5. "Bleecker Street," Simon and Garfunkel. Season Four, Episode Seven: "The Suitcase"
"The Suitcase" focuses almost entirely on the complex yet tender working relationship between Don and Peggy as they work all night on a Samsonite campaign. This elegiac song off of Simon and Garfunkel's debut album, Wednesday Morning, 3 A.M., is a stinging reminder that while Don gives off an aura of success and power at the office, when he goes home at night, it's no longer to his wife and children but to an empty apartment in Greenwich Village. This loneliness is punctuated even more when Don learns the news that Anna Draper, the one person in the world who truly knew him, has succumbed to cancer.
6. "(I Can't Get No) Satisfaction," the Rolling Stones. Season Four, Episode Eight: "The Summer Man"
One of the more brilliant facets of Patsavas' music selections on Mad Men is she tends to avoid going for the obvious choices (the only Beatles song reference the entire season is an instrumental cover of "Do You Want to Know a Secret?"). That doesn't happen in "The Summer Man," where she chose to open the episode with one of the most indelible riffs of 1965, if not the entire decade. But it works perfectly, even though conservative Don is probably the last character that comes to mind when thinking of the Rolling Stones. After a swim at the New York Athletic Club – in his attempt to lead a healthier, more sober lifestyle – Don hears Keith Richards' fuzz guitar quietly emanating from a nearby transistor radio. As Don exits the club, the song is at full volume, punctuating Mick Jagger's lament over not getting any satisfaction – which the buttoned-up Don can certainly relate to, as he gazes at the younger, cooler masses gliding by him.
7. "I Got You Babe," Sonny and Cher. Season Four, Episode 13: "Tomorrowland"
It's the song that left us hanging and clamoring for more, as Season Four concluded with Sonny and Cher's simplistic ode to their love. We all know how well that relationship turned out, making the song choice an ironic one: "I Got You Babe" plays over an awake, pensive Don while his brand-new fiancee (and his children's preferred source of maternal comfort), Megan, sleeps nearby. Given the abrupt and unexpected nature of the proposal – and Don's track record with women – the odds aren't good for the supposedly happy couple. After all, the last time a SCDP man married his secretary, it only drove him straight back into the arms of his faithful office manager.
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