The Prestige TV Podcast - Did ‘Mad Men’ Stick the Landing?

Episode Date: January 24, 2024

Andy Greenwald is joined by Sean Fennessey to discuss “Person to Person,” the series finale of ‘Mad Men.’ They start by describing what the surrounding culture was like and who they were as people when it initially aired (5:03). Next, Andy reveals that his opinion of the final episode has altered, then details what led to the change of heart (16:00). Along the way, the two talk about how the AMC hit drama decided to handle Don Draper’s send-off and the ways in which it broke so many TV norms in the process (64:22). Finally, they answer the titular question: “Did it stick the landing?” (74:44). Host: Andy Greenwald Guest: Sean Fennessey Producers: Kaya McMullen and Kai Grady Theme Song and Other Music Credits: Giancarlo Vulcano Learn more about your ad choices. Visit podcastchoices.com/adchoices

What would you do if you got scammed? Would you suffer in silence, or would you do something about it? Well, I got scammed once, and this is the story of what I did. I'm Justin Sales, the host of the Wedding Scammer, a true crime podcast from The Ringer. And for seven episodes, we're hunting a comment. A guy with a lot of aliases, a guy who's ruined a lot of weddings. And with the help of some friends, I just might be able to catch him. Listen to The Wedding Scammer on Spotify or wherever you get your podcasts.

From smoke gets in your eyes to person to person, from Don's first old fashion to his last bottle of Coke, 10,000 cigarettes and nearly as many Emmys later. Get the chewing gum off your pubis people. This is Stick the Landing, Mad Men. We are back with another episode of Stick the Landing, a new podcast about endings. My name is Andy Greenwald. I am so thrilled to be joined by my good friend, colleague, style inspiration, Sean Fennacy. We don't do this enough. You and I. Banter on Mike. Yeah. We're plenty in person. I agree. Yeah. We do it person to person, if you will.

That's right. That's right. We're making a connection. Are we having a Stan and Peggy moment here, Andy? Should anyone have a stand and Peggy moment? We're going to debate all that because we're talking about the final episode, episode 92, which is shocking, of one of the greatest series of all time. Mad Men's finale, person to person. I'm very excited. I mentioned to you this is my favorite show.

I'm my favorite show of all time. I appreciate the declarative nature of that because after spending some time this week rewatching a bunch I think you're probably right that it's the best one probably my favorite one too your mileage may vary on what kind of TV show or film you like people talking in rooms

is a very intoxicating elixir for me and this was the pinnacle of that and obviously it came at the time when you know you were writing about all of these shows at this period in time And a lot of them were incredibly good, but this was the one that I had the most fun with on a consistent basis. Also, because on this show, the currency was creativity. And the way that people talked about the struggles between art and commerce and life and work were, and continued to be quite relevant.

Yep. That doesn't make a special, but that definitely makes our connection to the show more intriguing. May 17, 2015 is when this episode aired. It came as episode 14 of a split final season, which is something that used to happen back in the day when AMC was trying to make more episodes spread out over more time, but not paying people more. You know, I was thinking they did just do this for better call Saul.

Yes. You know, but it's not as common as it used to be. No, I think the contracts are done differently. I think the old standard TV contracts were seven seasons. And when they realized that Weiner was done or that they weren't going to be able to retain the services of one Jonathan Ham. They were like, guess what? Seven in 2014, seven in 2015.

Interesting. And so we ended up here. And one of the things I wanted to call out before we kind of get into the context, where we were, where the show was, I did want to at least tip my cap to one of the great innovations of Mad Men, which was its complete refusal to say anything about the episode that was to come. So I didn't check out the Next on Mad Men that aired when the Milk and Honey Root aired on May 10th, 2015. I imagine it was just a picture. I imagine it was just Don saying, what?

And then a car driving next week on Mad Men. It became almost like haiku. Did they even do one for this episode? They probably didn't. I have a faint memory that they didn't even give us one for the final episode. I could be wrong about that. But obviously they were so impressively elusive about any content against the future of the show. Do you know what the log line for this episode was?

Because, again, that would always be like, Peggy raises her hand. Roger has a drink. Something emerges. Don has a long think about something. I mean, they could have just hit copy and paste for seven seasons. This was the stories of Don Draper, his family, and his co-workers at Sterling Cooper and partners come to an end. Oh, that's true. In many ways, it's the most revealing one that was ever written about an episode.

