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Strongly Recommended
The only reason this show isn't Trope Overdosed is that it makes an effort to be fresh and unpredictable. Mad Men is well-constructed, engaging, and steeped in sophisticated social commentary. If you can, imagine a Joss Whedon series without the action or the Speculative Fiction. Indeed, you'll recognize several actors and writers from Whedon productions, and the pilot is eerily similar to the unaired pilot of Firefly.

Fair warning, Mad Men is dark, and frequently upsetting. It's a challenging show, full of literary references and Genius Bonus (it helps if you lived through the events, of course). And if you dislike modern feminist critique, you may feel alienated. One tip: feel free to laugh. There's black comedy at every turn.

My uncle worked in just such a company, and found the show to be painfully accurate. It's uncompromisingly anvilicious in its depiction of the blithe, ingrained sexism whose legacy is still very much with us, and the general lunatic decadence of mid-twentieth-century corporate culture. For me, an American two generations removed, it's a history lesson, but I've also found plenty to empathize with—Peggy's struggle, fresh out of college, to break into a professional world she does not in the least understand, and Don's difficulty accepting the privileged life he knows he doesn't deserve.
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