Smith's first claim to fame came in the music industry with his pal DJ Jazzy Jeff in the late 1980s with their hit "Parents Just Don't Understand." From there, the rapper found his talent in acting, landing perhaps his most iconic role to date as the Fresh Prince in "The Fresh Prince of Bel Air."

Smith made about $10 million thanks to his early years as a rapper, but as soon as Uncle Sam caught wind of Smith's earnings, the actor was in trouble. Smith spent all of his fortune before considering taxes, leading to the actor owing the IRS $2.8 million and leaving him bankrupt.

Smith's money troubles began just before he was cast as the "Fresh Prince," which meant the first few paychecks of his comedy series went straight to the IRS. In fact, according to "Will Smith: A Biography," for the first two years of the show, the IRS was taking 70% of every paycheck.

After blowing his millions from his music career, Smith spent the first few years as a series lead who still rode the bus. "Being famous and broke is a s*** combination," Smith said on the YouTube show "StoryTime," and he's also called himself "financially nervous" to this day.