Philadelphia

Philadelphia

He was a star athlete, sure, and he was about to become a multi-millionaire many times over, yeah, but back in 1996, Kobe Bean Bryant was just a high school kid like any of us were. He sat through homeroom, he studied hard for finals, and he needed a date to his senior prom. Of course, unlike you or I, when Kobe needed a date to his prom, he just looked for the nearest multi-platinum-selling, multi-platform-performing teenage R&B star. Hence, the storybook romance of Kobe and Brandy was borne on May 24th, 1996.

Well, maybe not quite storybook. The two insisted that they were little more than friends, and that Ms. Norwood was just glad to get a chance to act out a teenage fantasy that her celebrity lifestyle prevented her from experiencing organically. (Sadly, no YouTube record exists of the two's magical evening--the sight of a teenage Black Mamba slow dancing with Brandy to Celine Dion's "Because You Loved Me," eyes closed, hands maybe drifting a little further south than comfortable...no price would be too great.) 

Over the next few years, they could be seen supporting each other
throughout their various ventures, Brandy cheering on Kobe at the '97
Slam Dunk Contest, Kobe cameoing in an episode of Brandy's TV show Moesha.
Both eventually would pursue other romantic interests, however, with
Kobe meeting eventual wife Vanessa in 1999 and Brandy engaging in torrid flings with Ma$e and the whiny
dude from Boyz II Men before eventually settling down with producer Robert "Big Bert" Smith in 2002.

 

One could argue that in addition to drifting off personally (in a 2004 interview with MTV, Brandy claimed she hadn't talked to Kobe in "so long"), the two's careers took divergent paths as well. After peaking in popularity in the late-90s with #1 hits "Have You Ever?" and the semi-classic Monica duet "The Boy is Mine," Brandi hit a lull in popularity midway through the 00s from which she never fully recovered. While Kobe continues to play at an elite level and compete for NBA championships, Brandy has to resort to debuting a rapper alternate-identity, named "Bran'Nu." Yikes.

Don't hate too much, though. Girl had some jams back in the day.