

At the past few meetings Macklemore's attended, he hasn't shared, but today he is compelled to talk next. He tells a story about his difficulty making amends with Tricia. "I knocked some [amends] out, but I still had my wife, and I didn't know where to start," he says. "How many years do I go back? What do I do? Eventually, I relapsed. So I was high, and I was in bed with her, and I was about to get more drugs, and I tried to make my amends there, as I was high, to try to prevent myself from getting more drugs." His gaze drops to the floor. "I'm about to go on the road tonight. I've been in this place of just, like, my business and my career and what I need, and it's that self-will that leads me to sickness. I'm not living the program. I've been sitting here listening, showing up late, leaving early, trying to get something out of this, but I'm not. I have to do the work. I need to think about other people, because if I only think about myself, I will get loaded again."

"Call us," someone says. "Call us," other voices affirm.

A guy in sandals pipes up, says he's sent Macklemore texts in the past and that he hasn't written him back – but it's all good, he's still got love for him. Macklemore purses his lips and nods.

I'd rather not list sobriety times," says Macklemore when I ask him, afterward, how long he's been clean. "What's important is to say, 'I'm fucked up, I've been fucked up, I've lied.' I've been living a program of recovery for a year and a half, and 99 percent of the time it's been going great." He adds, "I'll be sitting in that hall, feeling fucking miserable with a Rolex on my wrist, a Cadillac in the parking lot and a house on Capitol Hill. And I look around the room and see people more spiritually connected and fulfilled than I am, and have far more serenity and peace in their life."

He draws a line from what just happened at the meeting to his own artistic goals: "Watching a man cry in front of a room of people, apologize and leave with more power and respect, in a true way? I strive for that when I make music. Write draft one, then tear it up and go deeper. Dig. When someone's truthful, it sets the room on fire. So for me, whether I'm sharing or writing a song, my question is, 'What am I hiding?' That's exactly what I need to say."

The next stop is a rehearsal space in the city's Industrial District. Lewis is there, wearing skinny jeans and chunky eyeglasses. His audacious, genre-jumbling productions and handiness with a big melody are Macklemore's semi-secret weapon. At the moment, Lewis is leading a small band through the duo's 2010 recovery narrative "Otherside." "For shits, can we scrap that horn line and try to come up with something more staccato?" Macklemore asks. Assenting, Lewis bleats out a new cadence with his mouth, and Owuor Arunga – the duo's trumpeter and Macklemore's old high school friend – replicates it expertly.

The idea for this tour is to start small – playing theaters with about seven buses and a 50-person crew, "spending about $70,000 to $80,000 a show and coming out a little bit ahead," according to Quillen – before doubling in scale for a European arena tour. They want the theater shows to feel special, and so no song is safe from change.

Work on This Unruly Mess I've Made began in 2014 and progressed slowly, both because of Macklemore's personal troubles and the duo's ambitions. Lewis, flush with Heist cash, splurged on sounds: For the opening alone – a song called "Light Tunnels" – he hired the Seahawks' drum line, a choir, a "12-to-15-piece string section," a harpist and a dulcimer player. The song took more than a year to finish. Macklemore, meanwhile, tried to overcome writer's block with stream-of-consciousness exercises he'd perform on a typewriter – an idea inspired by a book called The Artist's Way: "It was imperative for me to just get the cobwebs out." The duo drew from their Heist earnings to build their own recording spaces, and so the album, despite the elaborateness of its making, "cost less than a comparable sophomore album would have at a major label," Quillen says. "They spent less than $500,000."

On Macklemore's first solo album, titled Open Your Eyes and self-recorded when he was about 17, he balanced psilocybin-fueled spiritual searching with a nascent political radicalism. On a wondrously bizarre song called "Journey," he raps about doing magic mushrooms in the Olympic mountains and beatboxing to the sound of chirping birds, absorbing "their wisdom"; toward the track's end, he recounts a more pointed fantasy in which "I metamorphosize as a Native American, hijack the Santa Maria and assassinate Columbus." When I mention this song, Macklemore's face turns red, and he reminds me that it was made a long time ago. But he doesn't disavow the track either. "I was a high school kid, fired up on reading Howard Zinn for the first time," he says.

That radicalism extended to an aggressively atheist Macklemore calling religion a bigger killer than "suicide, AIDS and cancer combined," and, on another song, speculating that George W. Bush was behind the 9/11 attacks. By the 2012 release of The Heist, however, those rough edges were softened: Radicalism gave way to inspirationalism, and the influence of Howard Zinn gave way, in the album-opening "Ten Thousand Hours," to that of Malcolm Gladwell. Macklemore was and remains a proud independent artist who built a local following, slowly but surely, into a national one; when he linked up with Lewis his sound grew distinctly bigger and more melodic, and for The Heist they signed a distribution deal with an arm of Warner Music, allowing them to borrow some major-label muscle while remaining indie otherwise.