Yeah. It is sort of the death and taxes of log lines. It's like, you know what, at a certain point, it all ends. It all ends. So let's talk about where we were. as a culture and we were as people in May 2015. I think the attention was high on this show, not only because it was fiercely beloved and wildly acclaimed,

but the writing was on the wall at this point about where TV was, where it was going, and how we didn't have a lot of these to take its place. There wasn't a next great serialized cable prestige drama waiting in the wings. So I think there was some, I don't know if it's unwarranted, but there was some extra attention on Mad Men for that reason. I think that you're right.

I think it also was until Succession came along, the last true darling of the literary press. And so because of that, and these shows were sort of similarly small but big, and there was a heaps of attention poured on Succession over the years, including by yourself. The same with the show. The show very rarely broke more than two or three million viewers.

It was just not that big. but it was so clearly elite. It was so clear. It's kind of like the tar of its day where it was like, for those of us who saw it, we were like, this is, this is. Don't suck up to me in the podcast studio. How dare you? Well, I'm sucking up to myself in some ways too. But like, you know, every once in a while, stuff comes along that is critically acclaimed.

And it's acclaim and its awards are enough to power it for a long stretch of time. Yes. And on the more cynical, which is appropriate for a show about advertising side of it, that you could tell that, well, maybe only one to two million people were watching the show linearly on. AMC on Sunday nights, those one to two million people were perceived as viewers who could afford BMWs and imported beer and whatever else. Like listeners of your podcast, you know? Lots of spending power, highly educated, you know, erudite people moving into their 40s and 50s. Do you know that the primary sponsor of this podcast is complicatedly safe?

It is just like a, it is for people who don't want it to be simple. Yes, a true ode to Don Draper. Yeah. It's the least that I can. but none of the safety. See, this is why you're good at podcasting. You keep bringing me back to the text. Well, I try to go leap off a clip at Esselin.

This is my, I'm always kind of making sure we stay on track as much as possible. So you want to get into, should we start by starting with the episode here, or do you want to, like, set a little bit of dual table setting for May of 2015? I mean, I love that you're doing this show because you and have friends in New York, but we became much closer friends when you started, when I started at Grantland, you were already there. And you'd been writing about it. TV at a heavy clip for a few years here. This was always a favorite of yours. You weren't recapping the show per se, but you were writing about it frequently. It was my, it was and probably not that I

do it anymore, but if I look back on writing about TV on a regular basis, this was the best show to write about. It was by far the best show to write about. This is something that you said actually before we had record, but it's the most literary television show of all time. It is a show made by writers about writing in such a, in such a deep way. I mean, and one thing I've learned in the year since is that it is so, so deeply about writing for television, which is the art versus commerce advertising. You can make money by doing this, but what, what about your Ben Hargrave sci-fi? Is it Ben Hargrave, Cosgrove? What's Ken's Ben something? This is his sci-fi alter ego. Oh, I can't even recall.

Doesn't matter. Well, you failed the first test. Sorry. Anyway, I don't watch every episode of this show for this conversation, but a lot of them, I'm going to make a lot of references to one episode in season five that I watched to throw you off. TV writing is in that way. Can we make money doing this, but are we selling out by doing it a conversation for writers to have at this point in time? And the other thing about it was that it rewards and continues to reward very deep viewing on an intellectual and an emotional basis.

We're going to talk about this and we talk about this episode because it is so, so sodden with it, but this is a show made by people who have done a lot of therapy and are ready to talk about therapy and put it in practice. It's also a show that considers every magazine, every book, every image, every composition in reference to whether it's the actual book that they're talking about or, I mean, was the first season finale about a Franco-Hara poem? I mean, it is showing off its English degree to it. Yeah. Was it meditations in an earthquake? An emergency. An emergency, excuse me.

That would be the LA version. It would be meditations in an earthquake. But the other thing was that it just, when you write about anything, and you know this from your time as a. critic as well. When you're taking, you're picking up pieces like action figures from what's given to you and thinking about how they interact with each other, there's so much between each one. You could pull out almost anyone. And I remember having this experience because, again, unlike, I was joking recently on this podcast about how one of my hardest jobs at Granlin was I had to recap the office during seasons eight and nine every week, which may never recover from. Were there 23 episodes in those seasons? Yes, I did all the Thursday night shows every week for Friday. I was in my 30s. There wasn't AI. You guys were monsters.

