They made about six songs, Lee recalls, including an ’80s jazzercise record titled “U Ain’t My Daddy,” where Iggy lectures a possessive dude: “S’posed to be my man/but you act like my babysitter,” she raps. Her blaccent is thick, flow disjointed, but the musical style is much more J.J. Fad than T.I., a distinct departure from the Southern rap imitations that eventually became her signature.

In January 2009, Iggy and Williams moved to Atlanta, where their relationship ended. Details later became public, after Iggy filed a lawsuit against Williams in 2014, accusing him of copyright infringement over those early recordings, which Iggy claimed he’d stolen from her laptop and released illegally. In court testimony, Iggy described Williams as her “first ever serious boyfriend,” said they lived together and that they broke up in 2009 after a “massive, massive fight” on Valentine’s Day. Williams, in his testimony, couldn’t recall the fight. He claimed that Iggy reneged on a management contract when she signed to a major label. A judge later ruled his contract invalid.

In the midst of her teachings, Iggy’s business dealings got messier. Around 2008 in Houston, through Mr. Lee, she also met Jon Jon Traxx, a producer who says he connected her to music executives, choreographers and prominent producers over two years. Last year, he filed a $1.5 million breach of contract lawsuit, which was settled this past July. Jon Jon Traxx declined a request for an interview, stating via email: “Thanks for reaching out, but I’m not doing any interviews that has [sic] anything to do with Iggy.”

A pattern began to emerge: Iggy had fragments of talent and a ton of audacity. Her talent mattered less than her looks. The producers she worked with saw her more as a total package: an edgy white female rapper with pop appeal. But Iggy emphatically protested whenever she was steered in the direction of a Fergie, Gwen Stefani or Britney Spears.

One of the first songs she recorded in Atlanta was “Nothing Like Me,” a bargain-bin version of Spears’s “Womanizer” that features no raps, just her digitally enhanced vocals. When the song and music video leaked in 2014—and sounded nothing like “Fancy,” where Iggy proclaimed to be “in the murda bidness”—it seemed to confirm her status as a rap poseur.

Part of Iggy’s grab for authenticity was currying support from credible rappers. Around 15 years old, she reached out to Backbone, a member of the Outkast-affiliated rap crew the Dungeon Family, on MySpace. Iggy would send him videos of herself rapping in her bedroom and messaged him so often that Backbone gave her top-10 placement in his MySpace profile. Years later, when she made it to Atlanta, she suggested they meet in person.

For about two weeks, Iggy had something of an apprenticeship with Backbone, who stresses that “nothing inappropriate” happened. He didn’t sign her to a contract or make promises, he says. But he did teach her about bars and song construction. He introduced her to his grandmother, and Iggy ate fried chicken for the first time. She marveled at the plaques on his wall and told him, “I want this.” Their studio sessions, Backbone describes, were more like a “proving ground,” where Iggy would sit around with other artists—the lone woman rapper—and workshop selections from her rhyme book.

They never recorded a song, but her hustle and knowledge of hip-hop impressed him. “There was definitely talent there. She could rap over Southern beats, New York style beats, California beats,” he says. “But her accent was so thick, people couldn’t see her becoming a rap star.”

A friend of Backbone’s recently expressed shock that he’d had a hand in Iggy’s success. “People still look at it like she’s not talented, but she’s one of the greatest female MCs there is,” says Backbone. “I’m going on record with that.”

Networking around Atlanta led Iggy to Polow, who figured that as a pop-rapper, she could lure a broad base—more specifically, black men. “You’re gonna attract the black guys, when you got an ass that big,” he told her. At the time, Iggy had been working out furiously, up to four days a week, and taking performance training as part of consultations with Atlanta’s Marvelous Enterprises Artist Development Center, a service that promotes itself as “a superstar-training site.”

Besides seeing Iggy’s potential as a cash cow, strangers were willing to give a young Australian girl a chance, largely off sight—the sort of latitude that white and pretty privilege affords. Still, four years into her tutelage, Iggy’s peers (Polow included) were unimpressed with her raps, which again posed a slight issue for an artist who wanted to be respected as a rapper.

“It isn’t like when you meet an artist and they’re a few songs deep. It’s like, oh no, you really have to learn how to rap,” says a former colleague of Iggy’s who asked to remain anonymous. “Literally everybody told her she would never be a rapper, so it became something to prove, in a way that, to me, was very detrimental. She wanted people to be like, ‘Yes, Iggy the MC!’

