Iggy Azalea Outtake for Billboard Magazine (2016)
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Four years ago, the Australian rapper became one of the biggest new stars in music. Now, she recounts her fall from pop’s heights, and the lessons she’s learned ahead of a comeback bid.
Iggy Azalea is worried that she’s about to get booed.

In a few hours, Azalea will head to Brooklyn for Demi Lovato’s performance at the Barclays Center on this freezing Friday in New York City. “I’m gonna come out and Demi’s gonna sing ‘Savior’ with me,” says Iggy, in between bites of a cheeseburger, as she sits at a boardroom table in a suite at the Mercer Hotel. She’ll ascend from beneath the stage as a surprise guest midway through the show to perform her new single, and Lovato will sing the vulnerable hook (“I’ve been looking for a savior/I’ve been looking for a hero in my corner”) as Azalea delivers verses about losing hope and trying to escape purgatory.

I tell Azalea that the arena crowd will go nuts when they see her. She isn’t so sure. “I hope so?” Azalea says, leaving a twinge on the final word. “You never really know.” She’s wearing a cropped black jacket over a printed tee and pink suede pants, and runs her right hand through her long, straight, taffy-colored hair. Her ring finger reads ‘Digital’ and her middle finger reads ‘Distortion,’ a tattoo dedicated to a planned sophomore album, Digital Distortion, that was never released.

Azalea, 27, explains that, a week earlier, she made a similar appearance in Australia, during Tyga’s set at a hip-hop festival in Melbourne. It was her first performance in her native country since 2013, when, poised to blow up in America, she opened for Beyonce on the Australian leg of the Mrs. Carter Show. Azalea’s stomach churned offstage as Tyga hyped up his mystery guest. “He says [to the crowd], ‘Okay, y’all know I couldn’t come out here without bringing out the queen of Australia,’” she recalls, her eyes widening. “I was like, ‘Oh, I don’t know. That’s a big statement. Are they gonna be like, “Boo, fuck you, bitch!”?’

Tyga’s crowd didn’t heckle Azalea when she arrived onstage; neither did Lovato’s a week later. At the Barclays Center, the rapper was met with a muted response as she slowly rose into view, but the cheers started to swell as she dug into the rapid-fire delivery of the second verse of “Savior.” Her presence at an arena show, the way she prowls the stage in stilettos and goads the fans into singing along with a chorus, is natural. She’s done this before, albeit not for a long time, and under much different circumstances. As she starts her comeback bid in earnest, the fear now lurking in her mind has nothing to do with her performance capabilities and everything to do with general perception — how the world receives and reacts to Iggy Azalea on a fundamental level in 2018.

Before it was like, ‘We’re at the top of the mountain, and we have to stay at the top,’” she says. “I slid down the mountain a bit.

She was supposed to headline Barclays Center two-and-a-half years ago. In December 2014, as she wrapped up a year of incredible mainstream success, Azalea announced an arena tour that would support an upcoming second album and include a stop in Brooklyn on October 11, 2015. At the time of the announcement, Azalea was a four-time Grammy nominee, and about to compete for best new artist. She had strung together a commercial run that most artists would kill for, following a few years as a minor hip-hop curiosity: her Def Jam Records debut, The New Classic, produced three Top 40 hits, including “Fancy” (featuring Charli XCX), which was crowned the 2014 song of the summer after spending seven weeks atop the Billboard Hot 100. With her guest spot on Ariana Grande’s concurrent smash single “Problem,” Azalea achieved a chart feat that literally only the Beatles had previously accomplished. She became a true crossover success, performing at Lollapalooza, Summer Jam and the iHeartRadio Music Festival, as she transformed into that most dubious of figures: the chart-topping white rapper.

For as inescapable as Azalea’s music was during her year-long run, her social media dust-ups and defensive responses to accusations of cultural appropriation that came from within and around the hip-hop community became just as ubiquitous. A mass-marketed rap artist who invited questions of representation and authenticity as soon as “First thing’s first, I’m the realest” rolled off her tongue, Azalea made headlines for shrugging off hip-hop legends and feuding with the press more often than she did for setting chart records. When asked about the backlash in a pre-Grammys interview with GQ in 2015, she answered by pointing to her accolades: “Uh, awards season helps. Anytime where people get to choose who they want to have a voice and they choose me, I just think that makes it worth it.” She ended up leaving the Grammys empty-handed — and got into a Twitter feud with Papa John’s Pizza during the ceremony.

