By Megan Riedlinger
4:42pm PDT, Sep 25, 2023
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Will Smith got a squeeze from fellow '90s idol Enrique Iglesias while attending the Wango Tango concert in Los Angeles back in June 1999.
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Would you wear this to the Primetime Emmys? That's exactly what Will Smith did back in 1990 when he showed up in a tracksuit — sans shirt! — and sneakers. Yikes!
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Here's a fun '00s throwback! Check out Will Smith posing alongside Destiny's Child at the MTV Video Music Awards in New York City back in September 2001.
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Will Smith flashed a smile for a portrait in 1997 — the same year he starred in the blockbuster smash hit "Men In Black."
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Looking snazzy! Will Smith arrived in a sharp white suit, complete with a top hat, for the U.K. premiere of his flick "Wild Wild West" in 1999.
Second wife Jada Pinkett Smith, whom he married two years prior, was by his side for the big event.
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Will Smith rocked an eye-catching look at the American Music Awards in Los Angeles back in January 1991. Neon yellow is really his color!
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Will Smith picked up his fourth Grammy Award in 1999. That year, he won for best rap solo performance for his hit "Gettin' Jiggy Wit It" while wearing a gold and black leather suit.
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Look at these legends! Before his days on "The Fresh Prince of Bel-Air," Will Smith was known for his music. He's seen here attending an event for Los Angeles's KIIS FM radio station alongside Mariah Carey in September 1988.
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In 1990, Will Smith scored his acting big break as the titular character on the NBC sitcom "The Fresh Prince Of Bel-Air." He's seen here posing for a promotional photo while rocking his signature cool style.
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Will Smith and future wife Jada Pinkett made one of their first public appearances together at the premiere of "Devil In a Blue Dress" in Los Angeles in September 1995. That same year, Will divorced his first wife, Sheree Zampino. Will and Jada went on to marry in 1997.
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Who better to usher us into a new millenium than Will Smith and Jennifer Lopez?! Both had reached A-list status by this point. They flashed big smiles together at the Nickelodeon Kids' Choice Awards in April 2000.
