IRS Tax Problems : 10 Celebrities Jailed on Tax Evasion Charges

IRS tax problems have sent many celebrities behind bars. With the recent guilty plea by DMX for tax fraud, in the amount of $1.7 million over a period of 5 years, has once again sparked a controversy over celebrities evading tax. With this, here are our top 10 tax troubled celebrities who had to face jail time for tax evasion/fraud.

Video : IRS Tax Problems List 

The Tax Problems List of Celebrities

  1. Lauryn Hill
    1. Famous for
      1. 8 time Grammy winner
      2. Former Fugees singer
    2. Tax evaded: Failed to pay taxes on more than $1.5 million revenue between 2005 to ’07
    3. Sentence: Sentenced to 3 months in the federal penitentiary
    4. Fun Fact:
      1. She claimed she stopped paying taxes after she dropped out of the music business
      2. She staged a post-prison show in 2013 after being released
  2. Ja Rule -Rapper and actor Ja Rule, whose real name is Jeffrey Atkins, got more than two years jail sentence for failing to file income tax returns between 2004 and 2006.
  3. Richard Pryor
    1. Famous for
      1. Regarded as one of the most influential comedians of all time
      2. Labeled “The Picasso of comedy” by Jerry Seinfeld
    2. Tax evaded:
    3. Sentence: 10 days behind bars in 1974
    4. Fun Fact: He told the Judge, “You know, I forgot” during his tax evasion trial
  4. Leona Helmsley
    1. Famous for
      1. Billionaire hotel tycoon, whose elitist persona earned her the nickname “the queen of mean”
      2. Famous for saying “Only little people pay taxes”
    2. Tax evaded: $1.2 million in 1988
    3. Sentence:
      1. Sentenced to 4 years in prison, and 750 house of community service
      2. However, she ultimately served only 21 months in prison
    4. Fun Fact:
      1. The judge overseeing her community service sentenced her to an additional 150 hours after learning that she made her employees do some of her chores
  5. Fat Joe
    1. Famous for
      1. Famous Rapper
    2. Tax evaded: $3 million tax evasion
    3. Sentence: Four months in federal prison and a $15,000 fine
    4. Fun Fact:
      1. Real name is “Joseph Antonio Cartagena”
  6. Chuck Berry
    1. Famous for
      1. Rock and roll pioneer
      2. Popularly known for his song “Roll over Beethoven.”
    2. Tax evaded: $200,000 of unpaid taxes
    3. Sentence: 4 months in prison & 1,000 hours of community service
    4. Fun Fact:
      1. He started his sentence right after playing for Jimmy Carter at the White House
      2. He completed his community service quota by doing benefit concerts
  7. Darryl Strawberry
    1. Famous for
      1. Basketball wizard
      2. Domestic abuse and repeated abuse of drugs
    2. Tax evaded: Failed to report more than $350,000 from 1986 to 1990
    3. Sentence: 3 months in prison, and three month home confinement
    4. Fun Fact:
      1. He was dropped by the San Francisco Giants for persistent drug abuse (Cocaine)
      2. He was indicted for three counts of tax evasion but plead guilty to only 1, thus bringing down his maximum sentence down from 15 years
  8. Heidi Fleiss
    1. Famous for
      1. Known as the “Hollywood Madam”, she was famous for running in an elite prostituting ring
    2. Tax evaded:
    3. Sentence: 37 months in prison
    4. Fun Fact:
      1. Her tax evasion sentence ran concurrently with her money laundering count & 8 counts of
      2. She was given a far lesser sentence than the maximum prison sentence due to expert testimony that money laundering laws had been drafted with mobsters in mind, and the judge weighing in by saying that male customers of prostitution are usually not tried
  9. Pete Rose
    1. Famous for
      1. Major League Basketball player & manager
    2. Tax evaded: Tax fraud
    3. Sentence: 5 months in prison in 1990, and $150,000 in tax liens
    4. Fun Fact:
      1. After getting banned from lifetime from Baseball by Baseball commissioner Rob Manfred in 2015, he said, “I should actually be the commissioner of baseball.”
  10. Wesley Snipes
    1. Famous for
      1. Actor, film-producer, Author
      2. Founder of Amen-Ra Films
      3. Played the role of “Blade” in the blade trilogy
    2. Tax evaded: $7 million during 1999 through 2001
    3. Sentence: Previously served a 3-year sentence
    4. Fun Fact:
      1. He served three years, the maximum punishment for three counts of misdemeanours for failing to file tax return, in McKean Federal Correctional Institute
      2. He was recently engaged with the IRS in a court battle over his civil taxes, where the IRS served him with a $17.5 million tax bill
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