Person to Person

A conversation on the Mad Men Finale

Welcome to day one of Together, Alone. To celebrate our debut, we're publishing three pieces today. Starting Thursday, we'll begin our weekly publishing schedule.

Arielle: It’s such a perfect series finale. I always get emotional watching it. I think I love it more with every re-watch. Every time I do, I wait on the final episode because I don’t want it to end.

Gabe: What was it like coming back to the last episode after a wait like that? 

A: You know, I think because I’ve seen the whole series a few times, it flowed really smoothly for me. How about for you? Had you re-watched Mad Men in its entirety? Or just the final episode?

G: I watched the whole series when it was new, and would revisit episodes from time to time, but finally started a re-watch in 2021. The finale felt a lot different the second time. When it was airing new, there were so many expectations, so many theories, that I almost couldn’t take in the episode itself. 

A: I always had a complicated response to Mad Men. I loved so much about the show but there were things about the cultural reception to Mad Men that bothered me. A lot of fetishizing of Don Draper’s behavior, for example. I think I’m able to see the series a bit more accurately now. I also am just struck by how much I have changed since first seeing those initial episodes way back in 2007.

G: The cultural response was new for me. In one sense, it seemed odd to find thrift stores selling themed costumes, and cocktail specials for viewings. But on the more exciting side, it was the first show I remember reading recaps for. Before that, thinking deeply about a TV show was a little nerdier than it is today. Talking seriously about TV was something trivia nerds or pop culture obsessives did.  To see the reaction to the show be so communal was refreshing.

A: For me too! It was very much a shared viewing experience that hasn’t quite been replicated since. One of the most interesting aspects of rewatching now is not having those commercial breaks. I remember watching with other people and we’d all be waiting to see what happened next. Didn’t the show air at 7 and 9? I’m trying to remember.  

G: It definitely aired again that same evening. I remember taking a walk after the “Love Among the Ruins” episode, which opens with the scene from Bye Bye Birdie. I could hear the song playing through open windows on my block. 

A: That’s such a lovely memory. 

G: It really stuck out to me—and Twitter at the time was full of reactions. I’d stay off if I couldn’t catch an episode live. I’m curious, when you say you see the series more accurately now, how do you see it? I was surprised at how much more critical it seemed of not just the era, but the industry and media. But that might be my bias.

A: I think I understand more of what it means to experience fast cultural change than I did when I first started watching the series. When I first watched, I found the sexism excruciating to watch and I was angry that so many characters didn’t make different choices. But I think I’ve developed more empathy for the experience of being “stuck” in a time period because now I’ve experienced some of that too. How many articles today focus on Millennials feeling out of step now that we aren’t the youngest generation on the block? We are always somewhat “adrift” in whatever cultural experience everyone is having. 

G: Definitely. Before the re-watch, I hesitated, wondering if I was just trying to recapture some of that feeling of youth after not loving a lot of the newer shows I was streaming (maybe a point to revisit, but the show is paced so differently than newer shows). The episode “The Monolith” really hit differently. Harry Crane replaces the creative lounge with a computer. It felt very similar to my experience in the journalism industry—“this new digital tool will do your job better” and the way it makes it better is to make it more mechanical, more predictable, more data-driven. To see it now, that I wonder if maybe the writers had been commenting on the shift in their industry that was happening. 

A: Yes! I felt a lot more compassion for the characters trying to keep pace with all this change than I did the first time around. And the acting is just so phenomenal. You really feel for every single character and their journey, which is one of the reasons the finale really worked for me. 

G: I loved the finale, but my interpretation of the ending was different this time. When Leonard, the middle-aged man in the blue sweater, speaks up in therapy and says he feels invisible, Don hugs him. Then the next day, Don is dressed in white and comes up with the iconic Coke commercial that incorporates all these countercultural images. This time through, I saw it as Don recognizing that he, like many aging adults, felt out of step with where the culture was going. And to turn it into a soda commercial seemed like a cynical move.

