20. Lindsay Lohan
From child star to mugshots in orange jumpsuits, public breakdowns and rehab, there would have been a time not too long ago when Lindsay Lohan would have easily been at the top of our list of the hottest redheads in Hollywood.
Launching her career as a child fashion model at just three years old, Lohan made her television debut at the age of 10 with her motion picture debut to follow a year later in Disney’s blockbuster hit The Parent Trap.
Transforming from the mischievous freckle-faced redhead in The Parent Trap into a teen idol, Lohan landed roles in films like Mean Girls, Herbie: Fully Loaded and Just My Luck. Since then, however, things have taken a turn for the worse as the 29-year-old has turned to drugs and alcohol. With her addictions taking a toll on her health and her looks, we only hope our favorite mean girl gets back on the right track since she has plenty of time to make a huge Hollywood comeback.