Yeah. I didn't make those assignments for the record. No, you didn't stop them either. I didn't stop them. But I had a really unique circumstance where we had Molly Lambert recapping because she had been doing that for years and doing it very well. And we had Mark Lassanti doing his brilliant power rankings. So the show was covered every week. So I was able to... Both essential pieces of writing, I thought, at the time. week to week for season after season. And what that freed me up to do was be like the way in the remaining major city newspapers, they have the beat reporter on the team and then they have the columnist who sort of swings in on Monday morning. And it's just like, well, here's the thing about, let's not talk about football because I want us to get along. Let's talk about it.

I mean, I'm getting ready to make some changes in my life when it comes to football. So I know you're not. I don't know why. From my experience, Zach Wilson's a proven winner. I don't know when this is going to air, but I honestly hope he is in Tanzania by the time it does. So I could come in and just sort of pick up something, pick up a bobble and consider it. And I remember writing a piece in one of the final seasons, maybe it was season six, about, season five maybe even, about Megan Draper and the Silver Surfer in Marvel Comics. And it was so rewarding.

Classic Andy right there. Incredible stuff. Truly revealing. But because the show rewarded that kind of attention, kind of watching. So it was deeply pleasurable in that way and enriching. Yeah, I mean, I think the really. reasons that I loved it and that I liked thinking about it so much are pretty obvious, I think, for a man in his 40s in America right now. I really loved the mid-century American fiction. I really

loved the cinema of the 1970s. I really like, I'm a kind of non-creative creative. I work in the world of shoulder content. Everything that I create is relative to what has come before me that I need to iterate on. And it's very confined by what I'm given. And that is kind of the crisis that Don and Peggy have every week is here's this thing. It's something people use in their life, but it is not poetic, put poetry to it. I mean, that's what we do.

Yeah. So I think it has like an overwhelming power for a person in that position. Now, I think it can have an overwhelming power for somebody who digs ditches, for somebody who's a school teacher. I think it is like, well, Don, Don did bet a school teacher this time. Yes, there may be more regret and anger towards the characters if you're from one of those jobs. But, yeah, I mean, it's just right square in the center of our bullseye. emotionally, intellectually.

I was therapist at a young age and then didn't have any therapy. So, like, I was in therapy when I was very, very young. And, like, kind of banked all that. But then never went... I've sought out many shows that explore, like, these psychological characters

and are kind of, like, like you said, like putting forward a lot of the ideas that the writers have been gifted by the people that they've been telling their lives to. So I feel very safe in those kinds of stories. You know, The Sopranos is kind of the B-Sides, or the A side really to Mad Men's B side.

And in many ways the show often felt like Matthew Weiner kind of like writing through his experience of working on The Sopranos along with the network television that he wrote. And I was immersed in all that stuff. I watched network television all the way up until the late 90s and then I watched HBO and that was really my safe space. And then AMC and Netflix and all those other things come along.

And it's part of this like coaching tree, right, of taste and point of view and all this stuff that it feels like we've lost a little bit. But Mad Men was always closest to the center of my personal bullseye. I would also say, just as a side note, famously, a lot of people try to, you know, ascribe autorial presence in the main characters of these shows with their creators. Matt Weiner has at least directly or indirectly made it clear that he often related to Peggy more in circumstances

and that the famous, we're not going to, I promise we're talking about person to person, not the suitcase. In fact, we've done a podcast about the series together years ago. Very fun. Was it me and Amanda? Yes, it was. Famously, that's what the money is for. Don is David Chase in that scene. Right.

And Matt Weiner is Peggy, apparently. I think it's reasonable to assume that many of the characters in the show are characters that Weiner aspired to be. For sure. I think Don, obviously, but I think also in some ways, Betty, I think Roger in many cases. I think that the facility with the response with like the emotional and intellectual clarity that all these characters have is something that we all kind of want. And we're not going to spend too much time psychoanalyzing Matt Weiner, a man who I don't think either of us have ever met. But one thing that stood out to me was the reclamation of Pete Campbell that comes to its fruition in the finale is unquestionably something coming from deep inside of him. Absolutely.

