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Weed, Nudity, and a Severed Nipple: 8 Pivotal ‘Mad Men’ Moments from the Past 7 Seasons

It’s the end of an era, itself marking the end of an era: the last seven episodes of Mad Men are upon us. We leave Don Draper and his complex world in 1970 — ten years after Peggy Olson, fresh out of secretarial school, starts work at the Sterling Cooper ad agency.

For many Mad Men devotees, the show isn’t just about the 1960s advertising world, or even Draper’s identity crisis. It’s about human reactions to the most volatile decade that may ever exist. Even more interesting, reactions to this change come from two drastically different perspectives — those fighting for change and those who had reason to resist it the most: the wealthy white men who ruled the world in 1960. And for those of us who are retro-minded, it’s a chance to obsess over the fashion and culture of one of our favorite decades (raise your hand if you’ve ever taken clothing tips from Joan or decorating advice from Megan!).

For the next seven weeks, REBEAT will recap these final episodes, covering everything from history to social issues to fashion. But before we start speculating if Megan is destined for Sharon Tate’s tragic fate or if Bob Benson is Don from the past (or whatever crazy new conspiracy theories flood the Internet), let’s get excited about where Mad Men‘s going by taking a look back at some of the groundbreaking, pivotal, and insane moments that transitioned these characters through the 1960s.

1) “It’s Toasted,” Season 1 (1960)

Nineteen-sixty brought technology to Sterling Cooper in the form of a typewriter, and birth control gave young women a new kind of freedom (though for the women of Mad Men, their mileage varied). It also brought the first serious public warnings about the dangers of smoking. Yet our stalwart ad men show us just how much they continue to rule the world, considering the threat of cancer a challenge to find a better way to sell more cigarettes. To Don, “This is the greatest advertising opportunity since the invention of cereal.”

2) Peggy smokes weed and Roger wears blackface, Season 3 (1963)

Set against the backdrop of the civil rights movement, and eventually JFK’s assassination, generational values start to clash in 1963. Mad Men masterfully plays these two worlds against each other as Peggy tries marijuana in the office… while Roger performs a minstrel song in blackface at his Kentucky Derby party. After getting over the pure shock of seeing someone in blackface, take a close look at the audience reactions: they’re a good indicator of who moves ahead with the times and who stays behind.

3) Peggy bares all, Season 4 (1965)

It’s called Mad Men, but it’s really all about the women. By 1965, Peggy Olson has come a long way from the eager secretary she was in 1960. She’s now Copy Chief, one of few women with any power in the giant sausage factory of Sterling Cooper Draper Pryce. Holed up in a hotel with a boorish colleague to finish a pitch, the sexism ascends to new heights as Peggy is taunted for being uptight and ashamed of her body. By this point in the show, we saw a lot of shocking things, but Peggy’s unconventional and uncharacteristic challenge to her coworker was mind blowing.

4) Don listens to the Beatles, Season 5 (1966)

https://www.youtube.com/watch?v=afddyqxT1To

Don’s concern about the generation gap increases in 1966. While Roger and his young second wife dive right into a Timothy Leary-esque guided LSD trip, Don struggles with the changing times. Concerned about being left behind, Don asks his own young second wife to help him get up to speed on youth culture, which she does by handing him the groundbreaking Revolver album and telling him to start with “Tomorrow Never Knows.” Don tries, but fails to embrace change.

5) Martin Luther King, Jr.’s assassination, Season 6 (1968)

https://www.youtube.com/watch?v=pDro9pQ2AbI

Mad Men addressed a number of historical events over the previous 5 seasons, but had only touched on race relations — perhaps expected considering the minimal and superficial level it would have impacted this group of white professionals in the mid-’60s. The two issues came together in Season 6 with the announcement of Martin Luther King, Jr’s murder. The news reaches them as they’re enjoying the height of privilege and wealth at an advertising award ceremony, and the variety of reactions is fascinating and, for some, highly unexpected.

6) Don’s breakthrough, Season 6 (1968)

In Season 1, the question, “Who is Don Draper?” captivated audiences, and the answers we discovered hooked us in. The former Dick Whitman had built an entirely new identity around fear and escapism, and by 1960 he was so far removed from authentic human emotions that he was smugly pontificating, “What you call love was invented by guys like me to sell nylons.” Yet, eight years later, the real Don (or Dick) finally reveals himself… at the most inappropriate and awkward possible moment. It costs him a huge account, his reputation, and potentially his job. But it’s a victory: for the first time, authenticity won out over artifice. The times had changed, and so, finally, had Don — at least for the moment.

7) Ginsberg gives Peggy a gift, Season 7, Part 1  (1969)

This is the weirdest moment of the show since that secretary ran over a guy’s foot with a tractor back in Season 1. Ginsberg’s plunge off the deep end was surreal, freaky, and just plain gross. Though many have argued that this went too far beyond the bounds of reality for Mad Men, it certainly got people talking, and introduced yet another change that began in the late-’60s — the advent of technology. But shock value aside, it highlighted that even for the younger generation, the speed of change could be stressful and unsettling.

8) “My Way,” Season 7, Part 1 (1969)

https://www.youtube.com/watch?v=_nHz2uSGgrg

After a season of tension, anger, and power struggles, the two characters, whose journeys are at the heart of Mad Men, finally make their way back to one another. Peggy shares her fears as she reaches the landmark age of 30, and Don, building on the honesty he started cultivating in Season 6, nakedly confesses that his greatest fear is “that I never did anything, and that I don’t have anyone.” After nearly a decade of fighting to be recognized, Don recognizes that Peggy’s talent is equal to  — if not greater than — his own, as he passes the torch to the next generation.

Do you have a favorite Mad Men moment? Tell us in the comments!

Erika White
Erika White is simply obsessed with music and culture of the '60s and '70s. Her writing focuses on the Beatles and the incredible fandom that has kept their legacy growing for five decades and counting. Erika is also a graphic designer, musical theatre geek, rabid Whovian, and Anglophile who lives in the NYC metro area. Check out her Beatles website and follow her on Twitter.