A: It’s a pitch perfect combination of cynicism and hope. For all that Don learned to be reduced to a commercial to sell sodas! And yet, Don is really in despair. When he is on the phone with Peggy, you don’t know if he is going to make it. He has always survived through this kind of storytelling. It’s both an indictment of the industry and a celebration of the human spirit. It’s unsettling in the best way.

G: That’s a great point. I found an interview where Matthew Weiner said he’s not cynical about the ad, but the episode is all about people finding peace with work—the storytelling saves Don, you’re right. Joan chooses her career. Peggy, Stan, Pete, even Roger. They all find comfort with their own personal “work-life balance” as we call it today. 

A: I felt so bad for Joan. She’s a tremendous character and I love how she is doing what she loves, but, man, no one was really there for her in the way she deserved.

G: He told her “your life is undeveloped property” in an early scene! I never caught the weight of that line before, and it really hit me this time. He seems to see it as his property to develop. 

A: Yes, for sure. And then to not have that partnership with Peggy. 

G: Peggy stays on track to be a creative director by, as Pete says, 1980. 

A: When Joan is in the kitchen with the color TV, I was like, we are getting into more familiar pop culture territory. I can see the ‘80s right around the corner!

G: And Sesame Street is on! Back in the office, I could see Peggy’s impatience with Pete at that 1980 line—to still have to wait. 

A: What do you make of her decision not to partner with Joan?

G: I think it fits with her character to a degree—she’s able to rise to the top and doesn’t seem to be satisfied until she proves it. But it also seems like what she wants to do is to write advertising, not produce corporate films.  

A: Yes, that makes sense. She stayed with what she knew and loved. She wanted to get into advertising way before Joan decided to pursue this new dream. I’m very interested in the cultural reception of the female characters in Mad Men. Peggy was hailed as a kind of “feminist girl boss” the first time the series aired. And Betty’s character was so deeply hated, even though she really suffered a great deal. In many ways, Don and Betty’s relationship is at the heart of the show. When Don’s voice cracks saying, “Birdie” on their last phone call–wow. 

G: Oh yeah—it seems like it’s the part of his past he can’t force himself to move beyond, and those earlier seasons when they were together made it clear that he doesn’t really understand her, either. I remember around the time when both Mad Men and Breaking Bad were going, a critic addressed the audience hatred for both Betty and for Skylar in Breaking Bad (I wish I could find a link). But the point was basically that it’s a lose-lose situation for the characters. They’re married to these gruff antiheroes and either they try and steer them back and seem like obstacles or they join and become villains. 

A: Oh yeah, I wrote about that too. I was fascinated by the anti-Skylar hate. And I always had a soft spot for Betty in a way that I  think a lot of people had for Don. I think this time around, I felt more for Don and his journey. 

G: Ah! It must’ve been your piece! On Don and his journey, and connecting back to the Coke ad, it hit me this time to see Don suffering so much to get ahead in what ends up seeming like kind of mundane work. Advertising can be powerful, for sure, but all the arguments around the office about the best way to sell beans or luggage. That might be my age playing into it, too. When I first watched it, I was much more of a young careerist, and now I’m more burned out and less likely to relate to being so fixated on a minor work issue.

A: Yeah, I forget which episode ends with that Peggy Lee song, “Is That All There Is?” And I agree–it’s one of the reasons I feel sorry for Joan’s lack of a true partnership. She deserves to be loved! And this new business venture is wonderful and clearly what she wants to do, but all these industries are just terrible and inhumane in many ways.

G: They’re so wrapped up in work that outsiders wouldn’t really care about. Ken says “I can’t be eclipsed again by Plastics & Packaging” like it’s the end of the world. But then it’s such a great reveal at the end that Joan gives the business two of her own names and is taking charge.

A: Yes, I love that! I would totally watch a spin-off with her business. Speaking of spin-offs, do you remember the meme of Don selling Pepsi in the ‘90s? Could this show get a reboot?