His arc is amazing. And for that character to go from where he begins, drunk outside of Peggy, who he's just met her apartment building in Brooklyn, to literally flying off into the sunset with his perfectly intact family is wild. And I overlooked that at the time. I think that's something that the show does very well, too, if you revisit it now, is you can plug yourself into different characters, kind of crises or points of view or emotional challenges, because obviously they're kind of aging over time as the show is going on, you know, Vincent Carthizer's hairline in particular,

going in all kinds of crazy directions by the time we get to the end of this. Some of which were done intentionally. Yeah, of course. Not all of them. Not all of them. Time, comma, the ravager. Yeah, you know, waste lines expanding and shrinking and, you know, Life happens.

Who among us. But I do think that as I watch, as I revisit the show and revisit the finale, especially, I don't know, I think about how maybe I used to be a Peggy and I'm not such a Peggy anymore. You know, I think that's part of what's fun about it. I totally, totally agree. I think it's in the penultimate episode when Trudy says to Pete, I'm envious of your ability to be sentimental about the past. It's very relevant.

Although I will say I don't know how sentimental are conversation. is going to be today because it's really more about a reclamation and rediscovery. Time has changed my feelings about this episode. Not necessarily about the series, but about this episode in, I don't know if it's profound, if it's only interesting to me, but like what it feels to me to be some profound ways, before we recorded, I sent you a screenshot of a tweet I fired off. Love to get those from you. Love.

Screenshots of tweets are just an elite form of conversation. They're often about like the composition of our Supreme Court. but in this case, yes, it was about Med Men. Yes, and it was my own tweet. I self-tweeted at 8.28 p.m. on May 17th, 2015. Rarely do we get these snapshots, certainly on this show or ever. Did you tweet us like immediately at the conclusion of the series?

Yes. Okay. I mean, I think the show aired at 10 p.m. on the East Coast, and it was about 57 minutes long. So basically, yes. So when you did that, your editor sat there and thought to him, or herself. God damn it, Andy, just write the piece.

I wasn't on deadline. Ah. You should remember, Sean, that my columns ran on Wednesdays. Good point. So I had, so Molly was running on Monday morning, Mark was running probably, he was probably up all night doing it. I had a couple of days, which helped. But I fired off this tweet.

Mad Men is one of my favorite shows of all time. I loved it this morning. I love it now. But I thought that finale was unambiguously awful. I hate Twitter so much. It's an honest reflection of your reaction. But that was my reaction. I'm not proud of it, but I wanted to share it.

Because I have been carrying that for the eight years since. I continued to say Mad Men was one of my favorite shows, but I have continued to just believe in my bones that this episode was very bad. And I have revisited it, and we should just dive in. I no longer think that is the case. I find that pretty interesting. I don't think I had a rapturous appreciation for it at the time. I think I had a lot of sadness that it was over because I really did look forward to this show.

In a way, I look forward to very few things. Honestly, I'm quite cynical about even the things that I love. I'm kind of like, eh, is this going to work? Is this going to be good? It's kind of my nature. You said that before we had dinner one time. Well, you know, it is what it is. But in this particular case, I thought that the final five minutes were an absolute stroke of genius.

And so despite feeling like, like there was a kind of tidiness to this episode. Yeah. It was unusual for the show. I thought most of that tidiness was satisfying. And then the end, the final conclusion, which felt like a fitting rejoinder to the Sopranos finale.

Yes. In a lot of ways to me, I thought it was just brilliant. And also just a brilliant kind of evocation of, for somebody like me who's a real workaholic, kind of how you can never really get away. I just really related. I felt like I really understood what,

whiner was trying to say, I really understood the shape of the Draper character. I really understood that even though the world was changing, some people never change. And I always tell this story about my dad sitting me down when I was about to get married and he was like, I just want you to know, people change. And he's divorced and I was like, this is

fucking brutal, man. I'm getting married in two days. But he was right. He was right. He was being like brutally honest with me in a way that he never did. And my dad is very post-Draper-esque in so many ways too. Like an Irish Catholic, taciturn, strong. A lot going on under the surface.