The intro to Iggy’s breakout song “Pu$$y” comes from Eddie Murphy’s 1992 film Boomerang, released when she was two years old. “You are going to turn down a pussy like this? Staring you smack in the face?” Grace Jones taunts, repeating the word. This was many people’s first introduction to Iggy, in late 2011, the same year that a flash-in-the-pan white rapper named Kreayshawn released her popular song, “Gucci, Gucci.” The brass and coolness of “Pu$$y,” which appeared on Iggy’s 2011 mixtape Ignorant Art, along with her blatant sex appeal—she established her signature look: cat eyes, red lips and a super high ponytail—spelled potential.

Iggy was skilled at conceiving creative campaigns, including mixtape artwork and videos like her freestyle “Two Times,” where she presents herself spread eagle as graphics flash across her crotch. Iggy thought up the “Pu$$y” treatment, based on Ice Cube’s 1995 film Friday, and chose to shoot the video in the middle of the hood, on Slauson Avenue, a part of LA known for Crip activity. This was, in part, for the white-girl-in-the-hood aesthetic (“White bitch down Slauson/Gangstas faint,” she rapped on Ignorant Art), and because Iggy could film in her friend’s grandmother’s house for free. She edited the video herself using the raw footage given to her by its director, Falkon.

Immediately, there was pushback over the video’s imagery of a black boy seen draped over Iggy’s shoulder while she rapped about pussy. The Bossip headline: “Another White Girl Rapper, But Why The Black Kid In This Video?” When asked about the criticism, Iggy responded with irritation, telling Dazed and Confused in 2012, “Those people can fuck off. They’re like, ‘Oh, she wants to be black,’ or, ‘She doesn’t give Australia props.’ All that crap. What does that even mean?”

This confusion persisted. Iggy had a visible love for hip-hop, but she seemed to be living out a fantasy. Whenever she speaks about her obsession with hip-hop, she recalls falling in love with 2Pac’s “Baby Don’t Cry” and hanging his posters on her wall. She cites Aquemini as her favorite Outkast album, talks about studying rap videos on YouTube (without fully grasping the context of the songs), and about writing her own sexually explicit raps at 14. As a teen, she traveled to nearby Lismore to witness rap cyphers, and her first Instagram picture, posted in February 2012, is a shot of Biggie on the cover of XXL. She became a student of hip-hop. But becoming a rapper would take more than that.

Developing her rap voice—a distinct high-pitched karaoke effect, like a Lonely Island parody—was part of the illusion. When asked about Iggy’s success in a 2015 interview with Sway in the Morning, Eve, the rapper, said: “The tone. The blaccent. It would be dope to hear her with her swag. What are you? Who are you? What is that?”

At face value, the accent, a product of Iggy’s teachings in the South, seemed like a callback to a familiar, grotesque costume. In a 2016 article, “How Iggy Azalea mastered her ‘blaccent,’” the Washington Post cited a paper by linguists Maeve Eberhardt and Kara Freeman in which the authors contend: “Linguistic minstrelsy is a form of ‘figurative blackface’, in which white users of African American English (AAE) do not literally darken their skin with make-up as in turn-of-the-century minstrel shows, but in essence perform in blackface, drawing on linguistic and other symbolic elements that signify racialized ideologies to a wide US audience.”

Iggy, coming from Australia, didn’t quite understand her caricature. As a white artist in a predominantly black space, however, she studied enough to anticipate the criticism that accompanies every white rapper, from Vanilla Ice to 3rd Bass, Eminem, Fergie, Kreayshawn and Macklemore. She told Gawker, in a 2012 interview, “I don’t ever want to be the person that takes something and doesn’t give homage to where it’s from.” Though Eminem wasn’t exempt from backlash—he had to apologize for using “nigger” in an old song—what saved him from extensive lashings was the perception that he had a gift, which has the power to outweigh ignorance at any cost. Eminem was also fortunate enough to come up before the reactive news cycle that dramatizes plays in real time, though there were hip-hop magazines (XXL, The Source, Vibe) that questioned his credibility.

More recently, what saved Macklemore was a level of self-awareness. He excessively atoned for his sins in public and wrestled with his identity in songs, no matter how grating. Other white rappers wisely chose not to engage with critique, to focus on their music, or play the background. Iggy, on the other hand, was a foreigner thrice over—white, a woman, Australian—who responded to nuanced critiques with defensive retorts and had far fewer people convinced of her talent. Many of her issues seemed to stem from the desire for an assimilation she could never achieve. She could fake being American, sure, but she could not fake being black American. Not without pushback.

