Will Smith learned a tough financial lesson early on in his career.

During an episode of the podcast, “7PM in Brooklyn with Carmelo Anthony & Kid Mero,” Smith reflected on a peak moment in his career in 1988. Smith had won a Grammy for Best Rap Performance with DJ Jazzy Jeff for their single “Parents Just Don’t Understand,” Pop Sugar reports. Their win was even more significant because it was also the year that the Best Rap Performance category was introduced.

However, that career highlight also came during a time when Smith ran into trouble for neglecting to pay his taxes.

“I was like, you know the IRS gets money from everybody, they don’t like need mine, but they felt differently,” Will said on the podcast. “So, I didn’t pay taxes for the two years and won 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 L.A. I sold everything in [Philadelphia, PA], like I was, like, broke-broke sold everything in Philly.”
According to Complex, Smith’s financial troubles were the result of his spending habits, which included motorcycles, cars, and designer clothing following the release of the 1988 single.
His saving grace appeared when Benny Medina, who later became Jennifer Lopez’s manager, pitched him the idea for “The Fresh Prince of Bel-Air,” a show inspired by Medina’s own life, per the outlet. Smith was then encouraged to consider meeting with Quincy Jones, a producer on the show. In 1989, Smith wound up in Jones’ living room auditioning for the part with little time for preparation.
The rest is history as Smith starred as the lead character on “The Fresh Prince of Bel-Air” for its six-season run.