You know, like, I always had this real sense of appreciation for the desire to not break the code on Don's arc on this show. I feel like this finale doesn't do that. Let's drill down on that. So what's the code? What's the arc? Because, you know, the Sopranos, I think, is a, it's a very dark show, separate and apart from the violence in it. David Chase has a very low view of human beings. himself included. He has said this. He's on the record.

I think that one of his messages of that show is that people do not change. People, we can try to change people, we can try to change ourselves, but they are immutable objects. How are you saying Mad Men either engages with that or rebuts?

Well, I tell that story about my dad because I think he was like, I changed. He wasn't saying people changed. He was talking about himself, but did he even change? I don't know. I think that's up for debate. The same way that Don, throughout the course of this episode, it seems like, He's having this radical emotional breakdown and rebirth all the way up until the last second of the episode. And then he has a realization in his mind about how to get back to work.

And that is really how many people are. And that is actually, as you said, that is kind of what the Sopranos is about. It is hard to shake who you are. It is hard to evolve. It is hard to progress. It is hard for Don to progress, despite his desire to do so in public fashion. I mean, this podcast is about starting with the end.

I hesitate to start with the actual end moment of this episode, but maybe we already have and maybe we should. The episode ends with Don saying, oh, this is his mantra in the lotus position on the cliffs at Esseland seemingly open now to the possibility of being his true, lived, emotional self, turning the page, as he said, he's wearing white, he's not wearing shoes. It's very, it's full of heavy imagery. He closes his

eyes. A smile appears on his face and we cut to one of the most famous advertisements of all time that I'd like to buy the world of Coke. I still push back on the assumption that he made that ad. Fire away. So this, this, what you're speaking to, I've struggled with. When I did write my column on Wednesday, a piece that I read back and I'm really, I'm really proud of because I feel myself arguing with it, myself in real time, that I was wrong to do the tweet, and I didn't like this. But the more I argue about how much I didn't like it, the more I'm basically Leonard breaking down in a therapy session about clearly if it's making me this upset, there's some emotions. What a performance by Leonard, by the way. Evan Arnold.

Just remarkable. A lot of growing pains on his, not as a performer, but like literally he was on growing pains. And then he was cast in this crucial, crucial part. And all of that I want to talk about, like, the value, like, suddenly introducing Brett Gelman, like, what are we doing at the end of the show, at the end of this road, at the end of the country? I wasn't sure what the intent was. Is the intent exactly as you read it? And I think as we've begun to, this is just now the conventional wisdom about the episode, that that smile means he's going back to McCann, that he's going back to New York, and he has monetized his nirvana. I think not necessarily one-to-one exactly that. But I think that the, the, the, the, you know, the, you know,

use of the commercial as the closing sentiment of the series indicates to me that the arch cynicism that runs through the show is confirmed. Okay, so I'm with you. So if we agree, and there's some interviews with Matt Weiner that he's done, where he basically says, and this is an interview he did, he did this onstage in New York, and it was covered a few, a short time after the episode aired, he said, I have never been clear, and I've always been able to live with ambiguities. Must be nice, Matt. In the abstract, I did think, why not end the show with the greatest commercial ever made? In terms of what it means to people and everything, I'm not ambiguity for ambiguity's sake, but it was nice to have your cake and eat it too in terms of what is advertising,

who is Don, and what is that thing? So I think we can take this two ways. There is no textual evidence that Don Draper went back to McCann and created this ad. In fact, this ad was created in our world by someone else who's not named Don Draper or Dickwood. I think the second point is a more valid one and more interesting one, frankly, which is the show's decision to clarify its worldview and end its nine-season monologue with us, with this image. And I don't know if it's cynical anymore. This is part of the change that I've come to.

Because this is a show that the pilot episode, Smoke Gets in Your Eyes, contains some pretty existential statements for what the show is going to be, that advertising is happiness, that love doesn't exist, love was created by advertising executives to sell pantyhose, nylons, or whatever. What I'm getting at is the ambiguity that Wyner's speaking about to me is kind of profound, which is to say that in being present and alive in a moment on a cliff, Don has achieved some inner peace.

the nature of humanity is to roll ever forward and mix up everything like it's a cocktail. Agree with that. Agree that's part of the intent. I think it can be both. I think on the one hand, it's unmistakable that Don is wearing a white button-down shirt and khaki pants.

