Paris Hilton

Claiming a critical success, Paris Hilton starred in a Peacock reality series, “Paris In Love,” in 2021 and launched her production company in the same year. Remaining in the public eye for decades cannot save a celebrity from unfortunate moments, and Hilton was also caught by one.

On one event in 2008, someone photographed the Hilton Hotels heiress singing at a karaoke bar. Feet up and nestled comfortably on a sofa, it looks like she probably had one too many drinks that evening. Unfortunately, as Hilton sang her heart out, she sank further into the seat, and her dress began to rise; the resulting image was not very flattering.