Current age: 45
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 beat box. 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 Smith 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."