It’s tax season, a relatively stressful and miserable time of year unless you’re obscenely rich — and, this year, it’s especially terrible if you’re Sigur Rós. Late last month, the Icelandic space-rockers were rocked by tax-evasion charges from their home country’s government, just a few weeks after being cleared in a previous investigation. Over $6.5 million of the band’s assets have effectively been frozen pending trial.
The news might have seemed a little shocking and humorous — they’re a popular band, sure, but who knew that a band mostly known for singing in a quasi-fictional language had over $6.5 million lying around? — but there’s a long history of musicians failing to pay taxes for one reason or another and having to pay the piper when the IRS (or, in Sigur Rós’s case, their country’s version of the IRS) comes calling. We’ve compiled an assuredly incomplete but as comprehensive as possible list of artists over popular music’s history who have been nabbed for, accused of, or attempted to beat tax-evasion charges, including what they owed and what the aftermath to date has been.
Two notes: First off, there have been more than a few musicians who have craftily avoided taxes through foreign tax shelters and such. They’ve been excluded from this list for reasons of congruency — this is a list of allegedly felonious behavior, rather than rich people knowing how to cheat the system because they are rich. Second, pay your taxes — always. Just do it. Their talent, fame, and considerable coffers aside, you don’t want to end up like any of these people.
How much did she allegedly owe? More than $16 million
What happened? The Spanish government charged the Colombian singer late last year with dodging taxes over a three-year period, 2012 to 2014, in which she allegedly claimed the Bahamas as her official residence although living in Spain. Shakira’s lawyers maintained her innocence, stating that she wasn’t a legal resident of Spain during that time period; she’s due in court this June and faces possible jail time if convicted.
How much did he allegedly owe? $728,536
What happened? The Philadelphia rapper failed to file tax returns from 1999 to 2005, save for one $10,000 payment in 2001. After pleading guilty, he was sentenced to two years in prison in 2012, along with a year of supervised release in which he was expected to repay the back taxes along with any subsequent interest and penalties.
How much did she allegedly owe? More than $1 million
What happened? In 2006, the legendary late singer was forced to put one of her New Jersey homes on a sheriff’s auction block due to the back taxes owed. And years after her passing, Houston’s estate continued to run afoul of the IRS: Last year, the estate settled with the organization for more than $2 million over what the IRS claimed to be an $11.7 million bill.
How much did he allegedly owe? $32 million
What happened? The IRS seized Nelson’s assets in 1990 — including properties in six states — as the singer claimed obliviousness due to bad advice and mismanagement from past accountants. After his estate was cleaned out, the country legend still owed $16.7 million, over $10 million of which was in interest and penalties; in 1993, he settled with the agency for $9 million, including $3 million that had already been paid off.
How much did he allegedly owe? Over $3.2 million
What happened? While serving a sentence for sexual battery in 2006, the Louisiana rapper was also convicted of evading $271,000 in taxes, resulting in a yearlong jail sentence. Did he learn from the experience? Not quite: In 2017, the state of Louisiana claimed that he owed more than $2.9 million in back taxes from 1997 to 2002. The case is set to enter trial stages this year; last month, he placed blame on his record label and management team in court docs, claiming he wasn’t aware of his tax filings until 2003.
How much did he allegedly owe? $110,000
What happened? The late rock-and-roll legend pleaded guilty in 1979 to not paying taxes on earnings paid out in cash from live shows throughout the decade; he was sentenced to four months in prison and 1,000 community-service hours.
How much did he allegedly owe? $1.1 million
What happened? Long before Ja Rule dabbled in the music-festival scamming business, he was busy scamming the IRS. In 2011, he pleaded guilty for not filing tax returns from 2004 to 2008, eventually receiving a 28-month jail sentence on top of time that he was already serving for attempted criminal possession of a weapon the previous year. He was released in May of 2013.
