Most Infamous Moment: After making several public appearances clearly intoxicated, namely on The Late Show with David Letterman and the Comedy Central Roast of Pamela Anderson, and after a string of drug-related arrests and probation violations, Love was sentenced to six months of rehab for her cocaine use.

Courtney Love has continuously been a hot mess for the better part of two decades now. When she’s clean and sober(ish), she’s a talented musician and an underrated actress, having killed it in films like Man On The Moon and The People vs. Larry Flint. But when she lets her bad girl flag fly (and trust us, that flag’s usually a wavin’), Courtney’s busy feuding with Foo Fighters frontman Dave Grohl, publicly disowning her daughter Frances Bean Cobain on Twitter, showing up wasted for TV appearances and checking into court-ordered drug rehab centers.