2 / 27

Lindsay Lohan

HIGH: LiLo Breaks Into Modeling (1998)
Did you know that Lohan was a model for Calvin Klein Kids and was also the face of Abercrombie Kids in 1998? (Her face appeared on shopping bags just like this one.) We're guessing a casting agent must have tracked Lindsay down after she made her riveting Letterman appearance.

Lindsay Lohan Is 27: Relive Her 27 Highest Highs and Lowest Lows

LiLo turned her 27 on July 2, 2013. Take a look back at some of the best and worst moments from the actress's life so far.