How much did he allegedly owe? Almost $6 million
What happened? Anthony’s first brush with tax troubles was in 2007, when a court ordered him to pay about $2.5 million in back taxes; he wasn’t prosecuted because the fault lay with a professional accountant who allegedly led the singer to believe his taxes had been filed. In 2010, he was hit with another $3.4 million tax lien on a New York property owned by him and then-wife Jennifer Lopez; his rep subsequently claimed that an agreement between Anthony and authorities had already been reached.
How much did he allegedly owe? $106,000
What happened? After being accused of not filing taxes from 2004 to 2007, the Wu-Tang Clan rapper pleaded guilty in 2011 and wrote a check for a final $40,000 restitution payment, avoiding jail and a blot on his record through a conditional discharge.
How much did she allegedly owe? $400,000
What happened? The R&B veteran was hit with a tax lien at the top of 2019, stemming from unpaid taxes in 2007 and 2008 — but it’s already being taken care of, according to docs filed in the Georgia court system earlier this year.
How much did he allegedly owe? $1.3 million
What happened? The late icon had to make amends after it was revealed that he was delinquent in property taxes on his owned space in Chanhassen, Minnesota (which includes the famed Paisley Park property). And his estate’s tax troubles have only continued after his death: In 2017, they were forced to pay a $100 million estate tax as a result of presumed business mismanagement and poor planning.
How much did he allegedly owe? More than $2 million
What happened? The Prince of Darkness and his wife, Sharon, were hit with two tax liens in 2011 from unpaid taxes in 2007 and 2008. They slowly paid it off though.
How much did he allegedly owe? $7.72 million
What happened? After being hit with the hefty bill for unpaid taxes in 2002 and 2009, Weezy forked over the money to the IRS following the agency’s threat to seize his $11 million Miami mansion. Last year, he gave Jay-Z credit for helping him break even: “He’s a real friend, y’all.”
Mary J. Blige
How much did she allegedly owe? Over $4 million
What happened? In 2013, the R&B singer was hit with a tax lien of over $900,000 from the state of New Jersey, along with an alleged $3.4 million in federal back taxes. The state lien was paid off, but it doesn’t look like her troubles have ended since: After filing for divorce in 2016, it was reported the following year that the R&B singer cited an alleged $6 million-plus debt in filed docs.
How much did he allegedly owe? $1.3 million
What happened? After filing for bankruptcy in 2013, the pop singer’s publicist claimed that the filing was “positive” and mainly due to back taxes from 2003, back when he was a teenager. He settled the debt in 2014.
How much did he allegedly owe? $20 million
What happened? The R&B singer’s two decades of legal troubles obviously go without saying, but even beyond the allegations of sexual abuse, his history with tax delinquency is just as well-known. In his 19-minute SoundCloud rant “I Admit” released last year, he claimed that he owed the IRS the aforementioned sum, which he’s allegedly been unable to pay since, among other expenses like child support and the bond for his two recent jail stints.
How much did she allegedly owe? Nearly $500,000
What happened? The rapper was hit with multiple federal and state tax liens last year; unable to pay her debts, she filed for bankruptcy and allegedly offered her foreclosed home to help pay the debts — despite having no stake in the property.
How much did he allegedly owe? Returns on more than $3 million in earnings
What happened? After pleading guilty in late 2012 for failing to file in 2007 and 2008, the rapper was sentenced to four months in federal prison in 2013 — a sentence that carried leniency for $718,000 in back taxes that were paid prior to sentencing.
How much did he allegedly owe? $3.1 million
What happened? Last year, the Public Enemy member and onetime reality-TV-show fixture was accused of failing to pay taxes for a whopping ten years — much of the debt coming from 2007, while he was filming season two of Flavor of Love. No word yet on the outcome.
How much did he allegedly owe? $1.2 million
What happened? The rapper was hit with a tax lien in 2014 — which, in a rarity for this list, he promptly paid off. Good looking out, Flo Rida.
