'Mad Men' Season Five's Most Depressing Moments

We run down the season’s lowest – but no less intriguing – points

Roger and Jane’s acid trip – Episode Six, 'Far Away Places'

jane and roger
Jordin Althaus/AMC

Between Roger Sterling's continued infidelities with Joan Harris last season and his endless sniping with his wife, Jane, this season ("Why don't you sing like that?" "Why don't you look like [Don]?"), the demise of the second Sterling marriage was hardly a surprise. Still, it was no less sad to watch Roger and his trophy wife reach clarity about their dead-in-the-water relationship while under the influence of LSD, despite the matching hot-pink towel turbans. Their disconnect was sublimely illustrated by their inability to even share hallucinations together. Roger could see the 1919 World Series from their bathtub, but Jane couldn't.

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