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Will Smith

Current age: 46

Career at 20: Will formed a hip-hop duo called DJ Jazzy Jeff & The Fresh Prince with his childhood friend Jeffrey Townes. Clarence Holmes, or Ready Rock C, was also a member and was referred to as the human beatbox. The duo stormed the rap scene with parent-friendly tunes and even won the first Grammy awarded in the rap category in 1998.

Relationship status at 20: Will was reportedly single.

Quoted at 20: During a radio interview, Will explained how he got into business with Townes: "Jeff had this stuff: canned fart spray. And we were spraying it in to the fan and watching people run out of the party. We were a crew ever since then."

Image Source: Getty / Barry King
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