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The Most WTF? Moments of ‘Mad Men’ Season Six

How Don Draper and co. blew our minds this season

Most WTF? Moments of Mad Men Season Six

Mad Men's two-hour season premiere culminated on January 1st, 1968, ushering in one of the most turbulent years in American history. Series creator Matthew Weiner even told Rolling Stone he felt 1968 "was, as far as I can tell, the worst year in American history since 1863." And if this season is any indication, art has imitated life to the fullest, as Mad Men peppered its episodes with some of the most alarming, mind-blowing moments the show has produced to date. It was a year that thrust the Sterling Cooper crew onto the front lines of the Martin Luther King Jr. and Bobby Kennedy assassinations and the riots at the Democratic National Convention – but these instances of historical turmoil were easily overshadowed by the disturbing events of the Mad Men characters' personal lives.

By Sarene Leeds

Kiernan Shipka as Sally Draper on Mad Men

Michael Yarish/AMC

Sally Catches Don and Sylvia Mid-Coitus

Episode 11, "Favors"

Here we thought Sally's age of innocence was tossed out the window when she caught Roger receiving an oral examination from Marie Calvet. Boy, were we wrong. Nothing can compare to the sheer revulsion of walking in on your father getting it on with not only a woman who is not his wife, but the mother of your current crush. Sally had snuck into the Rosens' apartment to retrieve an "I like you" letter for Arnold and Sylvia's 19-year-old son, Mitchell, but she left with a damaged soul – and Don, having unwisely rekindled his affair with his downstairs neighbor, lost the love and support of the one female he still trusted and respected. Most likely forever. No longer can he weasel his way out of such compromising situations by calling what he did "comforting Mrs. Rosen," because Sally isn't a naïve little girl anymore. She sure as hell didn't need to grow up in a brothel to get the same tawdry life lessons as her father.

Jon Hamm as Don Draper on 'Mad Men'

Jamie Trueblood/AMC

Don Smokes Hash

Episode 10, "A Tale of Two Cities"

Don Draper at a Hollywood Hills party? What's next? Roger Sterling smoking LS . . . never mind. Don putting his lips to the nipple of a hookah may not have been as groundbreaking a TV moment as Roger's acid trip last season, but it was plenty bizarre as he hallucinates a longhaired, hippie-ish, pregnant Megan (fueling even more online conspiracies that the character will be murdered à la Sharon Tate – which Matt Weiner has debunked) and a dead Pfc. Dinkins (the Vietnam soldier Don met in Hawaii), who was relieved of an arm while in combat, not to mention his own death. As Don watches his body floating in the pool, a soaking-wet Roger, who jumped in to save him, smacks him out of his reverie. That Don, he can't even elude the shadow of death while on drugs.

Jon Hamm as Don Draper January Jones as Betty Francis and Mason Vale Cotton as Bobby Draper on Mad Men

Michael Yarish/AMC

Don and Betty Sleep Together

Episode Nine, "The Better Half"

Don's still mourning the end of his affair with Sylvia, so what does he do? Instead of reconciling with his own oblivious wife, he goes the other route, hopping into bed with his newly slimmed down ex-wife while the two of them are upstate visiting Bobby at camp. There was nothing sweet or romantic about it, as these two have been worlds apart for years – even before Mad Men began in 1960. If anything, it proved how much Betty has wised up to her former husband's sexual patterns, lamenting Megan's sorry predicament: "That poor girl," she says. "She doesn't know that loving you is the worst way to get to you." By the next morning, Betty presents herself as the valedictorian of the Don Draper school of "This Never Happened": She is happily eating breakfast at the rustic motel diner with Henry, coldly ignoring Don as he's relegated to a single table.

Elisabeth Moss as Peggy Olson on Mad Men

Michael Yarish/AMC

Peggy Accidentally Stabs Abe in the Belly

Episode Nine, "The Better Half"

Tensions are flaring up not just in the streets during the summer of 1968, but in the Olson-Drexler household as well. After Abe is stabbed in the arm getting off the subway – and refuses to rat out the kids who did it to the cops – Peggy's not feeling so safe in her new lovers' pad. So when she hears screaming and glass breaking outside her own window one night, she's got a crudely fashioned spear (a kitchen knife strapped to a broomstick) at the ready. Except her victim ends up being her own boyfriend as her reflexes are quicker than her eyes. But all Peggy's unintentional violence did was bring on the inevitable: In the ambulance, radical journalist Abe breaks up with his borderline Establishment girlfriend, saying her 'activities are offensive to my every waking moment. You'll always be the enemy."