How much did he allegedly owe? Almost $7 million
What happened? Tax liens have plagued Nas for most of this decade: Back in 2011, he allegedly owed nearly $6.5 million to the IRS. Last year, he was hit with two more from the state of Georgia, totaling over $300,000. So far, he’s reportedly scraped together more than $3.5 million to avoid jail time.
How much did he allegedly owe? $1.2 million
What happened? Richie was hit with a lien in April of 2012 — right around tax day, naturally. “I was recently made aware of the situation by my new team, and it’s being handled immediately,” the singer said in a statement through his publicist at the time.
How much did she allegedly owe? Over $600,000
What happened? Back when the now perpetually struggling rapper was on top of the charts — specifically in 2014 with The New Classic and its megahit “Fancy” — she wasn’t exactly on top of her taxes. In 2016, she got hit with multiple tax liens from the year in question. Of course, Iggy hit back against the reports on Twitter at the time.
How much did he allegedly owe? More than $7.6 million
What happened? Even opera singers get the tax blues: After an Italian court rejected his claiming of notorious tax haven Monaco as his place of residence in 1999, he agreed to pay a significant chunk of back taxes the following year, related to charges of tax evasion from 1989 to 1995. He was eventually acquitted in 2001.
How much did she allegedly owe? Almost $7 million
What happened? This one is a little wilder than the rest: After filing for bankruptcy in 2013 and effectively discharging her debt to the IRS (which the agency contested), Warwick went on to sue the agency herself. Six years later, the case is still ongoing and recently had its trial date suspended thanks to — wait for it — the recent government shutdown.
How much did she allegedly owe? Roughly $2.3 million
What happened? After pleading guilty to tax-evasion charges in 2012, the singer and rapper served a three-month sentence in a minimum-security prison the following year.
How much did she allegedly owe? Unclear
What happened? Many artists on this list could (or have tried to, anyway) chalk up their debt woes to faulty accounting or a change in management. But Simone very intentionally did not pay taxes in the United States — effectively a protest against the Vietnam War — and after finding out in the early 1970s that the country had put out a warrant for her arrest, she decamped to Barbados and never returned.
How much did he allegedly owe? Over $300,000
What happened? Forget being sorry for 2004 — the former American Idol winner also found himself apologizing for 2009 back in 2012, when he and his estranged wife were hit with a federal tax lien. It was the second time within five years, too; back in 2008, he was hit with a $200,000-plus property lien from the state of Alabama.
How much did he allegedly owe? $2.4 million
What happened? Back in 2016, Nelly was hit with federal and state tax liens for unpaid taxes in 2013 — and, in a very late-2010s twist, the internet tried to come to the rescue. The #SaveNelly hashtag originated, with internet denizens boosting streams of his indelible single “Hot in Herre” to attempt to raise funds for the rapper to pay off the debt. His streaming numbers did see a significant boost, but given the economics behind streaming itself, it likely did not help him pay off over $2 million in back taxes.
How much did he allegedly owe? $750,000
What happened? The singer was hit with the massive tax lien at the top of October 2015 for unpaid taxes stemming from 2013 — and he allegedly paid the whole debt off in one check, before the month was out. Must be nice!
How much did he allegedly owe? $800,000
What happened? Anyone who’s seen his Behind the Music (remember those?) knows that Hammer blew through an astounding amount of money so quickly that he hit the skids in the late ’90s, filing for bankruptcy in 1996. Coincidentally (or not), in 2015, the IRS claimed that he owed the agency for taxes unpaid from that year as well as 1997.
How much did he allegedly owe? $1.7 million
What happened? DMX is no stranger to jail time, his latest stint resulting in a guilty plea entered in court in December 2017 after being charged with not filing taxes between the years 2010 to 2015, a time period in which he allegedly earned over $2 million. In March of the following year, he was sentenced to a year in jail; before the sentencing, DMX reportedly asked the judge to play his song “Slippin’” in court, a request that, amazingly, was honored.