by Lindsey Unterberger

If there is such a thing as rock bottom, we're pretty sure Lindsay Lohan hit it the morning of July 24, 2007. The just-turned-21-year-old starlet was arrested for the second time in three months on suspicion of driving while intoxicated and drug possession. What happened to that sweet little girl we loved from The Parent Trap? Or even the seemingly down-to-earth teen from Mean Girls? Flip through our slide show as we take a look back at Lindsay's yearlong downward spiral. Then rate her bad-girl behavior...

Play the Celebrity Matchmaker: Stars Behind Bars edition, and try your hand at the Celebrity Jailbirds Quiz.