At 57 years old today, Will Smith is a multi-hyphenate with several Grammys and an Oscar under his belt. Smith may be a movie star now, but as many remember, he was once a burgeoning rap superstar. His prolific storytelling (and never dropping the F-bomb in his music), was only half of what set him apart from his industry peers in the hip-hop game.
Before The Fresh Prince of Bel-Air aired, Smith was known simply as the Fresh Prince. He dominated the R&B charts with his cheeky songs, which often felt like Saturday Night Live skits; for instance, his beloved hits “Brand New Funk” and “Girls Ain’t Nothing But Trouble.” In honor of Smith’s 57th birthday, here are five of his best songs.
Summertime
In 1991, Will Smith was still making hits with his R&B duo Jazzy Jeff & The Fresh Prince. Released at the height of The Fresh Prince of Bel-Air, the Grammy-winning song topped the Billboard Hot R&B Singles charts and peaked at #4 on Billboard’s Hot 100. The smooth and groovy single is peak ’90s R&B, and the perfect representation of summer.
Its slow tempo and catchy melody make it impossible to get out of your head, evoking serious ’90s nostalgia for driving around with the top down in a simpler world. 34 years after release, “Summertime” still holds up and deserves a spot on all the summer playlists for years to come.
Parents Just Don’t Understand
Another song from the hip-hop/R&B duo channels the teen angst that defined the ’80s and ’90s. While a lot of teenagers were funneling their rage through rock music, “Parents Just Don’t Understand” was the perfect sonic substitution for those not interested in hearing rock bands of the ’80s or the pop punk groups to come in the ’90s.
The tongue-in-cheek hit flawlessly represents Smith’s ability to mix comedy with music.TheFresh Princeof Bel-Air referenced the song several times during its run, and it also appeared in films and television shows like The Parent Trap (1998) and Jimmy Neutron: Boy Genius.
Among the comedic factors and Smith’s whiny impersonation of his mother, there is a lot of truth in the lyrics. From not being able to wear the clothes he wants, to stealing his parents’ Porsche in order to drive around with a girl, the song speaks to its audience of rebellious teens.
Miami
“Miami” is a single off Will Smith’s debut solo album, Big Willie Style. The funky, upbeat single leans on some disco and pop influences, sampling The Whispers’ “And The Beat Goes On.” It was the beginning of a new era for the rapper turned actor, proving wherever Willie went, he’d conquer.
“Miami” epitomizes the feeling of being young in the Magic City; it’s like being on college spring break all over again. The song spoke to the late 90s youth as Smith took home the Best Male Video award at the 1999 MTV Video Music Awards. Despite his refreshed music style, he maintained the sense of humor that made him so charming to begin with.
Switch
By 2005, Will Smith was firmly established as a movie star, but that didn’t mean his music career came to a halt. What did change was his audience. With his family increasingly in the public eye, Smith’s image evolved. Though he became a father back in 1992, it was his marriage to Jada Pinkett Smith—and the births of Jaden and Willow—that solidified his transformation into a full-blown family man.
“Switch” was released a year before he starred alongside his son in The Pursuit of Happyness. Needless to say, Smith’s life had drastically changed since his days of rapping about young women alongside DJ Jazzy Jeff. Smith showed up to the 2005 Kids’ Choice Awards with his wife and kids and performed “Switch” live on stage.
The not-so-child-friendly message of the song seemingly went over the kids’ heads as Smith introduced R&B to a new generation. While “Switch” may not be as critically acclaimed as his earlier Grammy-winning work, it’s still a classic Will Smith hit.
Gettin Jiggy Wit It
“Gettin’ Jiggy Wit It” is quintessential Will Smith. It’s fun, it’s light-hearted, and it makes even the most cynical music snob want to get up and dance. Smith could teach a masterclass on sampling, as the 1998 single borrows from Sister Sledge’s “He’s The Greatest Dancer,” The Bar-Kays’ “Sang and Dance,” and Whistle’s “Nothing Serious (Just Buggin’.)”
However, Smith brought enough of his own personal style to make the song feel as fresh as the self-proclaimed Fresh Prince himself. Whether it’s his best song or not is up for debate, but there’s no denying it’s the one Smith is typically associated with.
“Gettin’ Jiggy Wit It” won the Best Rap Solo Performance Grammy Award at the 1999 ceremony and spent three weeks at the top of the Billboard Hot 100 charts. There’s no denying the single helped cement Will Smith‘s legacy as a solo R&B artist.
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