Her Hollywood Resume: The current poster-child for problem children in Hollywood, Lohan started off her career as a kiddie actor in movies like 1998's The Parent Trap and 2003's Freaky Friday before graduating to more mature flicks like 2007's I Know Who Killed Me and 2010's Machete.
Her Musical Efforts: Outside of acting (and partying!), Lohan has found time to release two solo albums: 2004's Speak and 2005's A Little More Personal (Raw).
How Well She Crossed Over: Both of Lohan's albums sold remarkably well, but is that surprising considering how popular she was back in the mid-2000s? Let's just say that neither of these are still on our iPods—or anyone's iPod—today.