When T.I. entered the picture in 2012, in the middle of her negotiations with Interscope Records, it was an opportunity for her most legitimate endorsement. Iggy landed a management deal with his label, Grand Hustle, and T.I. tagged along to her interviews, co-defending her cultural crimes. Meeting him was a turning point for Iggy’s career to the extent that it influenced the contentious, enunciated Southern style of rap on her debut album, The New Classic. The connection allowed her to push the hardcore persona she desired from the start. Finally, she could rap about haters “shootin’ at me with a tommy gun” and posture like her male rap peers.

Fabrications aside, her debut album contains a smart balance of street and mass appeal, though Iggy’s flow leaves a noticeable stain. When paired with proficient MCs, her defects became glaring. On “Runaway,” a track on her 2012 mixtape Glory (which T.I. executive-produced), Pusha T’s raps have a clean luster in comparison to Iggy’s errant delivery.

After partnering with T.I., Iggy phased out some of the creators behind her earlier, stronger material, according to the collaborators I spoke to, one of whom cited her rejection of an Interscope deal as one of several questionable career decisions. To the people around her, the cloning of T.I.’s sound felt forced. Kareem Chapman—T.I.’s assistant at the time—signed Iggy to a management contract in partnership with her ex, Maurice Williams. Chapman jokes, “2Pac didn’t get gangster till he played Bishop in Juice. She got gangster when she joined Grand Hustle.”

From “Pu$$y” onward, the criticism grew. On her 2011 song, “D.R.U.G.S.,” Iggy borrowed a line from Kendrick Lamar’s “Look Out for Detox,” where he raps, “When the relay starts, I’m a runaway slave.” On her version, Iggy flips it to: “When the relay starts, I’m a runaway slave/Master, hitting on the past gotta spit it like a pastor.”

In an open letter posted in response to the subsequent criticism, Iggy wrote: “Kendrick Lamar is one of my favorite artists and I loved his song ‘Look Out for Detox’ so much I decided to do my own version of it last year. The lyrics I wrote follow the original version closely; One lyric in particular has offended a lot of people and for that, I apologize.” Iggy’s collaborators say she often used ghostwriters (specifically, black artists and songwriters) and that one of them penned that line. Her team didn’t anticipate such a big blow-up. Iggy continued to commit infractions and perturb her respected peers.

In 2014, Q-Tip took up the cause of educating Iggy via Twitter about white privilege and hip-hop (read: black) history. Iggy responded with a tweet: “i find it patronizing to assume i have no knowledge of something I’m influenced by, but I’ve also grown up with strangers assuming that.” The next year, on stage at the Soul Train Awards, Erykah Badu described Iggy’s music as “definitely not rap.” In response, Iggy tweeted about being discredited for her accomplishments. In January 2016, she got into another Twitter fight with Talib Kweli after Macklemore name-dropped her in his song “White Privilege II.” Kweli tweeted “Fuck Iggy Azalea, adding: “She’s disrespected hip hop culture one too many times.” Iggy responded by pledging her love of hip-hop and suggested Kweli “come to grips” with the genre’s expansion. Months later, she was chastised when she took offense to white women being called “Becky.”

Iggy’s cultural blind spots were most remarkably transparent through her feud with Azealia Banks, an erratic rapper from Harlem who welcomed the friction. Banks was quick to question Iggy’s cultural affixation and hated her ability to wear the costume of rap without any of the struggle. She referenced Iggy’s old racist tweets and repined that her own voice got lost in the madness of Iggy mania, in the ultimate show of white privilege.

Both Iggy and her publicity team had a philosophy, at first, to ignore the backlash. “Especially with Azealia Banks,” says Brian Scully, Iggy’s publicist from 2011 to around 2014. (He says Iggy received no formal media training at the time.) “She knew that wasn’t a public argument she wanted to get into, especially being new. Obviously, at a certain point that strategy went to the wayside.” He adds, “Nobody really ever had control over her.” Certainly, autonomy is a good thing in an industry that tries to restrict women’s voices, but ultimately damaging under the circumstance of repeated ignorance.

Scully thinks Iggy’s social media strategy shifted for the worse after 2013, when she started working with a UK management team, Turn First Management, which counted Rita Ora as a client. At that point, Iggy relocated from the U.S. to Wales to record The New Classic. “The UK team was much more guarded,” says Scully. “Because of all the controversies, because she was a loose cannon to an extent, they wanted to corral her in a bit.” (Iggy’s former manager Sarah Stennett declined to comment.)

