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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

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.