Will Smith (2 Oscar Nominations)

From small-time Philadelphia rapper to rising TV star, and finally a pop culture icon thanks to hit blockbusters, Will Smith’s talent and charisma weren’t questioned until he decided to try his hand at dramatic acting. He put those doubts aside when he landed his first Oscar nod for his portrayal of legendary boxer Muhammad Ali in Michael Mann’s 2002 biopic Ali. However, he would lose the distinction of being the first American-born African American Best Actor winner to Denzel Washington after his explosive role in Antoine Fuqua’s Training Day. Smith would garner his second nomination in 2007 for the drama The Pursuit of Happyness and once again he would lose out to another African-American actor, this time to Forest Whitaker for his role in The Last King of Scotland.