5 Best Guest Stars To Ever Appear On The Fresh Prince Of Bel-Air

We all loved The Fresh Prince of Bel-Air but who was your favorite guest to stop by the show? Well let’s run down a list of our favorite people to ever stop by for a guest appearance. Each of our favorites have different reasons why they’re on the list, take a look below.

1. Best Guest Star Overall: Don Cheadle

Appears In: Season 1 Episode  5, “Homeboy Sweet Homeboy”

Ok. Hear me out. I know there’s been other folks who’ve come through FP and killed it. But while some, like Tyra Banks, Nia Long, Jaleel White, and Donald Trump, have played themselves or characters like themselves, only one showed their range as an actor early on and became the focal point of an entire episode. Fresh off a turn in the film Colors (a movie often overshadowed by its far superior and less white-gazey cousin Boyz N The Hood) Don Cheadle guest starred as Will’s Philly homeboy Ice Tray, presenting a more wild, uninhibited version of Will to the Banks. He stole, he mocked Will’s study skills, and even pressed up on Hillary, much to the horror of Uncle Phil and Aunt Vivian. What makes Cheadle’s role so remarkable is the fact that we know him as a serious actor- this was a couple years from Mo Better Blues and over a decade away from his Oscar-nominated turn in Hotel Rwanda. Comedy is hard to pull off for any actor who isn’t used to stand up, and Cheadle does it masterfully.  

2. Best Musical Guest Star: Queen Latifah

Appears in: Season 1, Episode 25  “Working It Out,” Season 2 Episode 8 “She Ain’t Heavy”

Thanks to Will Smith’s status in the music industry and EP Quincy Jones’ Quincy Jonesnes, music stars came all through FP. Some played themselves (Like the strangely rarely reran two part episode of the Fresh Prince where Will and Carlton compete for dates at the mall that had Al B Sure and Heavy D) and some played other characters. Queen Latifah lands at #2 because not only did she slay her role as a bossy starlet in the season 1 episode (and how clean is it that show-runners cast a Black plus sized female rapper to be the sought after starlet who bossed Hillary around?), she also played Will’s friend/crush in Season 2, becoming one of the earliest examples of body positivity in sitcoms. Her mastery of these quest star roles, I’m sure, had something to do with her snagging her own starring role on her Fox sitcom Living Single in 1993 and future Oscar-nominated, production company running, box-office breaking superstardom? 

3. Best OG Guest Star: Sherman Hemsley

Appears in: Season 3 Episode 7, “Here Comes the Judge”

One of the cool things about sitcoms is the joy of seeing OG’s slide through the following decade’s shows with the same energy they had in their heyday. This was the case for John Amos, Richard Roundtree, and The Jeffersons’ Sherman Hemsley, who played Uncle Phil’s boorish nemesis Judge Carl Robertson. It’s rare that you see someone as obnoxious as Will, but fun to see a true villain on the show. 

4. Best Comedian Guest Star: Chris Rock

Appears in: Season 6 Episode 2, “Get A Job”

Comedians of the early-mid 90s were a common feature on network TV, but since competition and projects (remember, FP was on at the same time as Martin, In Living Color, Living Single, A Different World, etc.) were plentiful in that time period few stopped by the fresh prince set to flex their comedic skills. Thankfully the Bel Air mansion got a visit from a pre Bring the Pain Chris Rock, playing a dual role as Maurice, a VIP guest on Hillary’s show. He also dons a dress (to some, this means becoming a government agent of the plot to feminize black men for financial gain) to play Jasmine, the homely girl Will volunteers to hit the town with. Misogynoir  aside, few comedians could share the screen with a season 6 me-me-me version of Will Smith and watching Will Smith almost break character dozens of times throughout the episode makes this special. 

5. Best Guest Star Girlfriend: Vivica Fox

Appears in: Season 1 Episode 19, “It Had to Be You”

Will’s girlfriends throughout the fresh prince deserve their own case study. Of the sexy #blackgirlmagic that strutted through Uncle Phil’s Foyer A young Vivica Fox was the most hilarious of the bunch as the demeaning Jasmine, sister of Jazz and pain in Will’s ass. It’s cool seeing a woman being bratty, sexy, and unapologetic at the same time and Vivica Fox debuted her signature swag that would follow her your whole career. 

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