Who Are the 5 Saddest Characters from Season Two of Mad Men?

Don and Betty Draper might be the most tortured couple on television. Last season we felt sorry for Don when he had to sleep on the floor at Betty’s dad’s house because he was in the dog house. And yes, seeing the usually stylish Betty chain smoking in a muumuu, trying to break into Don’s desk to find evidence of his affair was pretty sad. There’s also Don’s secret past hanging over him, and Betty’s permanent existential crisis. But strangely, in our humble opinion, they weren’t the ones who elicited the most pathos last season on Mad Men. Find five even sadder characters after the jump.

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1. Chauncey

Alas, poor Chauncey. When Duck Phillips’ ex brings the family dog to Sterling Cooper for a permanent stay, you can tell it ruffles Duck’s feathers. When Chauncey gives the former alcoholic the stink eye as he ogles a bottle of booze, you know he’s a goner. Later in the episode, Duck abandons him outside of the office building.

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2. Freddy Rumsen

One day you’re playing Mozart on your zipper, the next you’re fired for pissing your pants and passing out before a big pitch meeting. We’re pretty sure that Freddy’s “six-month absence” will be permanent; nothing was sadder than watching him drunkenly stall as Don tried to put him in a cab outside of the underground club.

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3. Glenn Bishop

If there’s anyone who can make us sadder than universally scorned divorcee Helen Bishop, it’s her son Glenn. In love with a woman that will never do more than hold your hand? Check. Going through that pre-pubescent awkward stage? Check. Think running away to a neighbor’s playhouse actually counts as a running away from home? Bingo.

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4. Hoss

When Marilyn Monroe dies, Sterling Cooper’s elevator man sums up the tragedy (and in a prescient way, the entire series) succinctly: “Some people hide in plain sight.” This is a man who has known sadness. He’s also likely the most emotionally intelligent person on the show and rare gets to speak. Note: The image above comes from a different episode wherein Hoss gamely rises above Paul Kinsey’s “you’re black, meet my black girlfriend!” social awkwardness.

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5.  Kitty Romano

We spent most of “The Golden Violion” episode that Kitty featured prominently in debating whether or not Salvatore Romano’s wife actually realizes that she’s married a gay. Regardless, Kitty senses that she’s invisible to him that can’t feel too good. Neither can watching another man sample your husband’s sauce…