The Best Cameos On The Fresh Prince

Written by Nick Santora 

In the land of television, the Fresh Prince is sneaker royalty. From his emergence on the national scene in his 1988 Parent’s Just Don’t Understand video, Big Willy proved he was ’bout that life, in his Porsche 930 Turbo, Le Coq Sportif tennis suit, and Vuarnet sunglasses. The good life wasn’t without struggle though, as we learned he asked his mom for adidas and she bought him Zips. This was a situation every kid could all relate to, and became a rallying call for everyone to protest back-to-school shopping at Sears, and elevate their game at the local tennis shop, for the finest in European sportswear.

By the time Will arrived in Bel Air, his fashion sense evolved with the times to revolve around the most current basketball sneakers, starting with the metallic Air Jordan V, mixed with a healthy dose of neon surf style. The first season was a continuous Nike commercial, featuring Air Jordans, Air Flights, and Air Trainer SCs, along with more obscure models like the Air Quantum Force and Air Ultra Force. Over the next few years, the styling continued to evolve with pop culture to get a little more rugged with overalls, Timberland boots, boots and those Spike Lee “Play Together” style Afro-centric prints. Whatever he wore, it always seemed authentic. If The Fresh Prince had a wardrobe stylist, they were a reflection of Will Smith’s personal style.

With the Fresh Prince’s musical pedigree and alignment with sneaker culture, came a connection with sports. This led to several athlete guest appearances on the show, over the years. Here is a list of all of them.

Riddick Bowe – “You Bet Your Life” – Season 3 / Episode 21

In the 1980 and 1990s, sit-coms would throw an occasional curve ball at you by dropping a heavy-duty episode that touched on a serious social issue that was relevant to the times. What’s Happening warned us of the dangers of joining a cult, and the legal repercussions of bootlegging a Doobie Brothers concert. Different Strokes had Arnold and Dudley smoking doobies in a bunk bed, and the best friends also found themselves in a quite precarious situation with a perverted photographer, with bad intentions. In this episode, entitled “You Bet Your Life,” the dangers of gambling addiction are addressed.

Will, Jazz, and Carlton hit the open road to visit a college, when they quickly find themselves being extorted by a backwoods mechanic at a remote highway rest stop, that just so happens to have a casino attached to it. Finding themselves strapped for cash and in a pickle, the boys decide to multiply their funds by gambling, in order to get their car back. This decision sends Carlton into a downward spiral, as he becomes cracked-out-of-his-mind on the adrenaline rush of the slot machine, and eventually resorts to begging for quarters when his money runs out. Will and Jazz leave their degenerate friend behind and hit the road, only to feel guilty about it and come back for him a few minutes later. Next thing you know, Riddick Bowe shows up at the casino in a sleeveless Canadian tuxedo, complete with cowboy hat and boots, and as Carlton steps away from his machine in search of another quarter, Bowe steps in and hits the jackpot. Missing out on that pull of the one-armed-bandit sends Carlton into a fit of rage directed at the heavyweight boxer. Will attempts to stick up for his friend, and after a brief plea for black unity, gets knocked out with one punch.

Evander Holyfield – “Deck The Halls” – Season 1 / Episode 15

After implying Ashley doesn’t know the meaning of Christmas, Will sets out on a mission to get her and the rest of the family into the Holiday spirit. The Fresh Prince takes it upon himself to bypass the snooty Beverly Hills decorating store recommended by Aunt Vivian, in favor of his own assortment of fake silver trees, colored garland, and plastic black Santas. Needless to say, the gaudy, over-the-top decorations outside the mansion don’t go over well with their uptight neighbors in Bel Air. During their family Christmas party, Will takes a phone call from an angry onlooker and starts running off at the mouth, and encouraging the caller to come over and handle the situation in-person. Jeffrey soon comes into the room to introduce the gentleman from the other end of the line, who’s now in the foyer, and ready to take him up on his offer. To Will’s surprise, reigning Heavyweight Champion, Evander Holyfield is his newest adversary, fresh off his title fight with Buster Douglas and rocking a crazy dope personalized BET network varsity jacket. Cooler heads prevailed and tensions were squashed when Evander recognizes Hillary from their high-falutin’ social circle and they exchange pleasantries and things are settled.