Davenia McFadden as Grandma Ida Kiernan Shipka as Sally Draper and Mason Vale Cotton as Bobby Draper on Mad Men

Jordin Althaus/AMC

‘The Crash’

Episode Eight

This episode was so jam-packed with off-the-wall incidents that it has to be given its own placement in the WTF? Moments Hall of Fame. The majority of the characters spent it strung out on a concentrated vitamin cocktail injection that new partner Jim Cutler ordered up to increase productivity. It results in Ken Cosgrove doing a tap dance, a kiss between Stan and Peggy – and Don's drug-induced visions of his even more sordid past. When teenage Dick Whitman caught a cold, the only person who would tend to him was a blond hooker named Aimee Swenson, who then took his virginity once his fever broke. Oh, and there was that whole interaction between Sally and the kooky African-American intruder who tried to pass herself off as "Grandma Ida" before making off with a bunch of valuables.

Jon Hamm as Don Draper and Linda Cardellini as Sylvia Rosen on Mad Men

Courtesy of AMC

Don and Sylvia’s Hotel Room Tryst

Episode Seven, "Man With a Plan"

Sylvia Rosen is no Anastasia Steele, that's for sure. A couple of days locked in a hotel room, commanded to give Don his shoes on her hands and knees and being told "You exist in this room for my pleasure" drained the fun and excitement out of this affair faster than Sylvia could even utter a safeword. This wasn't the first time Don has exhibited D/S tendencies (remember when he tied Bobbie Barrett to the bed?), but his desire to treat Sylvia as little more than an object is what forced her to put the kibosh on their arrangement. As she prepares to return to her cuckolded husband and stop seeing Don once and for all, she chastises him for degrading her: "It's easy to give up something when you're ashamed."

Don Draper Jon Hamm Roger Sterling John Slattery Ted Chaough Kevin Rahm and Jim Cutler Harry Hamlin Mad Men

Michael Yarish/AMC

SCDP merges with CGC

Episode Six, "For Immediate Release"

For Don, the Holy Grail of advertising accounts has always been a car company like Chevrolet. When he finally gets the opportunity to pitch Chevy, the battle is lost before it's even been fought. Once Don and his nemesis, Ted Chaough, realize they're both going after the automobile giant, they know Sterling Cooper Draper Pryce and Cutler, Gleason and Chaough will cancel each other out. So over drinks in a Detroit bar, Don and Ted decide to pitch Chevy together, effectively merging both companies. The bombshell is dropped on Peggy in the final scene of the episode, when her former and current bosses announce she'll be moving back to her old work digs and she will once again be working under the mercurial Don Draper.

Elisabeth Moss as Peggy Olson and Kevin Rahm as Ted Chaough on Mad Men

Michael Yarish/AMC

Ted Kisses Peggy

Episode Six, "For Immediate Release"

Peggy's decision to move in with her boyfriend, Abe Drexler, last season had disaster written all over it – her mother was furious, Peggy was disappointed there was no ring in the offing, etc. But as the sixth season opened, it seemed that cohabitation was suiting Peggy just fine, until Abe persuaded her to buy a fleabag apartment on the then-dangerous Upper West Side and the romance began a steady decline. Complicating matters was the out-of-left-field smooch that Peggy's boss, Ted Chaough, planted on her during a late night at the office. But Ted's impulsive action sparked a yearning that, frankly, we haven't seen Peggy demonstrate with Abe, well, ever. If one kiss can cause you to start fantasizing that your boyfriend is your boss in a smoking jacket, then maybe you're with the wrong guy, Peggy.