What made Iggy’s gangster aesthetic more tragic was her increasingly tone-deaf approach. The more defensive she became, the more she centered her work around a white female struggle, the more the critiques of her deficiencies devolved into apathy. Imprudently, she took to using her whiteness and sexism as a shield. “The Rolling Stones go to America, play ‘black’ blues music, and nobody has a fucking issue with it or thinks it’s weird,” she told Complex in 2013.

Rather than seeing race as an issue, Iggy focused on the trend of women in rap being over-policed and accused of not writing their own rhymes, while in the process overlooking how artists like herself and Macklemore hold a broader industry advantage, even as they feel like outcasts in their field. To push forward the idea that no one can borrow from another culture is unproductive, when the issue revolves more around the nature of profit, preservation, and which party gets to capitalize while the other is traditionally marginalized. As Jeff Chang explained in a 2014 essay for The Guardian:

Is hip-hop only for black people? It is an irrelevant question. Few black hip-hop artists have ever made that argument. But to say that hip-hop begins as black culture made by black people is not just a statement of fact, it is an acknowledgment of the master key that opens the door for everyone, the way a clave unlocks a rhythm.

In Iggy’s case, there’s an entire continent of disconnect. Of course, she would use American rap (the most accessible genre) as an aspirational model, having few hometown templates to mirror, and, naturally, she would feel sidelined in a men-dominated industry. Above all, she knew hip-hop could make her money.

“I think Iggy genuinely bought into and enjoys hip-hop because the profit model was something not commonly seen in Australia,” says Dr. Timothy Laurie, a communications professor at the University of Technology Sydney. “What’s clear is that she finds, within African-American hip-hop, examples of femininity that she strongly identifies with that she doesn’t identify with in, say, white femininity in Australia.”

Laurie points to issues with white Australian artists failing to grapple with their white identity in an indigenous setting, let alone American racial politics. “I don’t think that the lack of intersectional thinking is particularly unique to Australia,” he says. “White Australians might be more likely to place the emphasis on ‘Australia versus America’—David and Goliath—rather than on other cultural differences.”

The nature of acceptance in hip-hop continues to evolve just as the conversations around appropriation remain stagnant, with little movement outside of familiar talking points. There’s a sense that nuance has gotten lost; in a recent essay for Current Affairs, for example, Briahna Joy Gray argues in favor of the terms “economic exploitation” and “cultural disrespect” (versus appropriation) to emphasize how much “non-white cultural products are often considered more valuable or esteemed when performed by whites.”

While the genre’s expansion has become a point of pride, Iggy’s ascent is the worst-case scenario of a white artist from a foreign country seemingly trying to wrest culture away—and getting by on mediocrity—in the service of living out a fantasy. She also, in many ways, represents a portion of hip-hop fans who care less about appropriation and credibility than older generations do.

The necessity to rap with competence has changed, to that end, with paint-by-numbers rappers of all kinds simultaneously making popular radio hits while facing critique. No one is exempt from clowning. There’s an infamous viral video of Iggy rapping the lyrics to her song “D.R.U.G.S.” in gibberish, and another video of her freestyling on Sway in the Morning in 2013—which later turned into a meme. Instead of off-the-cuff rhymes, Iggy rapped pre-written lyrics from her song “New Bitch,” failing the hip-hop quiz.

As Sway in the Morning’s longtime host and hip-hop sage, Sway Calloway considers himself a purist. He’s protective of tradition while acutely aware of a losing grip on ownership—a fear that’s manifested itself through Iggy.

“When she went through the controversy with Q-Tip, she could’ve handled it differently, instead of getting into a public debate. From that point on, I tuned out,” says Sway. “I also think people gon’ have to get a grip with the fact that rap isn’t just ours no more. There are people all over the world expressing themselves through this art form that don’t know the basic fundamentals. People who have nothing to do with the culture can walk in, take full advantage of it, then walk away and get away with it.”

Iggy didn’t have much of a clean getaway, because her ascent dovetailed with the dawn of the thinkpiece era—the proliferation of essays that were part of a broader, swelling cycle of online criticism around race and identity. As Slate surmised in 2014, the speed and quantity of criticism gave off the impression that there were “more thinkpieces published nowadays than at any previous point in history, as print publications with limited column inches have given way to Web outlets hungry for content.”

