If you think the rich and famous don’t have to worry about taxes, think again. The taxman waits for no one, not even celebrities, as these hot shots learned the hard way.
Chuck Berry: Failing to file tax returns
One of the original rock and roll superstars, Chuck Berry, has enjoyed fame and fortune since the mid-50s. Labeled a chronic tax evader by the IRS, he served a 120-day sentence in 1979 for not paying his taxes. This music icon was no stranger to jail, though, having served three years for armed robbery while still in high school and another three years in 1962 for transporting a 14-year-old girl across state lines.
Wesley Snipes: Owning over 5 years in back taxes
A highly recognizable Hollywood actor, Wesley Snipes has acted in 58 films since the mid-80s, earning himself a star on the famous Hollywood Walk of Fame in 1998. In 2008, Snipes was sentenced to three years in prison for allegedly not filing his income tax returns for 1999 through 2004. He denied any wrongdoing, blaming his accountant and lawyer for failing to properly report his income or file tax returns. The government saw through the ruse, and Snipes was ordered to pay over $5 million in fees. On top of these charges, there were also charges of conspiracy to defraud the government.
Strangely enough, part of his defense on the conspiracy charges was that he was a non-resident alien of the United States despite being born in Florida. Snipes apparently tried to claim a multi-million dollar refund on his income taxes on the basis that non-Citizens don’t have to pay taxes in the United States.
Martha Stewart: Not paying property taxes
The queen of all things home famously missed out on a few years in her own house after spending five months in federal prison for convictions surrounding insider stock trading. But less famously, Martha Stewart was also charged by the IRS for tax evasion. She had to pay nearly a quarter-million in back taxes and penalty fees for failing to pay her property taxes in New York. Martha Stewart tried to craft and cook up an excuse, saying she didn’t think she had to pay the taxes since she didn’t live at the property full time.
Nicolas Cage: Paying incomplete returns
A long-time member of Hollywood royalty, Nicolas Cage has acted in 77 films since the early 80s. He won an Oscar for his role in Leaving Las Vegas and was nominated for or awarded a total of 45 other acting awards during his career. No surprise then that he’s paid over $70 million in taxes over that period. It is surprising that he failed to report all of his income and did not pay $14 million in back taxes to the IRS. In 2009, he was issued a lien by the IRS for delinquent taxes, charged interest and penalties, and issued a separate lien for an unpaid property tax bill.
Mike “The Situation” Sorrentino: A “Shore” federal crime
Known for his outlandish behavior on the MTV series Jersey Shore, Mike Sorrentino also practiced some inappropriate tax behavior. With earnings over $9 million from 2010-2012, he falsely filed tax returns to reduce his tax charges. The IRS charged and convicted Sorrentino of tax evasion and sentenced him to eight months in federal prison in 2019, followed by two years of supervised release. While he spent his time behind bars working on as much of his GTL (gym – tanning – laundry) habits as he could, let’s hope he also hired someone to correctly file tax returns for him moving forward.
Ja Rule: Adding tax evasion to existing crimes
Popular rapper and musical artist Ja Rule was singing a different tune when the IRS called him out for failing to file or pay tax returns from 2004-2008. With no good reason for the error, Ja Rule pleaded guilty. He agreed to pay more than $1.1. million in back taxes as well as fees and penalties assessed by the IRS and the Federal government. The singer was sentenced to 28 months in prison for tax fraud in a New York federal facility in addition to a two-year prison sentence he was already serving on weapons charges.
Al Capone: Crime boss taken down by the IRS
One of the most notorious and original gangsters, before gangsters were known for record albums, Al Capone was Alcatraz’s most famous inmate. Although his criminal activities as a mafia boss were well known, tax evasion ultimately put him behind bars in 1931. Despite his brutal actions as a mob boss, he had his fans who cheered when he showed up at baseball games in Chicago. He loved the attention, but his popularity was a huge factor in his conviction. The courts wanted to make an example of him and doled out the longest sentence to date for someone convicted of tax evasion: 11 years in Federal prison.
Richard Hatch: Surviving an IRS audit
In 2000, Richard Hatch gained fame and notoriety as the first-ever winner of Survivor. He was known as a supervillain on the show, so it didn’t surprise many when he was subsequently charged with tax evasion in 2003 for allegedly not paying income taxes on his $1 million Survivor winnings. Despite serving 51 months for the crime and further tax-evading allegations on a Sydney, Nova Scotia property in 2013, he still maintains his innocence. He claims that he was just late in filing his 2000 and 2001 taxes, and the tax on the $1 million was somehow overlooked by the IRS and uncovered during an audit.
