Ranking All of Will Smith Girlfriends on Fresh Prince 

Derrick Deane
Updated June 14, 2019 22.9k votes 2.8k voters 109.6k views 20 items

He may not have been Jerry Seinfeld, but Will Smith certainly had his fair share of lovely beauties visit the Bel-Air mansion. (If you're interested in Will Smith's sex life, here's a list of bedroom secrets he's shared!) Here, we've gathered together a list of the Fresh Prince's girlfriends from the entire run of The Fresh Prince of Bel-Air. From Lisa and Jackie to other Will girlfriends played by famous actresses like Pam Grier, Vivica A. Fox, and Vanessa Williams, they're all here!

Who did Will date on Fresh Prince? Lots of ladies, to be sure. Who could resist his charms? Whether for just one season, or an entire multi-episode character arc, there were lots of girlfriend characters who came in and out on Fresh Prince, but if you are trying to remember that one girl from that one episode (you know, the one who was a boxer maybe?) they are all here for your nostalgia fix and trip down '90s television memory lane.

So take a look at ladies that caught Will's eye and, yup, turned his life upside down. Which are your favorite Fresh Prince girlfriends?

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Nia Long as Lisa Wilkes
Lisa Wilkes is listed (or ranked) 1 on the list Ranking All of Will Smith Girlfriends on Fresh Prince
Photo:  Wikimedia Commons (CC-BY)

Fun fact: Jada Pinkett-Smith, Will Smith's wife in real life, was originally supposed to play Lisa Wilkes, but she was too short. In stepped Nia Long, who starred as Will Smith's girlfriend-´╗┐turned-fiancé, Lisa Wilkes. 

Lisa is the girl who comes in and "tames" Will; he reforms from his womanizing ways to be with her. Their relationship makes Will believe in monogamy and true love for the first time, and he proposes. They almost get married twice - once in Vegas, and once at a planned ceremony - but they both realize that they have too many doubts to go through with it. 

In earlier episodes, such as season two's "She Ain't Heavy," Long played the role of Claudia. When Long was selected to play Lisa Wilkes later on in the series, the character of Claudia was replaced by Raven-Symoné.
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Tyra Banks as Jackie Ames
Jackie Ames is listed (or ranked) 2 on the list Ranking All of Will Smith Girlfriends on Fresh Prince
Photo:  Wikimedia Commons (CC-BY)

Tyra Banks played the lovely Jackie Ames, one of Will's recurring friends on the show. Jackie and Will grew up together in West Philadelphia, and they haven't seen one another in three years.

Initially, Jackie is upset because Will hasn't called her in so long, but she eventually forgives him when she learns that he didn't call because he missed her too much. Jackie moves out to LA on a basketball scholarship for the University of Los Angeles. She gets a job at the campus store, the Peacock Stop, and hires Will to be one of her employees. Will reveals that he and Jackie once hooked up back in Philly, but Jackie maintains that they are still just friends.
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Elise Neal as Wendy
Elise Neal as Wendy is listed (or ranked) 3 on the list Ranking All of Will Smith Girlfriends on Fresh Prince
Photo: Metaweb/CC-BY
In the season four episode "M Is for the Many Things She Gave Me," Elise Neal plays Wendy, the daughter of one of Uncle Phil's ex-girlfriends. She and Will hit it off, until Will is seduced by her mother, Janice.
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Lela Rochon as Cindy Norris
Lela Rochon as Cindy Nor... is listed (or ranked) 4 on the list Ranking All of Will Smith Girlfriends on Fresh Prince
Photo: flickr/CC0
In season two, Will secretly starts working at a pirate-themed restaurant in order to save up money to go to the school dance with Cindy Norris, played by Lela Rochon. Uncle Phil offers to pay for him, but Will doesn't want to end up as spoiled as Carlton. In the end, Uncle Phil realizes that there's nothing wrong with a little hard work, and Will realizes that there's nothing wrong with accepting help from your family on your way to success.
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