When Forbes published an article in 2014 titled “Hip Hop Is Run By a White, Blonde, Australian Woman,” the site was forced to change the headline to “Hip-Hop’s Unlikely New Star: A White, Blonde, Australian Woman,” after angry feedback from readers annoyed with the thought of a white woman running hip-hop. That same year, Salon published “Iggy Azalea’s post-racial mess: America’s oldest race tale, remixed,” and The Daily Beast wrote “The Cultural Crimes of Iggy Azalea.”

Her mere presence offended people. “Iggy was in the right place and the right time to become the object of that specific critical gaze,” says Robin James, an associate professor of Philosophy at UNC Charlotte who covers pop culture. “But she should be subject to that criticism. It should be an uncomfortable space for a white artist to appropriate black music. It’s only because of her white privilege that Iggy can be in that uncomfortable space but not have it get in the way of her career.”

From the outside, the barrage of criticism did seem to affect Iggy’s livelihood. In March 2015, she cancelled her Great Escape Tour. While Billboard reported low ticket sales, an AEG Live rep claimed the tour was “selling well.” Chris Anokute, the A&R who signed Iggy to Island/Def Jam in 2013 and now works at Epic Records, thinks her label “overshot” and overestimated Iggy’s potential to book arenas based on one album’s worth of material. (Iggy herself said she just needed a break.) Other deals simply disappeared. T.I. severed ties, and according to Wilhelmina Models, Iggy is no longer signed to the agency, though a rep didn’t respond to a request for further details.

Amid her career wreck, Iggy’s love life seemed ever precarious. High-profile relationships with rapper A$AP Rocky and then Lakers guard Nick Young made her a gossip-blog regular, disposed to judgment about the optics of a young white woman seen dating solely black men and toeing the line of fetish versus preference.

With Young especially, the relationship was highly publicized, perhaps tactically, which included a GQ spread and openness about their engagement. When the couple moved into a home in LA, it made the blogs, and when Iggy moved out, that did, too. In June 2016, she and Young broke up, months after his Lakers teammate secretly taped him confessing to cheating and the video leaked online, another source of embarrassment. Since then, Iggy has been spotted with rapper French Montana.

None of the singles that Iggy has released in the past year—“Team,” “Mo Bounce,” “Switch”—have come close to the aggravating allure of “Fancy.” In that time, she’s vented about the status of her album on Twitter at various points, including on July 8, when she reiterated that Digital Distortion had not been cancelled and that she was unhappy with all the delays. In yet another setback, a planned collaboration with her nemesis Azealia Banks—an opportunity for a music moment slash promotional buzz—has gone awry. A delayed album is far from an unusual scenario in the music business, but a telling one nonetheless.

“I don’t think [Iggy’s issues] have anything to do with people hating Iggy or thinking she’s corny,” says Anokute, her former A&R. “The songs just weren’t good enough.” Verse Simmonds, the co-writer of “Switch” and “Mo Bounce” is confident in Iggy’s evolution and does his job of selling the project. “Every producer I know wants to work with her,” says Simmonds. “I think people are gonna be surprised with her lyrically this time around. That definitely was a major concern of mine. But I don’t think we look to Iggy Azalea to be the greatest MC on Planet Earth. She is a pop rapper.”

As much as her life has been an open book, it’s been a challenge to get to the heart of who Iggy really is, behind the performance. As her former colleague puts it: “There has to be a narrative as to why I’m still fucking with you.” And if it isn’t outstanding music or a lovable persona, there isn’t much left to grab onto. “She is too private and at times comes off flat. I think they need to focus more on giving fans a 360 real-time view into her life,” suggests Holly Baird, a veteran publicist and crisis manager. “Most of her issues are racial appropriation or flat-out inappropriate. The time for her to address who she is and what she believes in is now.”

That Iggy has had a revolving door of mentors, without a core group from the beginning, may speak to her weakened career and the risk she presents, as a contentious white female rapper who’s best known for not being a very good rapper. Twenty years ago, she may have very well disappeared from the public eye, with one big song to her name and not much else. But as much as the outrage cycle has cursed her and possibly killed her career, she’s also been fortunate enough to avoid being cast as a complete one-hit wonder, in an era where social media lets even the most ungifted of ghosts linger. What people want from her isn’t great rap. It might just be a solid pop song. It might be nothing at all, or to simply embrace the power of mediocrity.

“She came out at a very interesting time,” Polow notes. “We’re living in a time where wack is actually average. So even if she’s wack, at worst she’ll be average.” Besides, he adds, “How many artists do we come to love who aren’t really that good?”