In previous scenes, in this episode, he has begun to dress down. He has worn a polo, and then he's wearing a button-up shirt. He's getting increasingly casual. That knit shirt is $200 a corridor right now in Larchmont. Okay. It's a very good point.

Nevertheless, he does not look like the man in the gray final suit, as Don Draper once did. But by the end in the final image of the episode, he's in work attire. And I don't think that's in business cash, but yes. Kind of. For us, it would be considered that. But at the time, and especially at Esselin at that time, whilst sitting in the low disposition, as you pointed out, I don't think that's a mistake. I think it's meant to indicate that we're always kind of working. Yes.

I'm always kind of thinking. I do think what you're saying is true. Maybe it's not Don who made that ad. but the idea of what's happening at Esselin becoming commoditized that the folks at McCann or elsewhere would take those ideas and transmogrify them and make them a part of selling things to us. Of course, I believe that that's true. The other thing that I'll say is Coca-Cola fucking taste good.

And it's actually okay to use the tools to sell something if what you're selling provides happiness to people. And Don has always kind of ratified that in his mind. What's the pilot? People love smoking. That's what he scribbles in his notebook in the first scene of the first episode. It's not guilt-laden that Don or someone else might have come and taken some of these ideas. It's actually just pragmatic.

And when I say cynicism, I don't mean it within a negative connotation. I am an arch cynic. I just think it's a good idea to be realistic about why decisions are made. Yeah. And it's also, you know, to continue the thing we were saying before, it's the business of making television or making any kind of scripted art where you're like, I'm going to harvest emotions and scenes and people from my life. This is what novelists do.

This is what painters do. And I'm going to smooth off some edges. And I'm going to then present it in the marketplace. Can I ask you a question? Have you ever harvested Kaya and her ideas for your works? Some things are too pure. Okay. Some things are too pure.

Okay. Just checking in. But, you know, when I write my podcast expose, the devil wears Prada of this industry. Okay. Kaya will be the heroin, obviously. Is it the devil wears AirPods? What are we calling it?

Yeah, I think that's good. See, what do you mean you're on the shoulder? Look at you just creating right in front of me. Yeah, it's incredible. I really have come to appreciate and admire this ending because it does feel honest and true. I think that the misunderstanding, and in many ways the lack of complexity

in my own interrogation of it from eight years ago was misunderstanding that it's one of the central themes of the show is that none of this is a binary. Don in this episode says to Stephanie's the thing that has worked for him in his mind. And she undoes the character of Don Draper in one line where she says, I don't think that's how it works. So much of our entertainment, and we're going to talk about this in terms of the Peggy and Stan stuff, is about happy endings or fan service. This show, I think, was especially in retrospect, incredibly bold because it didn't choose. It didn't do only one.

It didn't say all of one was, one was necessarily better than the other. Even the deep happiness that Peggy is demonstrating and that the audience feels for her, the tender embraces that she gets are in her office. When she's typing at the end, she's just not alone anymore in typing. Someone is rubbing her shoulders. There's, she's still at work. There's an important contrast between Donna Peggy in the episode to me. Don and Peggy, among other characters on the show.

I think this is true for Roger. I think in many cases it's true for Joan. It's definitely true for Betty. It's repress, repress, repress. Even though this is a show about people talking, do not say exactly how you feel unless you are with someone who basically can't hurt you.

Peggy is really the only person in the series who at the end of the show says, I think I love you. And is letting go of whatever tightly held repression to find her character. Even Don, confronted by someone like Stephanie, in the most open environment in the world, has his moment of critical realization

by watching another person talk. He doesn't break down and do it. He doesn't have that. Let me just actually tell you, not just who I am and whose identity I've stolen and how many women I've heard over the years or how I abandoned my children or my career. All of the, I mean, through the seven seasons of this show,

Don has done so many crazy things. But he still never really sits down, aside from with, like, random women he's met and explain to them or Peggy who he is and what he's done and what he regrets. What does he say in this episode in his, I think it's, I know for a fact it's in two of them, I'm realizing I maybe I didn't note it whether it's in the third. But the episode's called person to person. There are three person to person telephone calls logged on the show. It's essentially Don, whether literally or figuratively saying goodbye to the three most important women in his life. life, Betty, Sally, and Peggy. And to at least two of the three, I don't know if it's said in the Sally conversation

because she ends the call because she, her friend is listening on the payphone. Some devastating thing is in the air, whether it's Betty's cancer diagnosis and the reality of that or whether it's his mental state and whether he will ever come back from California, let alone remain being a living person. There's a thickness in the air that would allow honesty. and in at least two of the three circumstances, he says, I'll see you soon. That's not true, but that's what he says. We don't actually know.

