Lane Pryce certainly got in over his head in the most recent season of 'Mad Men,' unable to repay debts and stealing company money to cover his ass, but Lane was a charming fool. His affection for Joan and concern over her possible prostitution to land the company the big Jaguar account stole our hearts, and let us forgive his other mistakes, like his aforementioned financial stumbles that could have destroyed Sterling Cooper Draper Pryce. But the guilt of what he'd done was too much to bear, and in order to keep his family afloat and spare his mistakes from affecting others, Lane hung himself in his office in one of the series' most shocking and heartbreaking moments.

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