The battles took a toll on her psyche. Azalea’s 2015 arena tour, dubbed The Great Escape, never happened — its 21 announced shows were all cancelled in May 2015. She chalked up the move to a “creative change of heart” in a statement to fans, confirming that her second album was not near completion. She also admitted that she required some downtime after a nonstop year. “I was mentally exhausted,” she says now, “and I wasn’t really in a place to start making new music, honestly. … I never really was recording my second album in the height of my success, weirdly enough.” Azalea released two singles in 2015, the Jennifer Hudson collaboration “Trouble” and the much-ballyhooed Britney Spears team-up “Pretty Girls,” and both underperformed relative to her 2014 run. Her follow-up to The New Classic, long carrying the title Digital Distortion, has yet to be released. Her skyrocketing career had quickly fallen back to earth.

Azalea looks back on her year in the spotlight “in the way anybody looks back on life: there are moments that I loved, and there are moments where I cringe. I think it’s as simple as an outfit you wore at a party… or like when you’re grown up and you look back at your college days. You look back at it with love, and there are other things you were like, ‘Oh God, I was such an idiot.’

In person, Azalea is charming and enthusiastic; she makes her voice cartoonishly louder when she wants to land a punchline, and raves about the Mercer Hotel’s Thai coconut chicken soup for a solid two minutes after lapping up a bowl alongside her cheeseburger. She’s also candid about her struggles over the past three years, the mental health “retreat” she took in 2017 that refreshed her attitude, as well as where she’s at today, as she attempts to restart with a new label and management team. “I’m not on top anymore, honey,” she admits with a knowing shrug. “I’m still here, cleaning up the mess now. At least now, though, I have some perspective on it. And I will say that’s good, because it’s hard to resolve things with anything when you’re still in the thick of it.

I ask if she has any regrets about that whirlwind period of her life, when she became one of the biggest music stars on the planet. “I have regrets, yes, tons, of course,” Azalea says. “Anybody’s gonna… so many regrets.” Her eyes begin to water. “But… I don’t beat myself up about it at the same time, because it, everything, was like landing on Mars.” She exhales. “I just think it’s a lot for anybody to digest.

Azalea wasn’t an unknown entity prior to “Fancy”: the Mullumbimby, New South Wales native released her debut mixtape, Ignorant Art, in 2011, and, under the mentorship of her Hustle Gang boss T.I., made the XXL ‘Freshman List’ the following year. Prior singles like “Work” and “Bounce” didn’t become Top 40 fodder, but her collaboration with Charli XCX was an obvious anthem for pop radio when it was released in February 2014. The elasticity of the synths, Charli’s shambolic hook, the Clueless-inspired music video and even Azalea’s lyrical branding (“Who dat, who dat? I-G-G-Y”) were ripe for mass consumption. Nothing works as a mainstream entry point to a newer artist quite like a huge, distinctive single, and with “Fancy,” which has amassed 847 million YouTube views to date, Iggy Azalea was summarily unveiled to the world.

Looking back, Azalea says that the “sheer delight and surprise” of “Fancy’s” climb up the charts — which was shared with Charli XCX, then a niche pop star — remains her fondest memory of that year. “I really only expected having an underground career,” Azalea admits. “I remember Charli and I were on the Today Show or Good Morning America, one of those shows that prior to that we had no business being on. We were like, ‘What the fuck are we doing here?’ We loved that we were there.

Then Grande’s “Problem” with a verse from Azalea also hit the Top 10, and “Black Widow,” featuring Rita Ora, impacted rhythmic radio, eventually climbing to No. 3 on the Hot 100. Over the course of one summer, Azalea became one of music’s biggest names; when the 2014 MTV Video Music Awards nominations were announced that July, she received seven, behind only Beyonce for the most of any artist.

Yet as her breakthrough coalesced, so did Azalea’s reputation for fighting on social media. She sounded off on a perceived slight from Nicki Minaj at the BET Awards in June 2014; warred with Snoop Dogg in October; dismissed an (admittedly disgusting) Eminem lyric about her in November; and shrugged off a Q-Tip Twitter thread about the importance of understanding hip-hop history in December. She also continued a back-and-forth with Azealia Banks, a sworn enemy since her mixtape days.

Some of Azalea’s critics took potshots at her on social media based solely on the fact that she was a white woman performing rap music. And while rote misogyny fueled some of the hate, her position as a white woman performing rap music on the biggest stages in America did warrant scrutiny. From the start of her career, Azalea professed a genuine love of hip-hop and sought out mentorship from black producers and collaborators, but repeatedly fumbled when it came time to reflect on her own privilege in the music industry, which naturally fostered skepticism from both artists and fans.

