How Iggy Azalea Destroyed Her Own Career

Iggy Azalea first took the music scene by storm when she released the song "Pu$$y" off her debut mixtape "Ignorant Art." The song's music video, which paid tribute to the 1991 film "Boyz N the Hood," went viral and became the stepping stone she needed to eventually top the charts with her summer 2014 hit, "Fancy." The track was released from Azalea's debut album "The New Classic" and earned many prestigious accolades.

"Fancy" became the longest-running No. 1 song on the Billboard Hot 100 chart by a female rapper and received two Grammy nominations. As of July 2014, it was the radio's most-played hit, giving John Legend's "All of Me" a run for its money. "Fancy" boasted an astounding 1.3 million downloads within only six weeks of its release and had been streamed at least 94 million times in the United States within that period.

Needless to say, the song was life-changing, as Azalea told Vanity Fair. "I can't walk down the street anymore, and I have to be very selective when I grocery shop," the former rapper revealed. "I went from having nothing to having everything I could possibly want. It's weird. It's almost scarily easy to quickly forget that you had nothing." Azalea was on a fast track to becoming one of hip-hop's greatest assets, but her career quickly went downhill. Unfortunately, her fall from grace and eventual exit from the entertainment industry had everything to do with behind-the-scenes drama and some calculated chess moves.

In September 2014, TMZ broke the news that a sex tape involving Iggy Azalea and an ex-boyfriend was up for sale. Azalea was set to land a seven-figure deal — as Steven Hirsch, the president of Vivid Entertainment, alleged — but her camp denied claims that she was the girl in the video. Azalea's legal representatives later claimed that the ex in question was a jilted lover. They further said the video had been taken "without her [Azalea's] knowledge or consent" when the retired rapper was still underage (via TMZ).

Azalea's ex-boyfriend, Hefe Wine, who worked as her manager at one point, eventually claimed that he had the right to create and sell the video, per an agreement he reportedly signed with the "Peach Body" rapper in 2009. According to Wine's account, the tape would have been a valid product (as stated in the contract) if he added background music.

When questioned about the alleged tape, Azalea publicly denied its existence, per her chat with Vanity Fair. "Every week I have some sort of crisis that involves the Internet. I do not have a sex tape; I would remember if I had a sex tape," she said. "But if I did have a sex tape it would be completely f***ing fine and my own business." The "Work" rapper and Wine's legal war ultimately came to an end when the duo reached an out-of-court settlement for an undisclosed amount.

As Iggy Azalea's success grew, she began clashing with her peers. First up was "Super Bass" rapper, Nicki Minaj, who made remarks at the BET Awards that seemingly targeted Azalea's alleged lack of writing skills. Minaj denied claims she had beef with Azalea. In response, Azalea said she was "unbothered by anything that 'happened' at the BET awards," per E!.

Azalea also had an altercation with fellow rapper Azealia Banks. The duo's feud started when Banks disapproved of Azalea's Grammy nominations. "That Iggy Azalea sh** is not better than any f***ing black girl that's rapping today," Banks said on "Ebro in the Morning." "When they give those awards out — 'cause the Grammys are supposed to be, like, accolades for artistic excellence, you get what I mean? — Iggy Azalea is not excellent."

A fired-up Azalea took to X to respond to Banks, writing in a now-deleted tweet (via The Guardian), "... There are many black artists succeeding in all genres. The reason you haven't is because of your piss poor attitude. Now! rant, Make it racial! make it political! Make it whatever but I guarantee it won't make you likable & THATS why ur crying on the radio." The response triggered heated discourse on black culture from artists like Q-Tip, Solange Knowles, and Erykah Badu, but Azalea and Banks eventually made up an announced a eventual collaboration. At the time of this writing, this hasn't happened.

Iggy Azalea's first tour, The Great Escape Tour, was scheduled to begin in Fresno, California, on April 14, 2015, and end in Austin, Texas, on May 24, 2015. The arena tour, featuring stops at Staples Center, Target Center, and Barclays Center, was to feature performances by fellow artists Tinashe and Nick Jonas. "I want everything to be right — everything, from the tour book to what someone wears," she said in an interview with GQ. "Even the right faces for the dancers and their attitude. Everything is equally important."

