The 10 Kookiest ‘Mad Men’ Conspiracy Theories


Ah, Mad Men. You puzzle us, you entertain us, you alienate us — and you send us scurrying down rabbit holes of hyper-analysis, historical research, and wild conjecture. Creator Matt Weiner’s insistence on maximum secrecy (and comically mysterious teasers) has led, rather directly, to the show becoming a repository for some of the Internet’s wildest conspiracy theories. Here are the ten kookiest.

Megan Draper is Sharon Tate.

The Internet went bananas this week for this notion, which started (as these things so often do) on Reddit and was further developed over at Uproxx, which has kind of become your one-stop shop for Mad Men theorizing. It goes like this: at the end of this week’s episode, Megan is seen wearing a white T-shirt with a red (Vietnam) star. That shirt was worn by Sharon Tate in a 1967 Esquire photo shoot; a Twitter conversation between photographer William Helburn’s daughter and Mad Men costume designer Janie Bryant confirms that this was “no coincidence.” Tate was, of course, the wife of filmmaker Roman Polanski, murdered in her home (along with four others) in 1969 by members of the Manson Family. So this week has seen a flurry of Internet chatter about the Tate/Polanski shout-outs this season, from Sally reading Rosemary’s Baby during a home invasion to the cops on the Season 6 poster to the rise in violence and general dread. So is the show setting Megan up for a Tate-like murder? “After all,” notes Jezebel’s Tracie Egan Morrissey, “Tate wasn’t murdered until 1969, but something else happened to her 1968 — she got pregnant just as her acting career was taking off.” Or was the shirt merely an attempt to show her wearing “something political,” as Bryant has insisted?

Don Draper will die this season…

Before the season premiere aired, our own Judy Berman noted, “Mad Men Season 6 is on what ’60s kids might have called a full-on death trip,” seizing on the metaphor of the season premiere’s title (“The Doorway”) and explaining how “the episode never stops reminding you of death, with even children dispensing unsettlingly morbid dialogue.” A few days later, Uproxx’s Dustin Rowles ran down ten explicit clues from “The Doorway” that hint at Draper’s demise, from the Dante consumption to the references to Paradise (and Paradise Lost) to the near-death of the doorman to Don’s broken watch (“Don’s ticker has died”). Maybe we’re not leading up to Megan’s death — maybe it’s Don’s.

… and it’s secretly the show’s last.

But if that’s the case, wouldn’t that fly in the face of this being Mad Men’s penultimate season, as Weiner has said — since, after all, if Don Draper (or Dick Whitman, or whomever) dies, where would the show go from there? How would the show spin on? Back to our resident Mad Men expert, Judy Berman: “We don’t have one more season ahead of us. Matt Weiner has been punking us all these years. This is the last season of Mad Men.” Noting how the Season 6 premiere mirrors the structure of the show’s pilot, she writes, “This isn’t just similar to the series premiere; it’s an inversion, suggesting the completion of the show’s cycle — the beginning of the end… Weiner is such a fierce guardian of the show’s secrets that, this year, he demanded that critics redact from their reviews the hilariously tame revelation that SCDP had expanded to a second floor. Who says he hasn’t enlisted AMC in yet another one of his elaborate deceptions in the service of a surprise series finale?”

Sylvia Rosen is Elizabeth Taylor (in BUtterfield 8)

Since this is the year that gave us Room 237, it probably shouldn’t come as a surprise that the Internet (again, specifically Uproxx) went wild trying to guess at the super-secret hidden meaning of Don and Sylvia’s days-long hotel tryst occurring in Room 503. Here’s the most entertaining theory: add up the three numbers and you get 8, which leads you to the Elizabeth Taylor drama BUtterfield 8. Sylvia’s look, the way she uses the sheets, the composition of the scene — all recall the opening scene of Taylor’s film, in which she plays a prostitute (and that’s basically how Don treats Sylvia in the episode). Does the BUtterfield scene take place in Room 503? No, it wouldn’t be that easy. But as Uproxx’s Rowles writes, “if you Google ‘Butterfield 8’ and ‘503’ you get this image of a record with Gloria’s theme from the movie. Note the ‘E-503’ on the right.” And that, friends, is a little peculiar.

Pete Campbell is on the road to suicide.

