The Fresh Prince Of Bel-Air broadcast its 148th and final episode on May 20, 1996. At that time, Will Smith was 27 years old and progressing into film for what has proven to be an incredible entertainment career. The MC-turned-actor from West Philadelphia, Pennsylvania had won two Grammy Awards. He would soon double that tally, and garner two Academy Award nominations.

By way of the show, executive produced by Quincy Jones, Will Smith’s character delivered aspects Hip-Hop culture to the living-rooms of the mainstream world. As a lovable and mischievous protagonist of the same name, The Fresh Prince spread parts of the culture’s lexicon. Heavy D, Queen Latifah, and Doctor Dré were among the guest stars. Beyond Hip-Hop, the show had heart and soul. Even more so than the “Huxtable” family, the “Banks” represented an upper-class Black family, with a mansion, pool house, club memberships, Mercedes Benz sedans, and a wise-cracking butler. In a way, the show was The Cosby Show-meets-Mr. Belvedere-meets-Silver Spoons, and yet completely its own thing. Memorable episodes addressed racial profiling by police, absentee fathers, and gun robberies. The laugh-track seemingly never stopped, but the series (reportedly considered for Juice Crew’s MC Shan), did so much more than just entertain.

The Original “Aunt Viv” Responds To The Fresh Prince Reunion Photo & It’s Too Hot For TV

Upon the September 10, 1990, debut of The Fresh Prince Of Bel-Air, Will Smith’s musical partner was also involved. Together, they created one of the most iconic themes and show openings of all time. DJ Jazzy Jeff & The Fresh Prince had released three Jive Records albums. The group’s most recent, And In This Corner… had already been gold-certified less than three months after release—nine months before the series debut. The DJ/producer who sought out The Fresh Prince as the MC to his musical group back in Philly took on the character of “Jazz.” Jeffrey Townes, the charismatic and quiet-cool champion turntablist played a caricatured part. With his shades on, “Jazz” represented Will’s sidekick from the wrong side of the tracks (read: Compton) who said the wrong things, and could not refrain from advances to Karyn Parsons’ “Hilary Banks” character.

As recently as this week, there are frequent speculations of a Fresh Prince Of Bel-Air reboot. The beloved original remains in syndication. While in Poland for Red Bull 3Style World Finals, HipHopDX‘s Jake Rohn asked Jazzy Jeff his thoughts on who in Hip-Hop, could fill Will Smith’s high-top sneakers. “I think Chance [The Rapper] would be a really good ‘Fresh Prince,'” Jeff begins. Asked why, the A Touch Of Jazz founder elaborates, “‘Cause Chance seems to always have a lighthearted demeanor. He’s got a serious side to him, but Chance is always smiling. Chance is always trying to do something positive. I think Chance would be a really good ‘Fresh Prince.'”

Imagine The Fresh Prince With No “Hilary” or “Carlton.” It Almost Happened…

Asked if he saw some of Will Smith in the Chicago MC/singer, Jeff says yes. “Chance is a trailblazer; Will has always been a trailblazer. There has never been an ‘I can’t.’ I really think I got a lot of that from him that there’s no plan B. Plan B just means you think plan A can fail. ‘This is what I’m gonna do, and I just need to do it.’ There’s no ‘I hope it happens.’ No. It’s, ‘It might take a little time, but I’m just gonna go do it.’ I think for Chance, to be as young as he is, to remain independent, to understand [the music business], I think is great. Because it’s very easy to fall into those pitfalls. It’s very easy for someone to bring you a suitcase full of money and change your entire perspective, instead of realizing that [you] could probably have 10 suitcases of money if [you] just keep [ownership].”

Notably, Chance has been making forays into acting. The Grammy Award-winner played parts in two small films, Donald Glover’s Clapping For The Wrong Reasons and 2015’s Mr. Happy. He ascended from an SNL musical guest to a show host.

Did You Know The Carlton Dance Was Completely Improv? The Man Explains

Last year, DJ Jazzy Jeff & The Fresh Prince released and performed single “Get Lit.” Jeff also formally released an ensemble album (featuring members of The Roots, SiR, Vidal Harris, and others), Chasing Goosebumps, alongside singer Glenn Lewis.