Gwyneth Paltrow and Brad Pitt
Two classic 1990s actors, Gwyneth Paltrow and Brad Pitt caught themselves in the middle of a photo leak scandal in 1997. They were vacationing together in St. Barts and decided to layout in the nude in their private garden. Of course, the paparazzi showed up to snap some pics and the photos were released to the British tabloids.
Erin Heatherton
The Victoria's Secret model walked the runway from 2010-2013 and even collaborated with major fashion houses like Tommy Hilfiger, Michael Kors, and Valentino. She previously dated Leonardo DiCaprio, and some of her nude photos during their relationship were leaked. They were very personal photos and were stored on her own cell phone.