10 Times Mad Men Became The Weirdest Drama On Television

10. That Time Roger Serenaded His Wife In Blackface

Oh, the things Roger Sterling will do to impress a woman. Granted, Roger hasn't always been the most respectful of lovers - there was that time he rode a model around the office like a horse, for example, or all those times he told various women simply to "shutup" - but, when he knows he's onto a good thing, Mad Men's resident silver fox breaks out the charm. Nowhere is this more evident than in the season 3 episode My Old Kentucky Home, which sees Roger pulling an Al Jolson by smearing his face in black paint and singing My Old Kentucky Home to new wife Jane in a way that can only be described as 'uncomfortably racist'. Like most great WTF Mad Men moments, the weirdness of this one is largely down to how abrupt it is. Up to this point, Roger had shown some casual signs of racism, but in My Old Kentucky Home he reveals the true extent of his bigotry, and what's really awkward is how everyone acts as though this is completely normal.