Azalea was only a few weeks shy of starting her tour when it was postponed. The Great Escape Tour was eventually canceled altogether, and according to the "Started" rapper, it was because she "had a change of heart," per Seventeen. "I want to start totally anew, and if I stayed on my tour, that would mean I wouldn't even be able to start working on that until after Christmas," Azalea told the publication. Contrary to Azalea's revelation, It was reported that the tour flopped due to extremely low ticket sales. 

Azalea tried to fill up arenas again with The Bad Girls Tour, which was set to kick off in Hollywood, Florida, in October 2018. The tour featured stops in several states, including Washington, Colorado, and New York, in collaboration with Live Nation. However, it was also canceled shortly before it began.

Iggy Azalea was supposed to headline the Pittsburgh Pridefest in June, 2015, but weeks before she took to stage, she received backlash for posting hateful tweets targeting the LGBTQ community. "When guys whisper in each others ears I always think its kinda homo," one tweet, which was reportedly shared before her fame, read (via The Guardian). Azalea was also accused of posting a racist tweet that said, "Just saw 5 black men get arrested out the front of popeyes. #damn #stereotypes."

Although the creators of Pittsburgh Pridefest, the Delta Foundation, came to Azalea's defense, her performance was canceled. Azalea apologized and took to X to relay the news, partly writing in a now-deleted tweet, per E!, "This has been a difficult decision as I truly support the event and LGBTIQA communities however if eel [sic] my participation at this point would only serve to further distract from the true purpose of the event."

Azalea previously claimed to be an ally of the LGBTQ community in a 2014 chat with Pride Source. While addressing allegations that she was using bisexuality to gain popularity, the "Team" rapper said (via Dallas Voice), "I appreciate women, and I like rapping about them, but in case you thought I was a lame person pretending to be gay, um, I'm not." In the end, she made amends with the LGBTQ community and performed at the 2022 Tel Aviv Pride Festival.

Iggy Azalea and pop sensation Britney Spears released their joint single "Pretty Girls" on May 4, 2015. The song had leaked and only recorded an estimated 100,000 downloads within the first week of its release. "Pretty Girls" was projected to make a Billboard Hot 100 Top 40 debut less than two weeks later, and by May 21, 2015, it had reportedly made a Streaming Songs chart debut at No. 16.

Given the star power of Azalea and Spears at the time, some fans were disappointed by the song's performance. One fan expressed their concern in a Q&A session on X, prompting Azalea to tweet in response (via The Guardian), "It's difficult to send a song up the charts without addition promo and TV performances etc. Unfortunately, I'm just featured." Azalea's comments were thought to be targeted at Spears, and when the singer's fans defended the pop star, Azalea doubled down on her remarks, saying, "My comment is factual, it applies to any song. I don't have to suck the woman's ass***e 24/7 to be her friend, do I?"

While Spears didn't directly engage Azalea, she seemed to throw shade at the retired rapper by referencing her canceled tour in a tweet. "Can't wait to get back to Vegas. So thankful I have shows for the rest of the year to look forward to," Spears wrote. Years later, fans claimed the duo hadn't talked since the 2015 feud, but Azalea revealed that she reached out to the superstar.

When Iggy Azalea first met Nick Young, she was cautious about dating the one-time NBA champion. In fact, Azalea did a proper background check since she didn't like what she saw online. "He just seemed like he was just going out all the time," Azalea recalled in an interview with "On Air with Ryan Seacrest." ".... "'I don't think I want to go out with him.'"

Young luckily passed the background check. The duo began dating — Azalea admitted that she was drawn in by Young's display of wealth — and was set to walk down the aisle after a June 2015 proposal. Trouble began brewing in Azalea's love life when a video of Young admitting to cheating on her surfaced in March 2016. Young's ex-girlfriend, Keonna Green, was also pregnant with his second child.

Azalea and Young eventually split up, and Azalea blamed that for delaying the release of her sophomore album, "Digital Distortion." "I just kind of felt like, on top of me needing the personal time, then feeling, 'I'm single now. I want to have sexy songs. I want to say stuff about being single,'" Azalea said in a chat with People, and continued, "I obviously didn't write that on my [original] album because when I wrote it I was about to get married ... I don't want to go and promote my album and get asked about my relationship that has just crumbled."

