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2. Dolla Dolla Bills Y’all

Star of the show Will Smith wasn’t always the seemingly enlightened individual he is today. Before he became one of the richest celebrities around, his rap game earned him quite a few dollars as well. However, poor money management led to him owing the government $2.8 million, which he racked up by shirking income tax payments. Smith was in trouble and on the brink of bankruptcy after all his money and belongings were seized, but help was on the way. Quincy Jones, executive producer of the developing series, handpicked him to star in this new sitcom. The IRS then made Smith pay them 70 percent of his salary for the show’s first three seasons. Good thing it wasn’t canceled.

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