A boy with Philly swag and Bel-Air money had no problem wooing enough girlfriends to fill six seasons of The Fresh Prince Of Bel-Air . From his high school years to his college days and beyond, Will entertained many a lady-friend, some more successfully than others. Will's list of ladies is a veritable who's who of up-and-coming stars. Dating The Fresh Prince provided a high-profile stage for so many women of color to showcase their comic chops. And I'm not just talking about actresses: Musicians, radio personalities, models — all of the above made cameos on the sitcom to romance Will (and/or drive him crazy).
The show revolved around Will's relationship with his cousins, the Banks family. Even so, many of the most memorable episodes of The Fresh Prince have something to do with Will's love life. He was trying to get the girl, keep the girl, or get rid of the girl, and each and every one of those women gave him a run for his money. To pay tribute to the women in Will's life, I've selected the six freshest girlfriends The Fresh Prince ever had. Whether they held court for one episode or an entire arc, these ladies and the cocky star were well-matched.
6. Tyra Banks As Jackie Ames
America's Top-est Top Model Tyra Banks played Jackie, a girl from back home who surprised Will by matriculating at the same So-Cal college as him. (And being his no-nonsense boss at the school store.) Knowing him for as long as she did, Jackie came equipped and fully defended against all of Will's moves. In fact, they were far too alike to ever really make it work.
5. Tisha Campbell-Martin As Kathleen
Will learns an important lesson about diving in the deep end without an on-duty lifeguard when he gets trapped in a basement with his new lady, Kathleen. After irritating his entire family with their icky obsession with one another, Will and Kathleen's delicate balance is the first victim of the earthquake that derails their date. Campbell-Martin has an unparalleled stank-face in this episode, and Will's impromptu serenade can still reduce me to tears.
4. Robin Givens As Denise
She's not technically a girlfriend — Denise was more of a seductress, dead set on compelling Will to stray from Lisa. But, no one can play discomfort quite like Will Smith did in those days; Denise gets a spot on this list just for making him squirm.
3. Pam Grier As Janice
Family boundaries go up in flames when Will hooks up with one of Uncle Phil's old love interests. He was intended for Janice's daughter (an also radiant Elise Neal), but the Mrs. Robinson fantasy was too much for Will to resist. Can you blame him?
2. Nia Long as Lisa Wilks
Excuse me, Beulah Wilks. Lisa was Will's longest lasting girlfriend — a fun but practical girl who could keep her man in line. They almost tied the knot twice: once at a Shaft-themed Vegas wedding (which is the dream, obviously), and once at a big church wedding that their parents decided to use instead.
1. Queen Latifah As Dee Dee
I've never stopped 'shipping this. National Treasure Queen Latifah was so funny and charming as Will's pal Dee Dee; she should have stayed forever. That moment where the two spot each other sporting matching nose-straws from across a crowded room is legitimately one of the most romantic scenes in '90s comedy. Trust.
Images: Warner Bros. Television; freshprincesubs (2), spacecadet, femburton/Tumblr
