Lindsay Lohan

One of the saddest falls-from-grace in Hollywood comes by way of Lindsay Lohan, who was, at one time in her career, loved by so many. The popular Hollywood actress’ sweet performance in Parent Trap, as well as her iconic role in the pop culture hit, Mean Girls, earned her the adoration of fans, sealing her as one of the business’ hot stars. Sadly, this didn’t last long as she has spiraled out of control since then, being in and out of jail for various reasons such as DUI, assault, and cocaine possession.