9 People Who Make Tax Evasion Look Sexy


It’s April 15 and your taxes are due (again), which means a few things: first, you’ll have less money than before. On the other hand, you might get a refund from the Federal government and end up with more money, then realize it was actually yours to begin with and it’s just now being returned. (You’ll probably blow it on Jordans and Powerball tickets anyway). Third, you’ve been doing lots of math even though you suck at it: deductions, exemptions, W-2s, W-4s, 1099s, 1044s, and all other kinds of numerical ridiculousness no decent person should have to go through. And fourth, you feel less sexy than usual.

You might think the answer to your sexiness problem is that new pair of heels, Weight Watchers, or a trip to Supercuts, but sadly you’re wrong: the answer is tax evasion. Sure, you’ll get in trouble with the law, but nothing boosts your short-term sex appeal like rebelliously shirking your tax obligations and blowing the extra cash on awesome shit like mansions, perms, and plastic surgery.

Just ask this group of sexies:

1. Al Capone

Photo Credit: New York Post

Tax evasion landed him in jail, but look at the bright side: he didn’t get prosecuted for murder, extortion, or any of the other vile shit he was into, and he basically ruled the city of Chicago for the entire Prohibition era. If that’s not sexy, I don’t know what is.

2. Lauryn Hill

Photo Credit: Bond

Recently plead guilty to tax evasion charges on a millie+ earned between 2005 and 2007, but homegirl can sing, rap, and pop out Marley babies with incredible skill and consistency: S-E-X-Y.

3. Ronald Isley (of The Isley Brothers)

Photo Credit: Centric TV

His smooth, silky hair and smooth, silky voice didn’t save him from serving three years in prison for $3 million owed to the IRS. But one could argue they made it worthwhile (especially the hair).

4. Lil’ Kim

Photo Credit: Billboard

The rap superstar (and former H&R Block employee!) was charged with owing almost $1 million in back taxes in 2005, but rest assured the money was well spent: nothing says sexy like a brand new nose (just ask Michael Jackson, R.I.P.).

5. Chuck Berry

Photo Credit: Maxwell Demon

The original rock superstar was sentenced to four months in prison because he owed the IRS $200,000 in 1979. But let’s face it, keeping that ‘do right had to be expensive! Stay sexy, Chuck.

6. Toni Braxton

Photo Credit: Search Weight

Looks like it’ll be awhile before Toni Braxton can actually “breathe again”: the R&B icon has filed for bankruptcy twice because she owes money to the IRS. Someone should tell her the only thing sexier than tax evasion is a high-speed car chase, and maybe her best move is to “hit the freeway” and move to Mexico.

7. Wesley Snipes

Photo Credit: Wikimedia

Finally, I can retire my “Free Wes” signs and stop picketing outside the jail building, because Nino Brown is home! Snipes served three years in a Pennsylvania prison for failing to file tax returns, but let’s hope that didn’t cramp his sexy too much.

8. Mary J. Blige

Photo Credit: Rhymes with Snitch

Apparently, Mary owes nearly a million in tax money to the state of New York. The fact that she hasn’t paid it yet might make her the sexiest person on this list.

9. James Brown

Photo Credit: All About Jazz

In the late 1960s, the Godfather of Soul owed over $6 million to the IRS, which it recovered by snatching many of his properties and holdings. At least he got to keep that perm (which is probably where all the money went anyway)!