Will Smith Shares His Surprising Two-Year Tax ‘Break’ Following His Grammy Triumph.

Will Smith. Gerald Matzka/Getty Images

Will Smith reflects on his journey to stardom and the challenges he faced along the way.

Before his iconic role in The Fresh Prince of Bel-Air and a successful film career, Smith, now 55, was half of the rap duo DJ Jazzy Jeff & the Fresh Prince. In 1989, they won the first Grammy for Best Rap Performance with their song “Parents Just Don’t Understand.”

However, despite his growing fame, Smith encountered financial difficulties in the late 1980s. He revealed on the “7PM in Brooklyn with Carmelo Anthony and Kid Mero” podcast that he had neglected to pay his taxes, leading to a sobering realization.

“I think it was ’88. We had won a Grammy, but I had neglected to pay my taxes,” Smith shared, recalling how the Internal Revenue Service (IRS) deemed he owed nearly $3 million in taxes. “I was [thinking] the IRS gets money from everybody; they don’t need mine. But they felt differently… So I was a little down and I went out to LA. I sold everything in Philly. I was broke, completely broke.”

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

Smith eventually signed a deal with NBC to star in The Fresh Prince in 1990, turning his fortunes around. However, he recalled a pivotal moment in Los Angeles that served as a turning point.

Smith recounted visiting a club and spotting members of the group E.U., who had supported him and Jazzy Jeff on tour. As E.U. was enjoying success with their hit song “Da Butt,” Smith realized their contrasting fortunes. He recalled being unrecognized by the club’s security and the moment he decided to turn his career around.

“We started to fall off as they were rising,” Smith explained. “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 ****ing star on earth.”

Smith’s determination and talent led to a successful career, and his latest movie, Bad Boys: Ride or Die, hit theaters on June 7, showcasing his enduring popularity.

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