On Unruly Mess, Macklemore's confrontational side returns, and no song is more confrontational than "White Privilege II" – a sequel to a 2005 rumination on the same theme. The spark for the song came in late 2014, when Macklemore, appalled by the non-indictment of Darren Wilson in the death of Michael Brown, was photographed participating in a Black Lives Matter protest in Seattle. A hip-hop elder statesman (whose name Macklemore wants off the record) saw these pictures, sent Macklemore a direct message on Twitter, then gave him a call. "He was very complimentary about our music, then he led into, 'You have a platform, but silence is an action, and right now, you're being silent. You have an insight into these issues that you need to be speaking about, and, as a white rapper, it's important that you engage your audience' " – meaning white people.

The song went through an extensive process of revision: Macklemore looped in a number of activists, musicians, intellectuals and academics, and rewrote it based on their feedback. "As a white person stepping into any sort of anti-systemic-racism type of work, you need to consistently ask yourself, 'What is my intention?' Check yourself, check yourself, check yourself," he says. "There's no perfect version of this song," Lewis says.

Macklemore's conscience has a history of landing him, counterintuitively, in trouble. In 2014, after The Heist's Grammy win, he caught flak for sending a private message of apology to Kendrick Lamar, then posting a screenshot to Instagram, which many people thought was a self-serving act of contrition. Some LGBT critics deemed "Same Love" patronizing; others thought it wasn't Macklemore's place to criticize hip-hop, in the song's second verse, as broadly homophobic.

The valence of Macklemore's lyrics can vary depending on who feels addressed by them: Gay people don't need his permission to love one another, of course, but some reflexively homophobic listener of "Same Love" might find his prejudices challenged. Of the critiques that will emerge in response to "White Privilege II," Macklemore says, "This song was a processing-out-loud. It wasn't like, 'How can we beat critics to the punch? How can we exempt ourselves from this angle, this angle, this angle?' It was like, 'I can continue to be safe and to rest in my privilege, and to not speak up, and the system perpetuates itself, or I can try to engage in the conversation, knowing that I don't have all the answers, knowing that I have so much to learn.'"

When I mention mainstream whites who might be put off by the "Thrift Shop" guy rapping that the American flag is a symbol of white supremacy, Macklemore replies, "At a certain point, this song might affect sales or affect touring, but it just doesn't matter if I'm not speaking up – if I'm not pushing myself to speak the truth."

After rehearsal, Lewis rides his fat-tired black motorcycle, a modified Harley known as an Iron Guerilla, to the waterfront building he and Macklemore converted into their Seattle headquarters. On the ground floor is a recording room with a ton of audio gear, a wall of guitars and racks of outlandish garments spouting sequins, fringe and feathers. "Those are Ben's," Lewis notes. There is a kitschy velvet painting of a bald eagle, an oil painting of Drake dancing and a transfixing rendition of a naked Justin Bieber with maple syrup pouring down his chest onto a pancake balanced on his boner. "Ben spent a lot of time buying weird stuff on Etsy," Lewis says.

Macklemore arrives. Tricia, funny and warm, is upstairs, helping to tend to business, and Sloane is here too; he won't see her for a couple of weeks. She's a big kid for her age, with blue eyes and a little pair of winged Jeremy Scott Adidas on her feet. She extends her little fist toward me for a bump. "She's giving you dap!" Macklemore says, beaming with rap-dad delight.

A few hours later, he and Lewis board their Alaska Airlines flight to Phoenix. They fly coach, per usual; their destination is a Holiday Inn Express. The duo splash out in some ways – gold watches, cars, motorcycles, multimillion-dollar houses – but are spendthrift in others. "Tricia books our travel, and she's so cost-conscious," Quillen says. "That extends from flying coach to the hotels she gets us. We'll be like, 'Really? The Ramada Inn?' "

Rehearsal starts the following morning. The Macklemore crew has taken over the 5,000-seat Comerica Theatre a few days ahead of the tour's start to slap everything into shape. After eight hours of rapping the same songs over and over, Macklemore, feeling loopy, takes to spouting streams of gibberish. When the rehearsals end, he calls a meeting, asking everyone in the crew to sit in a big circle onstage. Crouched on a monitor, he says he's excited to work with everyone, that they're gonna have "a season like the Seahawks." Then he cedes the floor to the tour's security director, Terrell, who lays out ground rules, among them no use of social media behind the scenes and, also crucial, "no taking shits on the bus."

Everyone laughs, but Macklemore is clearly preoccupied. Soon enough he leaves the stage, changes into a hoodie and climbs into a car idling outside the theater – he's found a recovery meeting happening nearby, and he doesn't want to be late.