Iggy Azalea's sophomore album "Digital Distortion" was scheduled for a June 2016 release date. Azalea initially had 20 songs in the works, but she scrapped them to create fresh material with D.R.U.G.S., a group led by Ty Dollar $ign & DJ Dahi. Azalea and D.R.U.G.S. already had a long history — they helped in the making of her first mixtape, "Ignorant Art."

The former rapper gushed over the group in a chat with Entertainment Weekly. "I just felt like they really understood me so I went back to working with my friends," she said. "It's ["Digital Distortion"] harder than my debut — more aggressive. It's a little bit darker and moodier and there's a bit more of a throwback to some of my older mixtape sounds. But it's got electronic influences used in a rap way."

Although Azalea teased the album before its release, it never saw the light of day. The album's lead single, "Team," only peaked at No. 42 on the Billboard Hot 100 chart. Azalea went on to drop other songs, including "Never Satisfied" and "Hate on It," which never made it to the charts. In July 2017, Azalea revealed that her label wouldn't be releasing any new singles. She eventually changed the name of the project to "Survive the Summer" and compiled it as an extended play, which was unveiled in August 2018.

As an artist, Iggy Azalea often invested heavily in her craft. Case in point: during a 2012 concert in London, England, Azalea was only paid $565, but she used $5,655 to make the gig happen by flying her dancers and dry ice from the United States. While Azalea's efforts were admirable, she didn't entirely stay on top of her finances. In 2016, Uncle Sam came knocking, as she owed $391,056.55 in 2014 taxes.

Azalea took to X to address the claims in a now-deleted tweet, writing (via New York Daily News), "They exaggerate everything. The IRS gave the option to pay them monthly or lump sum. I picked monthly, who wouldn't?" At the time, Azalea was in the news because of Nick Young's cheating scandal, and she tweeted that her financial woes were being used as gossip fodder. "They were hoping some more Nick mess would happen and now that it hasn't and it's getting boring they need to create something else," she wrote. 

Although Azalea is projected to be worth a couple of millions, more money problems followed her when she was taken to court by American Express in 2017 for failing to pay her credit card debt. It was reported that the "No Mediocre" rapper owed the financial institution $299,147.81, which was accrued over two years. Per reports, Azalea had spent $250,000 more than her predetermined limit.

Iggy Azalea experienced a ton of pressure from being an American pop sensation and was driven to having suicidal thoughts. "There were times when I just wanted to quit life — the whole thing, really," Azalea shared on "The Cruz Show." "Sometimes I would drive through the canyons to get to my horses and I'd be like, 'What if I just kept driving off the canyon?'" Azalea stayed in the United States on a work visa, and she eventually took a sabbatical from the American entertainment scene to return to her native country, Australia, as a judge on Season 8 of "X Factor." Ahead of her visit, the former rapper was feeling upbeat about traveling Down Under and reuniting with her family, who lived in Sydney. 

Still, she didn't think of the country as her safe haven, especially since she had moved to the United States in her teens. "I never really consider this my home. I've lived overseas for a decade ... LA is home. It's where I live," Azalea said in an interview with news.com.au. Azalea doubled down on her comments in a chat with GQ Australia, saying (via Just Jared), "Of course I like Australia, but I don't know why people get so offended as it's not my home. I don't miss Australia, not because there aren't great things about it."

Iggy Azalea worked with marketing executive Brian Scully and his publicity team at CHAOS from 2011 to 2014. The team spearheaded her rise to the top, but the former rapper ultimately signed to the London-based company, Turn First Artists, when she found fame. The management company had an elite list of successful clientele at the time, which included Ellie Goulding and Rita Ora.

Scully retained his role as Azalea's publicist, and although it's unclear when the duo stopped working together, in a now-deleted blog post, he wrote an opinion piece on the inner workings of her management. Scully — who has since taken on a content strategy role at STO Building group — opined that Azalea may have become polarizing after the success of "Fancy" due to her new management's different approach to handling feuds. 

He wrote that during Azalea's feud with Azealia Banks, the former rapper was advised by her old management team to "not respond directly and to act gracious when asked about the feud in interviews." However, the laid-back approach took a more chaotic direction under the guidance of her new management. The "Drop that sh*t" rapper was allegedly asked to veer from "'take the high road' to 'jump in the mud pit.'"

Before she became a superstar, Iggy Azalea was already rubbing shoulders with bigwigs in the entertainment scene, like Nas and rapper T.I. Azalea was signed to T.I.'s Grand Hustle Records imprint. The three-time Grammy award-winner was supposed to be an executive producer on her debut album, "The New Classic."