Isiah Thomas – “Courting Disaster” – Season 1 / Episode 11

Will and Jazz attend Carlton’s basketball practice for Bel Air Academy, where the team is filled with dweebs, but at least fitted in crispy Nike Air Flight 90s. Shortly into practice, the athletic director commits several student-athlete violations by introducing the coach to a big school booster who will donate large sums of money, only if the team can figure out a way to start winning. In a fairly racist move reminiscent of the movie Soul Man, the booster sees two black guys in the gym and asks why they aren’t on the team. In all fairness, Will is throwing down some serious dunks (for a high school walk-on) in a pair of all-red Nike Quantum Force hi tops that are hard as hell and warrant the first pick in any 1990 basketball draft. After some minor coercion from the coach, Will is joins the team and quickly becomes a star, much to the chagrin of jealous Carlton. During an X’s and O’s practice session, Will dozes off while wearing complete head-to-toe grape Air Jordan V sneakers and jumpsuit. He dreams he’s in a small gymnasium, playing one-on-one against the Detroit Pistons’ Isaiah Thomas, who is decked-out in his complete home uniform and a pair of low-top Asics basketball sneakers. The Fresh Prince and Isaiah battle head-to-head for ultimate supremacy in this hazy dream sequence. Will fantasizes about taking him to the rack and swatting every attempt he makes at a layup. This perennial All-Star gets rejected more than a nerd looking for a prom date. As the scene comes to a close, we realize Will is actually dreaming about his very own sneaker commercial. As Isaiah asks, “How do you do it, Prince? Will responds with, “Hey, easy Isaiah…” and the announcer comes in with “Air Fresh gym shoes. Just pass it to Will!”

Bo Jackson – “Someday Your Prince Will Come (Part 2)” – Season 1 / Episode 9

“Aye yo, Bo knows this (what?), and Bo knows that (what?), but Bo don’t know jack, cause Bo can’t rap.” Well, what do you know? Bo can’t act either, but that never stopped an athlete from making a guest appearance on The Fresh Prince of Bel Air. Bo’s introduction occurs during the commercial for the episode, featuring Will rocking the black and blue Air Jordan V jumpsuit and Bo looking mad tough in triple-pleated dress slacks and a tucked-in alphabet soup style shirt. He’s doing his best to intimidate Will for not mentioning his name more prominently in the show’s billing. He eventually breaks a smile when Will changes his monologue to, “Starring Bo Jackson, Bo Jackson, Bo Jackson.” Bo was never portrayed as a much of a tough guy prior to this promo, in-fact, his persona was actually really playful and self-deprecating in his tongue-in-cheek Wieden + Kennedy “Bo Knows” Nike commercials. But with all due respect to the writers of Bel Air, when athletes guest-starred on the program, they always played the role of Will’s physically-imposing adversary, so this characterization fit the mold.

“Someday Your Prince Will Come” is a two-part star-studded affair with a host of guest stars, including Bo Jackson, Quincy Jones, Al B. Sure, Malcolm Jamal-Warner, and sneaker legends, Heavy D and Kadeem Hardison. Will and Carlton are both vying for the same date for Hillary’s Halloween party and trying to impress her by one-upping each other with stories about how hard they ball. Will plays dirty and makes up lies about all the famous people he’s friends with, and goes into a fantasy flashback where Bo Jackson stops by the house to ask for recipe and entertaining tips, where Will refers him to Heavy D for guidance. Will’s outfit is notable here for his pairing of the Bo Jackson Nike Air Trainer SC with the full Air Jordan flight suit.

Ken Griffey Junior – “Love Hurts” – Season 5 / Episode 9

Will becomes embarrassed when his girlfriend finishes a bowling alley fight for him. What started with a smooth brother in Girbaud’s and a mock turtle-neck trying to swoop up on his girl, ended with Will getting knocked out from a sucker-punch. This incident apparently becomes the talk of the town, because somehow, Ken Griffey Junior, playing himself, runs into Will at a local Beverly Hills carnival and busts his chops about it. This short cameo seems to have been written in at the last minute, because it doesn’t make any sense and leaves several questions unanswered: What is this carnival? Why is Carlton working the “throw the ball at the stacked bottles” booth? How does Ken Griffey Junior just randomly show up as himself, and how does he know that Will’s girlfriend knocked out his attacker with a karate chop to the head and a kick to the solar-plexus? The episode gets even more ridiculous as Jazz assists Will in staging an armed robbery for him to foil, in order to look like the hero, but then, coincidently, a real armed robber shows up to the same exact location, at the same exact time, and all of a sudden Will learns how to fight, takes him to the ground, and secures his weapon, just as a campus cop arrives, asking no questions whatsoever, and takes the perp to jail.

Kareem Abdul-Jabbaar – “Will’s Misery” Season 5 / Episode 6

When Hillary buys Uncle Phil and Aunt Vivian matching designer mohair tennis sweaters direct from Milan, her parents try to figure out the best way to avoid wearing them. As they come to the conclusion that squirting mustard all over themselves is the best option, a golf ball comes crashing through the kitchen window, interrupting their sweater sabotage. Kareem Abdul-Jabbar comes casually wandering into the yard to retrieve his ball, wearing the same exact sweater as them. This scene is an early example of an “influencer” showcased on television and permeating pop culture. All of a sudden, Phil and Viv’s opinions of this grotesque sweater miraculously change after finding out that an NBA Hall of Famer wears the same one proudly. When assessing Kareem’s acting performances, this certainly ranks well below fighting Bruce Lee and piloting an airplane.

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