Willie Nelson: Singing your way to solvency
If the IRS comes calling for millions in back taxes, you might be tempted to wallow in a sad country tune. Imagine how Willie Nelson felt when the IRS uncovered his failure to file taxes and sent him a bill for $16.7 million. Not to be daunted by his tax troubles, he sold many of his collectibles and assets to cover as much of the tax debt as possible. As funds ran out, he turned to what he knew best: music. Willie Nelson released a new album titled “The IRS Tapes: Who Will Buy My Memories” to capitalize on fan support for his plight. Proceeds helped to pay off his tax debt as well as promote the sale of his belongings. Remarkably, many devoted fans actually returned items to Nelson after making the purchases to help his tax debt.
Richard Pryor: Forgetting isn’t funny
Although Richard Pryor is renowned as a comedian, mostly in the 70s and 80s, he is also known for his widely publicized, troubled private life. His seven marriages, battles with drugs and alcohol, and failed suicide attempts on a movie set in 1980 all contributed to his Hollywood notoriety. Considering the magnitude of his other troubles, it’s no surprise that his 10-day stint in prison after being convicted of tax evasion in 1974 received little attention. Always the funny man, his defense included the statement: “I forgot.” Not quite a good reason for failing to pay your tax bill.
Sophia Loren: Cleared from fraud accusations
The world-renowned Italian actress and sex symbol Sophia Loren has lived in Switzerland since 2006. Maybe that’s partly because the Italian government sentenced her to 17 days of jail time in 1982 for allegedly filing a fraudulent tax return in 1974. After decades of denying and appealing the case, she was finally vindicated in 2013 when the Italian Court of Cassation ruled that her 1974 tax returns were correct after all.
Judy Garland: Owing $4 million in back taxes
Best known for her role in The Wizard of Oz when she was just 17 years old, Judy Garland is one of the most iconic Hollywood actresses of all time. Despite a successful career spanning four decades and many awards, including the Cecil B. DeMille Award for lifetime achievement in the motion picture industry, she struggled in her personal life. She married five times and battled with drug and alcohol addiction. Unfortunately, she was also plagued by tax and financial troubles. In the final years leading up to her death by accidental overdose in 1969, she lived in a series of hotels and rental houses after the IRS repossessed her home in 1964 for her failure to pay a $4 million tax bill.
Darryl Strawberry: New York star falls with fraud
One of the most lauded right fielders in baseball during the 1980s, Darryl Strawberry’s on-field success did not carry over to his personal life. The all-star player struck out with the IRS and a series of tax evasion cases. Darryl Strawberry was negligent in paying taxes and failing to report funds collected on the sale of merchandise and memorabilia he used as a significant revenue stream. Over time, it was discovered that he also owed back taxes from filings in 1989, 1990, 2003, and 2004. The baseball star was ordered to pay nearly $1 million in back taxes, interest, and fees to the Federal government. To recoup the rest of its losses, the IRS auctioned off additional assets and annuities from his time as a New York Met, amounting to over $1.2 million.
Lauryn Hill: Private life is no IRS escape
Known as the lead singer of the Fugees, Lauryn Hill gained fame as a singer after an early start as an actress in As the World Turns and Sister Act II. Her career hit its peak in 1999 when she won five Grammy Awards, having sold 8 million copies of her solo album the previous year. The pressures of fame got to her, and she dropped out of the public eye shortly afterward. Hill resurfaced in 2012 but not for her singing. She was sentenced to three months in prison for failing to pay the IRS nearly $1 million in back taxes.
Known as the “Hollywood Madam,” Heidi Fleiss was the original millionaire matchmaker, providing high-priced prostitutes to some of the richest men in Los Angeles. Although she never revealed the identities of her clients, they are rumored to have included Charlie Sheen. She was arrested in 1993 and sentenced to serve three years in jail, but her conviction was overturned on appeal in 1996 after jurors admitted to vote-trading and other no-nos. In 1997, she was arrested for tax evasion and sentenced to 37 months in federal prison.
Tax debt relief for celebrities and regular folk
If you’re struggling to pay back taxes, you are probably considering whether there are tax debt relief programs available. Celebrities, such as Nicolas Cage, have benefited from tax relief programs, such as installment agreements. You can also qualify for multiple tax relief options, such as penalty abatement, offers in compromise, and filing for currently-not-collectible status. Hiring a tax relief company with tax attorneys and enrolled agents on staff can help navigate these programs. Although it’s important to exercise caution and avoid scammers, there are legitimate tax relief companies that provide real value. The companies below are included in our list of the best tax relief companies currently available.