Remembering ‘Mad Men’: The UPROXX Staff’s Favorite Moments

For seven seasons, Mad Men took us on a tour of the 1960s, undercutting the eras supposed tranquility by presenting characters with inherent urges and failings, before showing the vague discomfort felt by those same characters as they started becoming culturally obsolete whilst trying to guide the conversation about what is and was cool.

Will we miss the characters — the con man who built a god for himself (and his baggage) to inhabit, the glutton who grew a soul, and the ceaseless dreamer — more than we miss the clever dialogue and the bold storytelling? The style more than the substance? We’ll need a little time away from Mad Men before we can properly answer that. But for now, the Uproxx staff has gathered up our favorite moments from the show’s iconic run. We’ll start with mine.

Though I was tempted to go with Don’s recent realization in the McCann boardroom that he was not nearly as special as he thought, or the time that he reminded Ginsberg of his insignificance (“I don’t think about you at all”), or… I ultimately wanted to go with a more personal moment, and there’s none more personal than Don and Peggy’s first last goodbye in Season 5.

Frustrated and finally eager to spread her wings, Peggy tells Don that it’s time for her to move on. There are so many words in this exchange, as Don smirks and assumes this is some kind of game while Peggy visibly braces herself and continues to rebuff his half-hearted apologies and his offers of more money. After a few moments, when Peggy once again stands firm and goes to shake Don’s hand, we see him realize that this is real, and we see his desperation and hear him say, “Don’t go,” as he holds her hand and kisses it gently. She holds back tears and amazingly evades the emotional pull of an obvious plea from a man who’s been like another father to her. It’s an amazing moment, and it’s one of so many from the history of this show. Here are our picks, make sure you tell us what yours are in the comment section.

Ryan Perry 

It’s impossible to choose from the dozens of Mad Men moments that ignited earnest feelings within me without gushing like a lunatic, so instead I choose to salute the shorts of the show’s delightfully mysterious, ass-kissin’, Pete Campbell-instigatin’ fraud: Bob Benson. While his “NOT GREAT, BOB!” moment in the elevator with Pete was great, Bob peacocking around Joan’s apartment in his short shorts to the disgust/envy of Roger was peak Bob Benson:

Danger Guerrero

One of the complaints you’ll hear about Mad Men, usually from people who don’t watch the show, is “nothing happens.” This is hooey. The following things have happened on Mad Men: A secretary ran over a man’s foot with a riding mower she was driving around an office, in a high-rise, in Manhattan; a man cut off his nipple because he thought a computer was turning him gay; a man tried to poop on another man’s office furniture; a fist-fight broke out in the office because a prostitute left chewing gum on a client’s “pubis.”

And one day, an executive called in his personal doctor to administer pharmaceutical-grade amphetamines to the staff by injecting it into everyone’s butts, sending everyone on a drug-fueled, episode-long escapade. It was so weird. That was the episode. Everyone was just on drugs for an hour. It wasn’t my favorite episode of the show from a plot and character development standpoint, but it was … it was so, so weird. I love that they did it.

Jamie Frevele

I honestly don’t know what could be more satisfying than Pete Campbell being punched in the face. Lane punching Pete in the face feels so good to think about AND watch because he’s gotten nothing but weasly over the course of his time on the show. I don’t know if I’m ready to accept being happy about him getting to punch someone himself (even if that punch was directed by Jared Harris), but there was something kind of poetic about it.

And Sally calling her mother “Betty” always cracks me up.

Chet Manley 

The stairs! His butt! It works on so many levels!

Pete Campbell was one of the more sniveling f*cks on Mad Men. Whenever he got knocked out, was ridiculed by Bob Benson, or threatened by his wife, it was all well deserved. This particular moment combined malice towards a character and classic slapstick with hilarious results.