Lindsay Lohan first hit it big in 1998 with her starring role – technically two starring roles – in the Disney film The Parent Trap. She played two 11-year-old twin girls, which took an outstanding amount of skill to act out. However, even more notable was her positively adorable charm and iconic freckles, which made her an instant favorite amongst child stars. Her career progressed with several other hit films, but most popular of them all was the more mature film, Mean Girls, in 2004. It was greatly acclaimed, and her older looks made her stunning. However, drugs and booze are the great stumbling block for many Hollywood stars. In and out of rehab, along with the stress of dealing with arrest records for a variety of things, all took a toll on her good looks.