Rihanna

We know we’d be hard-pressed to find an awkward photo of Rihanna. But it seems like the Fenty Beauty owner is simply too photogenic to be caught off-guard. She was already a known singer when she attended her prom in the late ‘00s, but she reached the peak of her stardom years later.

Producing hit after hit— from Umbrella to Love On The Brain— she cemented herself as a pop star to reckon with. Now, she’s also proven herself as a capable businesswoman. Thanks to the success of her fashion and beauty empire, Rihanna was declared a billionaire in August 2021.