4. Lindsay Lohan
Ah, Lindsay Lohan - where to begin? The actress rose to prominent fame at the age of 12 when she starred as identical twins in the sappy Disney flick The Parent Trap, and even more so as a young adult, truly making a name for herself in Mean Girls, Freaky Friday and then Herbie: Fully Loaded. However, Lohan began to get in trouble with the law soon thereafter, pertaining to drug possession and drunk driving, resulting in her taking countless trips to rehab. Things got more bizarre when she was charged with stealing a necklace in 2011, and just this past week, she has been sentenced to 90 days in a lockdown rehab center, as well as 30 days of community service and 18 months of psychotherapy. Violation of these terms will result in a 6-month custodial sentence. Again, Lohan's another talented actress who it wouldn't surprise me to hear a tragic headline about not too far in the future. Hopefully a stint in a locked-down facility might do her some good...