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Mad Men’s Most Shocking Moments, Season by Season

Last night's Mad Men featured one of the show's more disturbing moments. Spoilers follow for this week's episode.

Ginsberg, in the throes of a severe mental health crisis, presented Peggy with the gift of his severed nipple. Shocking! Gross! And totally in keeping with Mad Men's affection for gross and shocking moments. Let's go back season by season through some of Mad Men's most surprising instances of violence, grossness, depravity, and all-around surprise.

Season One
Surprises abound in season one, starting with the pilot, where we learn that Don's beatnik girlfriend Midge is in fact his beatnik mistress Midge. Don's whole backstory comes as a surprise, and his brother Adam's suicide is the first of many jarring deaths on the show. All of season one is get-to-know-you time, really, so each piece of character development — be it Pete's sliminess, Peggy's mysterious pregnancy, or Joan and Paul's history — feels particularly revelatory. But among this generalized feeling of newcomerness, two instances stand out as notable outbursts: Betty shooting the pigeons in "Shoot," and Don orchestrating Roger's barf attack in "Red in the Face." The image of the perfectly perfect Betty, cigarette in mouth, shooting BBs at the neighbor's pigeons is one of the first (but absolutely not the only) times that we see Betty snap under the pressure of having to be how other people want her to be, instead of getting to be herself. Even more shocking, though, was the moment two episodes earlier, when a very flushed, very fatigued Roger Sterling horked up two orders of oysters. Don was exacting revenge on his boss after Roger flirted with Betty; he took Roger to lunch and ordered a lot of rich food and a few gallons of martinis, and then paid off a building employee to claim the elevator was broken, forcing the men to haul ass up the stairs to their important meeting. Oysters plus running equals a sad, messy, and yes, very surprising moment.

Season Two
Season two on the whole is less shocking but more engrossing, though there are some surprises along the way: Don's relationship with Bobby Barett provides a few jaw-droppers, Joan's fiancé raping her in Don's office is the exact kind of shock that's always crushing to see, and an unhappily pregnant Betty having anonymous sex in a bar is something most of us never saw coming. On the (sort of) lighter side of things, Freddie Rumsen pissing himself in the middle of an alcohol-induced blackout is certainly stunning, but the biggest WTF moment comes courtesy of one Duck Phillips. It took Peggy a while to figure out Duck was no good, but we've known since "Maidenform," when Duck cruelly — and for no real reason! — abandoned his handsome, loyal pooch Chauncey. Mad Men's not a particularly animal-intensive show, so moments like this, with poor Chauncey being shoved onto the streets of Manhattan, are even more striking.

Season Three
If Roger Sterling in blackface doesn't surprise you, I don't know what will. "My Old Kentucky Home" isn't just making the point that 1963 was a long time ago; it's also reinforcing that Roger Sterling is way out of touch, since plenty of people found blackface appalling and offensive in 1963. (Even Pete is horrified. Pete!) Joan smashes a vase on her piece-of-crap husband's head in "The Gypsy and the Hobo," Pete rapes his neighbor's nanny in "Souvenir," and two hitchhikers kick the crap out of Don in "Seven Twenty Three," but of course the most shocking moment in season three is from "Guy Walks Into an Advertising Agency." Hell, that's one of the most shocking moments of TV in living memory: Lois drives a riding lawnmower over Guy's foot at Joan's going-away party. Gaaaaaah.

Season Four
For a high-art show, there's a lot of vomiting on Mad Men: In "Public Relations," it's Sally's turn, and she chucks at the Thanksgiving table, mostly to spite Betty. (Later this season, in the "The Suitcase," Don also barfs, though it's not really much of a shock.) Parental abuse is a recurring theme on the show, and in "Hands and Knees," we learn Lane, too, is a victim when we see his dad — who is pretty old and otherwise feeble-seeming! — whack Lane with his cane. It's tragic and humiliating, and while we see adults on this show punch and brawl occasionally, an old man using his cane to assault his adult son is unusual. But two moments in season four's "Beautiful Girls" have that gasp-inducing oh-no feeling that embodies the best Mad Men surprises; first, Mrs. Blankenship's death at her desk, and the subsequent farce of trying to keep that hidden, and second Sally Draper wiping out, hard, in the office hallway. Sally's petulant and surly, yeah, but in that moment she's also just a little girl. Seeing a child get hurt is always upsetting, but knowing how much pain Sally's already in makes it more wrenching.

Season Five
Season five is full of violence and foreboding and death imagery, and of course Lane's suicide seems like the most important part — but we knew that was coming, so while it's sad, it's maybe not the biggest shock. (More surprising, perhaps: Lane clocking Pete right in the face.) Peggy's anonymous hand job in "Far Away Places" is pretty surprising, and many people were stunned that Joan went through with prostituting herself to the Jaguar garbage human, but it's Sally catching Roger and Megan's mother mid-blow job in "At the Codfish Ball" that elicited the sinking feeling. It's not a violent moment, really, but it is ominous; Sally's had a pretty crummy run of things, and watching yet another innocent time become corrupted by the badly behaved grown-ups around her feels so damn unfair.

Season Six
Not even a contest: Peggy stabbed Abe with an improvised harpoon! What!