The project didn't materialize under T.I.'s leadership, but the duo still collaborated on several hits, including "No Mediocre" and "Change Your Life." The pair began to butt heads during Azalea's feud with Azealia Banks when record producer Q-Tip had an exchange with Azalea over her alleged appropriation of black culture. T.I. said he tried to reconcile Azalea and Q-Tip, but the former made a response via X.

In a 2019 interview with The Root, T.I., who'd since cut ties with Azalea, said, "I'm still actively looking for another female rapper who can undo the blunder of Iggy Azalea. That is the tarnish of my legacy as far as [being] a [music] executive is concerned. To me, this is like when Michael Jordan went to play baseball." T.I.'s sentiments prompted a response from Azalea, who wrote in a now-deleted tweet (via The Shade Room), "Imagine thinking I was his biggest blunder lmaoooooooo Tip. Sweetie. We have a whole list for you."

Iggy Azalea's feud with singer Halsey began when the latter took to an interview to trash the former rapper. Halsey, who rarely has beef with other players in the entertainment industry, had a bunch of unkind words for Azalea. "There's a lot of people I wouldn't put on my record," she told The Guardian. "Iggy Azalea: absolutely not. She had a complete disregard for black culture. F***ing moron. I watched her career dissolve and it fascinated me."

Up until that point, Azalea had created a culture of slamming her detractors. So, it was surprising when she took the high road in her response to Halsey. "I thought it was a bit of a strange thing to throw that out there, but she's [Halsey] young and I hope she learns maybe to be a bit less judgmental when she's kind of in the same shoes," the rapper told Australian radio show "Small Surgery" (via Billboard). "I'm sure she's getting judged all the time as well by people who don't really know her."

Azalea also seemingly pulled a Mariah Carey by referencing the fact that she and Halsey had never met. Her polite reaction became confusing to fans, many who were used to her savage approach to feuds. While some people argued that she had become calmer with age, others thought she had mastered the art of good PR.

For a long time, Iggy Azalea was accused of appropriating black culture. Critics alleged that Azalea rapped with a signature Black speak, a claim she didn't deny in a 2013 interview with Complex. "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," Azalea told the outlet. "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?"

Azalea amassed a wide teenage fanbase due to her chic choice of style and shattered the myth that she had to fit a black stereotype in a conversation with The Guardian. "To say that rap is a guy in chains and baggy pants popping bottles in a club is stereotyping black culture," she said. "That has never been my aesthetic."

When it comes to creativity, the masses believed the younger generation lacked original ideas and material was being rehashed. It was a claim that the "Sally Walker" rapper dismissed in her chat with The Guardian, saying that "even if something is recycled, it takes a lot to be witty or ironic." Azalea's own words came back to haunt her when she announced her eventual retirement as she revealed she did not like writing songs throughout her career, and it reflected in her work.

Iggy Azalea landed a major record deal with Universal Music Group's imprint Interscope Records in January 2012. The record label, which was co-founded by music executive, Jimmy Iovine, was set to produce her first album, "The New Classic," but the deal ended in mid-2012. In April 2013, Azalea signed to Island Def Jam music group. The joint venture was dismantled by the group's parent company Universal Music Group in 2014, leaving Azalea signed to Def Jam Recordings. Azalea worked with the establishment until 2018 when she moved to its sister company, Island Records.

Azalea later accused Universal Music Group of not paying her dues. "Crazy how in my entire career I was never paid a single royalty by universal music for anything outside of the USA," Azalea wrote in a March 2025 tweet. "They owe me millions of dollars in back pay, that they technically stole from me, as per my contract Iam due payment. The amount owed is in the 8 figure range." The former rapper alleged that she was awarded an $18,000 settlement, which she declined. She vowed to legally pursue the case "until they pay me what they owe" and further accused the conglomerate of exploiting several artists, many of whom were suffering in silence. "Universal music really needs to do better in their treatment of the artists who quite literally earn them millions via intellectual property they had zero part in creating," Azalea wrote.

