Will Smith
Fresh from his Grammy-winning rap career, Will Smith became the biggest movie star of the '90s—charismatic, relatable, and seemingly incapable of releasing a film that didn't top the summer box office. By 1999 he was untouchable.
Will Smith's 1990s trajectory was a masterclass in ascension. The decade began with The Fresh Prince of Bel-Air (September 1990), a sitcom that translated his charm and comedic timing from music into television, making him a household name. He was already a Grammy-winning rapper—"Parents Just Don't Understand" was a classic, and the Fresh Prince's 1989 Grammy (the first-ever for rap) proved the medium's cultural credibility; 1991's "Summertime" added another mid-show.
In the mid-90s, Smith made the leap to film: Bad Boys (1995) with Martin Lawrence, then back-to-back Fourth of July blockbusters — Independence Day (1996) and Men in Black (1997) — each one the event movie of its summer. His 1997 album Big Willie Style produced the crossover hit "Gettin' Jiggy wit It," cementing him as a multi-platform star. By 1999, Will Smith was the biggest movie star on the planet; even Wild Wild West (1999), widely panned, couldn't dent his cultural dominance or bankability.
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The Fresh Prince of Bel-Air
NBC's six-season hit brought hip-hop culture to mainstream network TV, launching Will Smith from music-industry crisis to acting stardom. A sitcom pitched by music manager Benny Medina about his own rags-to-riches story, it gave the world one of the most recited theme songs ever — and Alfonso Ribeiro's Carlton Dance defined a generation's pop-culture moves.
Michael Jordan
The Bulls dynasty alpha who made basketball bigger than basketball itself. Six NBA championships in two three-peats, a Gatorade slogan that became a religion, a baseball detour ended by a two-word press release, and Air Jordans that outlasted his career by decades.
Big Willie Style (Will Smith)
The Fresh Prince goes solo — and takes over the planet. 'Gettin' Jiggy Wit It,' 'Miami,' 'Just the Two of Us': radio-owning, profanity-free hip-hop from the guy who was simultaneously the biggest movie star alive. Nineteen ninety-eight belonged to Will.
Independence Day
The White House explodes. Will Smith punches an alien and delivers the one-liner. Jeff Goldblum uploads a virus from a PowerBook. The movie that made July 4th weekend a permanent blockbuster holiday — and the biggest film of 1996 by a mile.