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Top 10 Rappers Tax EVA- to the SION

Yo! Word! These are just a few of the slogans thrown at you when you pay a visit to TurboTax's The Tax Rap website. Intuit are trying to kick the flava and drop the mad knowledge to da kidz that "nothing goes better together than Rappin' and Taxes!"

So how do you get down with the prospect of doing your taxes? You hire Vanilla Ice as your shill, and ask all the random idiots who visit your site to submit their rap to their YouTube channel. It's a genius idea and it beggars belief – yo!

Now I may be a crusty old breakdancer who has trouble differentiating between what's hip and what's not nowadays, but I'm pretty sure that Vanilla Ice has never been relevant when it comes to rap music. Aren't Hip-Hoppers all about being thugged-out gangsters who wouldn't think twice about pimping out their grandmothers? Do you really believe Biggie Smalls would rather sit down to fill out his 1040 than bust a cap in some beyatch’s ass?

I don’t really have the grill to answer those questions, but here's a list of some of the top 10 hip-hop tax flops:

1. Mystikal – The New Orleans rapper is currently serving a six-year sentence for sexual battery. In 2006, Mystikal pleaded guilty to not paying $271,000 in federal taxes for 1998/99. He received a one-year sentence. "Shake ya ass, but watch ya self" has now become a cautionary tale of what goes on in prison showers. Who said rappers don't make great role models?

2. Sir Mix-A-Lot – Baby got Back Taxes? You may already know this, but Mr. A-Lot is quite partial to the female derrière. Well, he also bragged so much about how much money he had that the IRS decided to audit his ass. As a result, they froze his accounts and put a lien on his house. He then immortalized his experience on the track "Take My Stash", which no one ever heard…but that’s just because they just wanted to hear the “big butt song” again. 

3. Suge Knight – Poor Suge has had rough life. The one-time gang-banger has visited the slammer a few times. Back in 2002, he was slapped with an IRS bill to the tune of $6 million. The big scary man behind Death Row Records seems real mad. Maybe it’s because his real name is Marion. Marion is a girl's name!

4. Jam Master Jay – The death of the man behind the wheels of steel for Run DMC came as a shock to most. Ever since his death, it seemed that JMJ may have been involved in some nefarious dealings. One thing's for sure, Jason Mizell was in deep financial trouble and owed a whole lot of money to “the man” - including penalties and interest, which could equal close to $500,000.

5. Lil Kim – The raunchy rapstress could probably suck the chrome off a donkey, but when April rolls around she forgets how much all that jewelry is worth. Kim got convicted on three felony counts: fraud, tax evasion and conspiracy.  She owed the IRS almost $1 million in back taxes and tried to blame it on her accountant, the shooting of her mentor Notorious B.I.G, and the 9/11 attacks and probably the North Atlantic cod wars. BOO HOO!

6. Jermaine Dupri  - This weasel-faced wizard behind the desk is the youngest charting producer in the history of music. Also he's the responsible for the sub-genre known as Kiddie Rap, which vaulted such pre-pubescent hoodlums as Kriss Kross and Lil Bow Wow to the top of the charts. Back in 2002, Dupri got raided by federal agents. They confiscated furniture, computers and cars. His debt to the IRS was reported as $2,541,865.

7. Irv and Chris Gotti - Rap moguls Irv and Chris Gotti surrendered to the authorities after being indicted on charges of laundering more than $1 million in drug proceeds through their record label, the Inc. (formerly Murder Inc.). Turns out the case was a bit flimsy, and the Murder Inc. brothers got acquitted, but I needed some padding on the list.

8. Master P – The feds made P say “UUUUUH!” when he failed to file a corporate tax returns for the $2.3 million his record label made in its first business year. The company kept no records of its business expenses or income. If only someone had kept no record of his professional basketball career.

9. Benzino –  Famous for his blatant self promotion in The Source magazine, my man was charged with failing to report $1.5 million income from 1999 to 2000. However a panel of jurors found him not guilty on two counts of failure to file tax returns.

10. Jay-Z – Damn! I can't find any dirt on him. He runs Roca-A-Fella tighter than a gnat’s chuff.

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