Will Smith Recalls Not Paying His Taxes for 2 Years After Grammy Win

Will Smith.
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Will Smith is looking back at how far he’s come.

Before The Fresh Prince of Bel-Air and a glittering movie career, Smith, 55, was one half of the rap duo DJ Jazzy Jeff & the Fresh Prince, with whom he won the first-ever Grammy for Best Rap Performance 1989 with the song “Parents Just Don’t Understand.”

Despite his fame and success, Smith experienced financial troubles in the late 1980s into 1990 after the Internal Revenue Service (IRS) deemed he had failed to pay nearly $3 million in taxes.

“I think it was ‘88 and we had won a Grammy, but I had neglected to pay my taxes,” Smith recalled the sobering time in his career on the Thursday, June 6, episode of the “7PM in Brooklyn with Carmelo Anthony and Kid Mero” podcast.

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‘I was [thinking] the IRS gets money from everybody, they don’t need mine — but they felt differently,” he continued. “So I didn’t pay taxes for the two years — and winning a Grammy and all that — so they just thought they should take my stuff. So I was a little down and I went out to LA. I sold everything in Philly. I was broke, broke.”

DJ Jazzy Jeff & The Fresh Prince

DJ Jazzy Jeff & The Fresh Prince.
Michael Ochs Archives/Getty Images

Eventually, Smith landed on his feet by signing a deal with NBC to star in his own sitcom — The Fresh Prince — in 1990.

But when he first moved out to Los Angeles from Philadelphia, Smith recalled one moment he knew he had to turn things around because his star was beginning to fade.

Smith said he went to a club where he spotted members of the group E.U., who had supported him and Jazzy Jeff on tour and were enjoying success with their hit song, “Da Butt.”

“We started to fall off as they were rising,” Smith explained.

“The security didn’t recognize us,” he said of queuing to get into the club. “I looked in and I saw one of the members of the group. I was like, ‘Yo, yo, get the security,’ and he flagged me off and the door closed in my face. I turned to Charlie [Mack, his childhood friend and security guard] and I said, ‘That will never happen again.’ I just made a decision in that moment: I was going to be the biggest f–king star on earth.”

Smith’s latest movie, Bad Boys: Ride or Die, is in theaters on Friday, June 7.

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