Mad Men Season 1 Behind The Scenes Photos (x)

NYMag: Mad Men’s Saddest Affairs

#5. Don and Midge

Bohemian Midge was mistress numero uno at the start of the series, and her relationship with Don illuminated just how broken Don and Betty’s marriage really was. Midge’s artsiness and beatnik pals held a certain appeal, though her eventual descent into heroin addiction made everything that much more tragic. The real misery of Don and Midge’s relationship was just how easy it seemed for Don, how seamlessly he could be someone else, and how damaging that ability ultimately was for him.