Beloved for his good looks, easygoing wit and effervescent charm both on and off screen, this hip-hop star turned actor has come a long way from his days rapping on the streets of Philly. Initially Smith came to prominence as the Fresh Prince, one half of the popular rap duo DJ Jazzy Jeff and the Fresh Prince, which released the catchy, PG-rated hits "Summertime" and "Parents Just Don't Understand," the latter winning the first-ever Grammy Award for Best Rap Performance in 1988. Still immature, Smith fell victim to the pitfalls of sudden success, squandering his money and teetering on the verge of bankruptcy, but TV soon changed his life and career. Beginning in 1990, Smith lent his considerable charisma to the sitcom The Fresh Prince of Bel-Air, in which he more or less played himself: a smart-alecky city kid who moves in with his stuffy, rich relatives. During his six years on the show, he launched a movie career, wisely playing roles antithetical to his small-screen persona (a gay con artist in Six Degrees of Separation, a quip-happy cop in the action comedy Bad Boys). By 1996, Smith was ready to focus on films full-time. Picking his projects carefully (and often supplying songs for the soundtracks), he appeared in one blockbuster per year — Independence Day, Men in Black, Enemy of the State — and although the films didn't highlight his versatility, they did prove his box-office appeal as the quintessential nice guy who could kick ass if needed. That nice-guy reputation extended to his personal life as well. Despite his mounting fame, Smith was never in the tabloids. Even his ex-wife, Sheree Zampino, got along with him and his new spouse, Jada Pinkett Smith. (In the '00s, he and Pinkett Smith cocreated and produced the sitcom All of Us, loosely based on their own experiences as a blended family.) Although Smith was a veritable A-list star — one of the few African-American entertainers who was bankable with audiences of all races — he still longed to be taken seriously as an actor. So in the '00s, he headlined two prestige projects back-to-back: the misguided The Legend of Bagger Vance and the 2001 Muhammad Ali biopic Ali, a performance that earned Smith solid reviews and his first Oscar nod, even though the film itself was a flop. Unsurprisingly, he then returned to his comfort zone, appearing in the sequels to two of his earlier hits (Men in Black II and Bad Boys II) and even began producing his own vehicles, including the poorly reviewed 2005 romantic smash Hitch, which proved that perhaps critics — not parents — were the ones who just didn't understand. The next year, he earned Oscar, Golden Globe and SAG nominations playing father to his real-life son, Jaden, in the inspirational drama The Pursuit of Happyness.