In ninth grade, Macklemore moved on to Garfield High School, alma mater of Jimi Hendrix and Quincy Jones. "It was this massive school, with no supervision, and I was like, 'Oh, I can skip class,'" he recalls. His initial attempts at rapping ("It started out with me beatboxing and being pretty horrible") were swiftly followed by his early experiences getting wasted. "The first time I drank, I did 12 shots of vodka by myself after school," he says. "I was like, 'Oh, this is nice,' and I just kept going – with a wife-beater on, listening to 'Thug Passion,' thinking I was the white Tupac." Soon he was a certified stoner, too. "As a freshman, I dated a superpopular girl who was a junior, and she smoked a bunch of weed," he says. "I was high every day, all the time. That's where my lunch money went. There was just no off switch."
After a few years of ups and downs – including a period when he avoided alcohol and marijuana in favor of lots of magic mushrooms – he enrolled at the Evergreen State College, a grades-free school in Olympia, Washington. In 2005, he self-released an album, The Language of My World, whose savvy blend of blue-state politics and self-deprecating humor made him a star on the Seattle club scene. "High school kids were really into him," says Seattle radio DJ Michele Myers, who started playing "Contradiction," a song about hip-hop sexism, on her KEXP-FM show. "He seemed to be everywhere."
As Macklemore's shows got bigger, his partying got more extreme. "I started to get more fucked up than ever," he says. "All of a sudden, you're young, you have this newfound attention – I was hooking up with random females, and the drugs started getting stronger. I always said that I would never do coke, and I broke that. I started doing a little bit of OxyContin, which scared the shit out of me."
Friends began to worry. "You assume when somebody's not replying to all your texts and calls that they're just too cool," says Lewis, who got to know Macklemore during the rapper's dark years. "But most of the time, I think he was alone, smoking in his bedroom."
By the summer of 2008, the steady stream of shows had dried up entirely, and Macklemore was regularly sipping lean – the codeine-laced drink popularized by Southern rappers like Lil Wayne – on top of everything else. At his father's urging, he entered a 35-day rehab program in Canada. "I hadn't put out music in a long time," he says. "I was pretty much broke."
He's stayed strictly sober since then, except for a brief backslide in 2011. "I fucked up a couple times – literally, two times – and sipped some lean," he says. "But I started working with a sponsor and got a lot healthier. It's been four and a half years since I've drunk alcohol, four and a half years since I've smoked weed, four and a half years since I've done cocaine."
Sober or not, Macklemore wouldn't be where he is today without Lewis, a majorly ambitious kid who started his first company at age 16. At times, the producer's Tom Haverford-level confidence seems to be the primary force behind their recent success; he's been known to call himself "Ryan Lewis Gosling," and he does bear a passing resemblance to the Hollywood heartthrob, if you squint just right. It was Lewis' idea to form Macklemore LLC, the self-run label that they've used to release all their music since 2010. "He fought me for a long time on that," says Lewis with a satisfied smirk. "When you've never started a business, all that shit's scary. In reality, you can make an LLC in, like, a day."
The duo's DIY ethic extends to their music videos, T-shirts and posters, all produced in-house. They're proud of their decision not to sign with a major label, or even an established indie. "We met with all those fools – it just was not for us," says Zach Quillen, their manager. They did, however, strike a pair of one-off deals with bigger corporations: The Warner Music Group-owned Alternative Distribution Alliance put their album, The Heist, in stores and on iTunes, and, unusually, the Warner Bros. radio department got "Thrift Shop" into heavy rotation on Top 40 stations across the country after the video took off on YouTube. "It's been one of the most requested songs since we got it," says Myers, the KEXP DJ. "It's what we call a breadwinner – a really high-energy song that gets everybody going."
Macklemore spends a lot of time thinking about another factor that he says has contributed to his sudden success – namely, his race. "I look at myself, like, how do I play into this?" he says. "Why is it that our concerts are made up of primarily white kids? And now that I have that demographic on lock, word. Let's talk about real shit, too. This is America, the land of institutionalized racism and appropriation."
It's a lot to process, and he has less time than ever for reflection. "I guess that's a good thing," he says. "I spent a lot of my life rapping and not making enough money to live, and gratefully, that's not the case anymore. But not having a foreseeable end date in sight is a little bit scary."
Life on the road can be challenging for a recovering addict – especially when the van rolls through a place like Austin, where the confluence of St. Patrick's Day weekend and SXSW means free booze is basically everywhere. Lewis says he and the rest of the gang don't make any special effort not to party around Macklemore. "He wants people to be able to be themselves, and I love Jameson," says Lewis. "And that's just not particularly how his addictions work. He's sneaky. If he's going to fuck up, it's going to be in the sneakiest way possible."
The day after the Woodies, Macklemore tells me that fame itself poses the greatest risk to his sobriety – that, in fact, he's been fighting back addictive urges even as "Thrift Shop" climbed the charts to Number One. "When you get people coming up to you and their reaction to seeing you in person is crying and uncontrollably shaking, it's a little weird," he says, late-afternoon light streaming across his face as he tries to savor a rare moment of stillness near his hotel pool. "At times it's overwhelming."
As if on cue, a cute brunette in cutoffs walks by and does a double take. "Are you Macklemore? Are you really? That's so cool!" He obliges her with a quick photo, then returns to our conversation. "The last three months haven't been good for me – the pressure, the expectation, the lack of sleep, the stress, the traveling," he admits. "I can't escape Macklemore. I just want to get the fuck out of my own head. And there's one way to do that that's very instantaneous, which is to get fucked up."
I ask how he's coping, and he thinks for a long time before answering. "I've . . . walked the line," he says slowly. "Drugs and alcohol will always be an issue for me. That's never going to change." He stares at the sky, choosing his words.
"I can say that right now, I'm sober," he says after a while. "I plan on remaining sober for the rest of the day. And starting over again tomorrow."
This story is from the April 11th, 2013 issue of Rolling Stone.
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