Shorty after the Season 5 premiere, Robin Sayers took to Salon with a prediction: “Pete Campbell will take a header out a Time & Life Building window, probably around Thanksgiving on the show. (I’m iffy on the when but feeling solid on the who, what and where.)” She was certain that Pete (not, as we all have probably assumed, Don) was the falling man in that iconic opening credit sequence, and cataloged an exhausting 75 references to windows, death, falling, and Pete in that episode alone. The theory picked up traction throughout the season, as viewers sifted through new episodes (and old ones) for clues. Weiner claimed none of this was intentional, but purposeful or not, it ended up being a red herring: Lane Pryce, not Pete, was the partner who committed suicide that year — and not by jumping, but by hanging (though that was foreshadowed in a rather grizzly fashion).

Joan Holloway is the mother of the title character in Secretary.

Uproxx’s Dustin Rowles again, with what could either be a fun little shout-out Easter Egg (á la Ted’s consumption of a 30 Rock -inspired “Old Spanish”) or an impressive bit of potential crossover: “Christina Hendricks’ plays a sexy secretary, whose name is Joan Holloway. Maggie Gylenhaal plays a sexy secretary named Lee Holloway in the movie Secretary. In the movie, Lee even has a mother whose name is Joan Holloway. The movie is based on a Mary Gaitskill short story, and Gaitskill is exactly the kind of writer you know that Matthew Weiner is reading. If Joan has a second child, maybe with Bob Benson, and names it after Lee Garner, then we’ll know exactly what Weiner was doing.”

Bobby Draper is a changeling.

Don’s daughter Sally has been played, from the first season onward, by Kiernan Shipka, a wonderful young actress who has crafted the character’s turn from a typical moppet to one of the show’s most compelling characters. But no such luck for the actors playing younger son Bobby — all four of them. Since the boy has transformed three times with no one noticing, it must stand to reason that he is a changeling — a fairy, troll, or elf offspring that is secretly left in the place of a human child. Sure, this doesn’t explain why he’s transformed three times without his parents, step-parents, or siblings noticing, but c’mon: you don’t pay much attention to Bobby either, right?

Bob Benson is a government spy.

Before the Megan/Sharon thing popped up, this year’s biggest object of suspicion and conjecture was Bob Benson, the ever-cheery coffee-fetching new accounts guy at Sterling Cooper Draper Pryce Cutler Gleason Whatever the Hell. He’s always smiling, and always watching; what the hell is wrong with this guy? Well, there are theories. The most compelling — which originated, no surprise, on Reddit — is that Benson is one of Hoover’s boys. “I think he’s a G man,” writes user Oscar_Rowsdower. “The FBI was worried about espionage and there is a war and Dow Chemical is a client, and SCDP has done political work. It wouldn’t be a stretch at all. He’s trying too hard to get close to them. He’s not writing copy or submitting art. He’s not bucking for a position. He’s sucking up and gifting. I predict Benson will get close to Pete, ask about Don, and Pete will spill the Heinz beans about Don’s past. It would go with this season’s poster too.”

Bob Benson is a psycho killer.

That’s not the only wild theory about Mr. Benson’s motives. Others claim he’s a reflection of Don Draper (specifically, the younger version who pestered his way into a job), that he’s Don Draper himself (initials! B.B. and D.D.!), that he’s Don’s secret son, or that he’s Don’s known son Bobby, traveling through time (no, seriously). Now that the Megan-is-Sharon-Tate theory has been floated, popular thinking is that Bob is the demented killer who will brutally slay her — after all, there must be a raging psychopath behind those smiling eyes, right?

Don Draper is a psycho killer.

Then again, considering that Don Draper harbors violent tendencies and has lied for years about his very being, is it possible that he could make the leap to murderer? In discussing Pete’s possible Season 5 death, Jezebel’s Tracie Egan Morrissey made this astute observation: “While Don is supposedly much happier in his new life with his new wife this season, there have been some dark undercurrents in his story. Like when he strangled a woman to death in his dream. Or how about the two different historical massacres that have played into the storylines this season? The first murderer, who raped, tortured and killed eight student nurses was Richard Speck. The second (mentioned on last night’s episode), who killed 16 people — including his wife and mother — was Charles Whitman. Richard Speck. Charles Whitman. Richard Whitman. Dick Whitman. A few weeks ago when the Speck murders were on the front pages of the papers in the Mad Men universe, Sally asked her step-grandmother why he killed those student nurses. ‘Probably because he hates his mother,’ she answered. Dick Whitman was born to a hooker and raised by a stepmother. When he found out, through his half-brother, that she died of stomach cancer her said, ‘Good.’ Dick Whitman definitely has unresolved mother issues.” Ending the show with Don Draper on a killing spree might not make much sense tonally, but it would sure throw viewers for a loop, right?