Master recordings are the heartbeat of musicians' careers — they are original recordings of songs, and whoever owns them can make a ton of money by earning royalties and licensing the music to other entertainment and commercial mediums, such as movies and advertisements. While artists like Jay-Z own their masters and vow to never sell them, others have put them on the market for a big payday. In 2024, half of Michael Jackson's music catalog (including master rights) was sold to Sony for a reported $600 million. Similarly, "Sorry" singer Justin Bieber sold his music rights to Hipgnosis Songs Capital (including masters shares) in 2023 for a reported $200 million.

In 2022, Azalea joined the long list of artists who parted with their masters when she sold her music catalog to Domain Capital in a reported eight-figure deal. Azalea also gave away publishing rights to her most popular hits, "Fancy," "Black Widow," and "Problem." When the news broke, a fan in an X comments section was worried that she'd landed a bad deal like Taylor Swift — Swift's masters were sold to her nemesis, Scooter Braun, but she's since regained the rights. In response to the fan's sentiments, Azalea replied in a since-deleted tweet (via Just Jared), "Taylor did not profit from that sale. I sold a portion of my catalog to who I wanted, for an amount that means I don't have to work another day in my life."

In October 2022, Tory Lanez announced on X that he would be an executive producer on Iggy Azalea's next album. That same year, the duo was also rumored to be dating, a claim Lanez seemed to confirm when he titled a song after Azalea using her official name, Amethyst. The 2025 release, "9$IDE x Amethyst," featured the lyrics, "It be nights I want to talk to Iggy, but she blocked me / Amethyst, if you ever hear this sh*t, shawty, call me."

When Tory Lanez faced a legal war against rapper Megan Thee Stallion after a shooting incident, Azalea wrote to a judge to vouch for Lanez (official name, Daystar Peterson). "I would not write to you on behalf of an abuser,' the letter said in part, per Daily Mail. "I've never encountered this jealous, rage filled person he's accused of being. I know him to be someone who's always bursting with happiness."

Azalea's show of support wasn't taken kindly by the public, most of whom were supporting of Megan. One upset fan took jabs at the former entertainer, writing on X, "Girl, that's why you fell off and the music ain't selling. This is so embarrassing and disgusting of you." In a now-deleted tweet responding to the backlash, Azalea stated that she and Lanez had not been in contact for a long time. She further revealed she was blindsided when her letter became public and additionally voiced her support for prison reform. 

After releasing numerous bodies of work, including albums, mixtapes, and extended plays, Iggy Azalea finally hung up her boots in January 2024. The former rapper announced her exit from the music industry in a lengthy post on Facebook, writing in part, "I know a lot of people have this idea that I was "bullied away from music" and that's something I've always laughed at because I'd never be bullied out of anything! In fact, I'm too stubborn. I think I've even resisted changes within myself at times, purely because I don't like being viewed as someone who quits." At the time of her announcement, Azalea was in the process of working on her fourth album, although she'd previously tweeted that her third album, "End of an Era," was her last. She sadly told her fans that she wouldn't be completing the project.

Beyond music, Azalea wasn't running out of options to pursue since she'd had other sources of income that supplemented her revenue in the past. Back in 2012, she signed a modeling contract with Wilhelmina International, Inc., a company that represented top talent in the business at the time, including singers Fergie and Estelle. She also appeared in a Super Bowl commercial for the energy drink brand Monster, with whom she collaborated on launching a set of headphones. Azalea dipped her toes into entrepreneurship by launching her fragrance Devil's Advocate in 2021 and having a short-lived but thriving OnlyFans career.

Following her retirement from the music industry, Iggy Azalea announced she would be hosting the "Mother Knows Best" podcast in partnership with The Volume. She also ventured into the cryptocurrency arena with the launch of her own crypto token, $MOTHER. Azalea was introduced to the cryptocurrency business by her brother, and she found herself curious about its intricacies during the 2021 non-fungible token (NFT) boom.

Her token, $MOTHER, is unlike other celebrity tokens, as she explained in a chat with the "Rapid Response" podcast (per Fast Company). But when you use the word utility in crypto, everyone's like, 'Ew, it's a dirty, boring word,'" Azalea said. "I want the fun of a meme token and try to have that, the community of that, and the chaos of that combined with some real-world usage and utility."

Azalea uses telegram to build her own $MOTHER or Mother Iggy community — the name $MOTHER is in itself an ode to motherhood — and in late 2024, she took the game a notch higher by debuting an online casino dubbed Motherland. The gaming and betting platform uses $MOTHER. At the time of writing, Azalea's token is priced at $0.0123.

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