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Will Smith doesn’t have to worry about money anymore. Even if he stopped making movies today, he’d probably still collect comfortable residuals from movies like Independence Day, Men in Black and as recently as Aladdin. Not to mention The Fresh Prince of Bel-Air. However, early in his career, Smith got into some financial trouble, and not quite as early as you may think. 

Fresh Prince rapper Will Smith tells stories on stage
Will Smith | Lia Toby/Getty Images

Smith described his financial struggles in his autobiography, Will. However, this story comes after he’d already had success in music with DJ Jazzy Jeff and the Fresh Prince. 

How much did Will Smith owe for his DJ Jazzy Jeff and the Fresh Prince albums?

The story comes after the release of And In This Corner…, the third album from DJ Jazzy Jeff and the Fresh Prince in 1989. It wasn’t the hit He’s the DJ, I’m the Rapper was and it was before The Fresh Prince of Bel-Air, but Smith still had plenty of income to tax. 

“I didn’t pay my taxes,” he wrote. “It’s not like I forgot, it was more like… I just didn’t pay my taxes. In January 1990, Uncle Sam decided that I’d had enough fun and he wanted his.”

Smith didn’t specify the amount of his tax debt, but he did indicate the amount of income that could be taxed. 

“I owed the IRS taxes on around $3 million of income,” he wrote. “I think somewhere above a million dollars, Uncle Sam shifts from ornery to irritable and everything north of $2.3 million makes him aggressive and cantankerous.”

Will Smith needed help with his taxes

DJ Jazzy Jeff and the Fresh Prince started rapping when Smith was still in high school. He was still only 21 when the tax problems hit, so he went to his partner, James Lassiter, for advice. 

‘Y’all are stoopid as sh*t,’ JL said,” he wrote. “‘Y’all understand this is a big problem, right?”

Lassiter also gave way that Smith wasn’t the only one who didn’t pay his taxes. Jeff Townes, DJ Jazzy Jeff himself, was in the same boat.

“I didn’t notice in the moment but JL kept saying ‘y’all’ denoting a plural of stupidity,” he wrote. “I would later discover that Jeff hadn’t paid his taxes, either. And to make matters worse, JL had been lax on billing us for his commissions, so not only had we spent all of our money, we had spent JL’s cut, too.”

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Lassiter set both Smith and Townes up with financial planning for the rest of their careers.

“JL hired a tax attorney (for me and Jeff — he paid his taxes), scheduled a meeting, showed them the notices from the IRS,” he wrote. “He also engaged an accounting firm, Gelfand, Rennert & Feldman, to oversee our hypothetical future earnings.”

The Fresh Prince of downsizing 

Smith would make enough money in the future to pay past debts and get current on his tax obligation. However, prior to The Fresh Prince of Bel-Air, and with little income coming from And In This Corner…, Smith had to find money fast. That meant getting rid of all the bling he bought after DJ Jazzy Jeff and the Fresh Prince’s first hits.

“We were all broke,” he wrote. “First went all the cars. Then my motorcycles. Stereo systems are very expensive when they go in — they’re worth damn near nothing when they come out. Then the excruciating decision was made — IRS, attorney, and accountants unanimously agreed: I would have to sell the Lower Merion house, pool table included.”

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