35. Miley Cyrus
Most Infamous Moment: In 2011, following years of growing up on the Disney channel, Miley was caught on tape referring to herself as a pothead and smoking salvia.
The former Hannah Montana has tweeted half naked photos (on more than one occasion), took a topless photo shoot for Vanity Fair at 15, had photos of her giving fellatio to her boyfriend's penis-shaped birthday cake, and got engaged to said 22-year-old boyfriend at 19. This must have broken her dad’s achy breaky heart.