Vincent Kartheiser as Pete Campbell on Mad Men

Michael Yarish/AMC

Pete and His Father-in-Law Run Into Each Other at a Brothel

Episode Six, "For Immediate Release"

Getting caught cheating on your wife? Mad Men's been there, done that. But running into your father-in-law while you're cheating on your wife? Now that made for some jaw-dropping television. Ever since his disastrous affair with Beth Dawes last season, Pete's marriage to Trudy is hanging on by a thread, so it wasn't a surprise to see him at a brothel with fellow mystery accounts man Bob Benson. Seeing Tom Vogel, on the other hand, was not on the agenda. As usual, Pete was the one who ended up with the short end of the stick. Invoking a common double standard, Tom chastised his son-in-law for hurting his precious daughter, saying nothing of his own infidelities, and he summarily withdrew his account, Vick Chemical, from SCDP.

Christina Hendricks as Joan Harris and Teyonah Parris as Dawn on Mad Men

Michael Yarish/AMC

Joan Awkwardly Hugs Dawn

Episode Five, "The Flood"

The news of Martin Luther King Jr.'s assassination affected every character, young and old, black and white, in "The Flood." But it was Joan's misguided attempt at solidarity with Don's African-American secretary, Dawn Chambers, that brought the sole moment of levity to what was a very somber episode. When Dawn arrives at the office the day after the news broke, Joan doesn't hesitate to throw her arms around her colleague. Dawn's confused reaction and lack of reciprocation encapsulated the confusion felt by all Americans during that time, and Joan's "We're all so sorry" put a nice comic button on the scene, as if Dawn knew Dr. King personally because of her skin color. It was such a WTF? moment that it quickly went viral – in the form of a GIF file.

Jessica Pare as Megan Draper on Mad Men

Ron Jaffe/AMC

Megan Tells Sylvia She Had a Miscarriage

Episode Three, "The Collaborators"

It didn't seem out of the ordinary to Megan, but for the viewers (who knew that her friend and neighbor, Sylvia Rosen, was having an affair with Don), watching Mrs. Draper confide in her husband's mistress that she had a miscarriage was painfully awkward. The disclosure was made all the more stunning when Megan stuck it in between updating Sylvia on her soap opera plot lines – even the audience thought she was talking about her character at first! The scene made it even harder to develop any sort of sympathy for Sylvia's predicament when she allowed her staunch Catholic upbringing to cloud her ability to offer Megan comfort. Megan was relieved when she lost the baby – she'd even contemplated abortion, neither of which Sylvia could support.

Jon Hamm as Don Draper on Mad Men

Michael Yarish/AMC

Don Pitches a Suicide-Tinged Ad Campaign

Episodes One and Two, "The Doorway"

Between Don reading Dante's Inferno, the passing away of Roger's mother and shoeshine guy, the switching of lighters with Vietnam-bound Pfc. Dinkins and countless other examples, the Season Six premiere was fraught with death. But nothing brought Don Draper closer to the opening-credits image of a man falling from a building than his latest ad campaign for the Royal Hawaiian hotel. His slogan of "Hawaii: The Jumping Off Point" was plastered across a sketch of a man's jacket, tie and footprints on the beach, leading toward the water. Don viewed it as a man freeing himself, but the clients – and anyone else with a pair of eyes – saw a man committing suicide. It was one of the first times when Don was incapable of closing a deal with his powers of persuasion, and it was the apex of an episode that promised a season of mortal reminders lurking behind every corner of Don's existence.

January Jones as Betty Francis on Mad Men

Jordin Althaus/AMC

Betty Suggests That Henry Rape Sally’s Friend Sandy

Episodes One and Two, "The Doorway"

It's improbable the word "likable" would ever be used in the same sentence as the name "Betty Francis," but even this sick joke was uncharacteristic of Betty's prior cruel and selfish comments. It started off innocently: Betty and Henry are making harmless small talk about Sally's visiting violin-prodigy friend, Sandy. Out of nowhere, Betty offers up the idea of her husband raping Sandy while Betty "holds her arms down." Henry is just as creeped out as we are, but there's a perfectly good explanation for Betty's kinky idea: "You said you wanted to spice things up." Obviously this is not what Henry had in mind, and Betty's mischievous smile at the end of the scene hints that she was just messing around, but it still left a bad taste in everyone's mouths.