She fumbled on wax too, rapping in 2012, “When the relay starts, I’m the runaway slave-master”; her apology came quickly, with Azalea writing in an open letter, “It was a tacky and careless thing to say and if you are offended, I am sorry.” In a 2013 Complex cover story that ran six months before “Fancy” was released, Azalea said of her perceived “black”-sounding flow, “If you’re mad about it and you’re a black person then start a rap career and give it a go, too. I’m not taking anyone’s spot, so make yourself a mixtape. Or maybe if you’re black, start singing like a country singer and be a white person. I don’t know. Why is it such a big deal?” In December 2014, the same week she received her first Grammy nominations, she was criticized for remaining silent on social media during the nationwide protests against a grand jury’s decision not to indict a white police officer in the death of Eric Garner. “Black people are cool, but black issues sure aren’t huh?” Banks tweeted about her, which started another Twitter showdown.

Azalea’s problem, she acknowledges now, was that she couldn’t distinguish between someone who wanted to start a dialogue and someone who wanted to tear her down. “It’s hard to separate trolling from legitimate criticism,” she says. “When you get thrown into the deep end, you have a natural inclination as a human to defend your character. There were times, in retrospect, where I was way too defensive… where there was so much coming from every direction that I just didn’t have the ability to pick through what was valid and what wasn’t. I just felt like, ugh, I’m walling off everything.

Azalea does believe a large portion of the criticism was gendered, however. “It always is, and always will be a point of frustration,” she says. “But for me as a woman, it is tough to know when to speak about those things and when to stop, because it can kind of make you seem like you’re being a victim instead of taking accountability.” (For her part, Azalea is more careful now to identify and speak on cases of appropriation; during a recent interview with Power 106 in Los Angeles, Azalea was asked about Kim Kardashian West’s braids, and immediately pointed out that some might be bothered by the co-opting a black hairstyle. “That’s definitely something I’ve made mistakes on in the past … there should be an acknowledgement of where it originated from,” she said.)

In the months leading up to the 2015 Grammys, Azalea’s mentions were full of people calling her Grammy nominations undeserved. She finally began to wonder if she needed to take some time away from social media — “It was making me feel physically fucking ill,” she says now — as well as press pause on her career after a nonstop year-and-a-half. Azalea flew under the radar for the second half of 2015, hoping to re-emerge the following year with a new album, but the triumphant return never happened. “Team,” her 2016 electro-rap single that memorably included the line “Go and give ’em all the finger/You gotta set the score right, call it Hans Zimmer,” failed to crack the top 40 of the Hot 100, and three months after the song’s release, Azalea called off her engagement to NBA player Nick Young after he admitted on camera to cheating on her. She says that “personal trauma” added to her overall break from the spotlight; over the following two years, she floated out singles that didn’t make a dent at radio, while alternating between calling out Def Jam for holding her sophomore album hostage and blaming the media for a lack of attention (Def Jam did not respond to request for comment for this story).

Having officially parted ways with Def Jam at the end of last year, Azalea says of her former label, “They were being very supportive and doing the best that they could do, but creatively, I don’t think we were able to understand what it was that I was trying to do moving forward, and I felt a little bit like what they would’ve loved to do is recreate The New Classic. And I get that, from a business perspective. … The only pressure was to keep making pop music when I wanted to get back [to] recording. I said ‘I don’t want to make pop music.’ I remember sitting there saying to somebody with the label, whose name I won’t mention, ‘I don’t want to make music for your 10-year-old daughter anymore.’

Not that she wants to stray too far from pop, or music that young listeners can appreciate. “I love seeing 8-year-olds with their dad in [my] crowds, at their first concert,” Azalea clarifies. “But there needs to be a balance. I’m angry at that time, and I’m frustrated. I have all these things I want to say and they’re very aggressive.” It’s part of the reason why she looks back at her final Def Jam singles — the abrasive dance track “Mo Bounce,” the tropical Anitta collab “Switch” — as solid pop records but incomplete representations of her mindset at the time of their release. “It felt like to put anything out other than addressing the things I’ve been going through is to skip over those things, not acknowledge them,” she says. “And I think they need to be acknowledged. I don’t think I’m able to move on, and I don’t think anyone else is able to move on, until I have an honest conversation.

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