Acclaimed actor and rap artist Will Smith has achieved a level of Hollywood fame rarely attained by a Black celebrity. Early in his career, Smith stated that he aspired to be the world's most famous movie star. By the time he was named the world's top film attraction in 2008, he had fulfilled his goal. While his rise to a place of worldwide prominence and cultural relevance has made him iconic, his accomplishments have not received the full and thorough acknowledgement and analysis they merit. This is the first full-length critical look at the significance of Will Smith's achievements over a more than 30-year career. Many of his films have broken cultural norms by depicting Black men in groundbreaking social settings, like the role of the world-saving hero in his most popular films. In addition to analyzing Smith's filmography, this work contextualizes other popular and common portrayals of Black men in media and society. Finally, this book examines Smith's work in his middle age, ruminating on his ability to adapt to the realities of a new Hollywood.