Kobe Bryant and Brandy

Both just 17 years old in 1996, Brandy and Kobe Bryant were each other’s date to the late NBA star’s prom. Although they were already famous at the time, it was the Moesha actress who was the bigger star then. Born into a musical family in Mississippi, she shot to fame in the early ‘90s with the success of her self-titled debut album.

Meanwhile, Bryant, the son of former basketball player Joe Bryant, began his climb to the top after being drafted by the Charlotte Hornets and, later, the Los Angeles Lakers. Unfortunately, his life was cut short in a fatal helicopter crash in January 2020.