Courtney Love

Well, the above picture says it all, doesn't it? It all began early with this one from admittedly having abused heroin while pregnant with her daughter to relentlessly embarrassing the poor 19-year-old Frances Bean Cobain with her drug-addled lunacy. Courtney Love is probably the unchallenged winner of this list. 

11 years after Frances' birth, she lost custody after overdosing on oxytocin and being charged with possession of the drug. The two have always had a relationship that's been embroiled in controversy, with young Frances even getting a restraining order against her increasingly-erratic mother. In an oddly paradoxical mother-daughter relationship, it's always Frances who remains tight-lipped about it all, showing tremendous maturity, while Courtney Love does what she does best, in full public view--get consistently messed up and looking and behaving like a raging drug addict.