G: I an see Don pitching a campaign for Crystal Pepsi, or the Coke response—a terrible-tasting clear version of Tab that was meant to sabotage Pepsi by making people dislike clear cola. I was thinking that, in my non-Matthew-Weiner-approved reading of the ending, Don’s way of thinking won. In the arc of the show, he goes from being challenged by the counterculture to turning it into fodder for ads. It sets the stage for the ‘90s in a way, for big department stores to market flannel shirts just a few months after Nevermind became a hit. 

A: Absolutely. And I kept thinking about our current fascination with cults when watching the characters on Mad Men try to “escape” mainstream culture and find a life with greater meaning. 

G: That retreat! “Psychotechnics, Divorce: a creative experience.” It was set around the time that Bob & Carol & Ted & Alice would’ve come out, which has a character experience a kind of spiritual awakening at a very similar retreat, only to find out he’s not really as into the counterculture as he seemed. 

A: Haha. It’s both cringe and also…I really felt for middle age sweater guy! I love his monologue. It makes me cry every time I watch it. 

G: He was so good. When I was rewatching, I picked up a copy of Natasha Vargas-Cooper’s book that gives footnotes to Mad Men episodes, but sadly it was published in 2010 and there was no new edition. But even the limited time the book covers gives a lot of background on that rapid change you described, and how even the tiniest pieces of normal life would’ve been totally upended for someone like him. I wonder, do you think the view of the show now would be shaped by the “OK Boomer” style of generational interaction now? 

A: Oooh, that’s interesting. What do you mean by that? The young people on the series do seem to throw jabs at Don about how he is “old.” Do you mean how today’s viewers would respond?

G: Yeah, I wonder if it might seem a little more celebratory of that era or that generation, even as it shows their flaws. Don isn’t technically a Boomer, I suppose, but he shapes the culture. And for as clear as all the flaws are, some of the sets and costumes are so eye-catching. I wonder how a first-time viewer would react—would they see it as nostalgia, the way people seemed to around 2007 or so, and reject it over that? Or are we in a different place where that kind of reading is less likely?

A: My guess is that Don would be seen as less “aspirational” if the series came out today. I don’t think people would be having parties and copying the outfits. I think more people would see Don as toxic. But the truth is, I think the power of the series is that Don is both well-meaning and a person who has caused great pain. You have to be able to hold both things in order to get something out of the series. Kind of like BoJack Horseman, another series I love that encourages both empathy and accountability.

G: I loved BoJack, too, in large part for that complexity and the way it made me feel to watch the episodes and puzzle through (that’s a show where I can’t bring myself to watch the ending yet). Are there other protagonists like that now? 

A: Oh, we should discuss the ending together!

G: Coming soon to Together, Alone! 

A: I think we are seeing a lot of antihero backlash right now, partially because a lot of people believe that the antihero condones bad behavior. The characters on Mad Men are often infuriatingly cruel. I wonder if viewers today would have less patience for that.

G: There does seem to be a closer connotation between the culture someone consumes and the moral values they have. Beyond even thinking a character condones bad behavior, almost an impression that watching that character is an endorsement of it. I have a feeling that’s going away, but maybe I just see it less because I’m not on Twitter as much. 

A: I feel like I see some backlash to antihero backlash on Twitter right now. 

G: It does seem like, if you’re looking for a show to make you think about morality and progress, Mad Men is a good option.

A: I do think I’m able to tolerate difficult and, at times, frustrating antihero characters more today than in 2007. But it’s hard for me to separate how much my original response to Mad Men was shaped by the discourse at the time the show came out.

G: It’s interesting to think about aging with a show—something that seems to have risen out of the era of binge watching and streaming. I remember having conversations about the show with colleagues and family members who were alive at the time it was set, and they often had different responses. But I think maybe that’s more a sign of where they were in life than when they lived. I wonder how the show will play when I inevitably watch it again in six or seven years. 

A: I personally plan to not get any older over the next seven years so my response will likely be the same! Just kidding, this is honestly why I love rewatching. Every time I revisit an older text, I see how much I’ve changed. I feel like it helps me chart my own journey over time. 

G: Same. I look forward to our next conversation!