If you consider it like the guy in the member's only jacket pulling the trigger, we're never going to see these people again. So in that sense, in the world of a fictional television show, we're never going to see them. That's true. Again, it is also a reach for the safety bar of normalcy in a moment when all of a sudden it seems like the walls and doors are off. Are you looking for support in your weight management journey? Zepbound terseptitide may be able to help. Zepbound is a prescription medicine used with a reduced calorie diet and increased physical activity to help adults with obesity,

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Side effects include nausea, diarrhea, and vomiting, which can cause dehydration and worsen kidney problems. Talk to your doctor. Call 1-800-545-9979 or visit zepbounds.lily.com. Let's go through it in a little bit more chronological way, because I think that there were things in the episode that are surprising that are worth noting, but I don't want to get away from this track of like what Don is doing because I think more than anything in the rewatch, I wasn't paying close attention. I just feel really struck by the fact that and maybe it's partly because Don has always been a cipher in his own show intentionally. But I think you're right that something is different in this episode. Yes. His plot line feels in essential in a way that the others do not. They all have some sort of, whether it's, we can call it fan service or resolution, he's not only is he moving through it, he's so far away from it. He's almost literally drifting.

The penultimate episode ends with him giving his car to a version, a young version of himself, basically, and not only trying to steer, as he often does, a stranger with honesty, fully embracing the hobo code. He has a Sears bag and not even a bus ticket yet. and he's in the middle of God knows where. In this episode, it's almost as, it's very disconcerting in the opening moments. And it's very intentional, right? But, like, he's at the Bonneville Salt Flats, racing cars with people that we've never seen before,

just like almost from Central casting, like, easy riders. Yeah. Hot Rod Cool Kids, drinking... BIR out of coolers. Like, he's inventing Rachel Cushner's The Flamethrowers in real time. And it's almost like, is this a movie? What are we doing with this episode? And I think this is intentional.

Winder is a student of television. I'm like, are we going to reveal that this was all performance, that there was something else going on here? Is this time passed? He's trying to unnerve us. For sure. And make us uncomfortable. And I think the thing that becomes clear later is that he is testing the limits of escape

in any way possible, get as far away as he can, as fast as he can, the advice that he keeps trying to give people until it's finally thrown back in his face. But literally, this is the first time. For a show about someone who we, the central question of bad men is who is this guy. Yeah. This is the first time an episode began where I was like, no, seriously, wait, who is this guy? So, Don is about 42, 43 in this episode. Yeah.

That's right in between where you and I are, I believe. I mean, let's not make a federal case out of it, but yeah. And, you know, like, let's be very, very direct. Don is having a midlife crisis. You could make the case that can- Because people have shorter lives then, right? Because I'm not having that yet. Please continue.

No comments on your personal health. I think that it's very clear that obviously you could make the case that the entirety of the series has been life crisis. But I think particularly in this season, especially when he abandons McCann, that is a moment that I think many men and women experience in the world where they're sort of like I've fucking had enough. Like I don't want to do this job anymore. I can't be forced to have these responsibilities. I need to go wander. And in the service of the TV show, sorry to interrupt you, I do think that this was a major.

element of discomfort for the viewer because the assumption of television is that everything reverts to the mean and everyone comes back to home base. This is a show that famously emptied its writer's room board every year. So multiple season finale could have been series finale, especially

season six at the abandoned house with Don and the kids. This was a show that was incredible at season finalies. Amazing. Because I think he was like, that's all I got every year and started over, like Louis C.K. with his stand-up acts. Can we still reference that? So, yeah, sure. It happened. And it was happening in 2015.

Yes. Him leaving New York and leaving what we thought the show was profoundly, not like going on a walkabout in Palm Springs like he would do every 16 months, was very discomforting. And all of a sudden, we've run out of road, just like he did. He's not coming back. Yeah. What a wild thing. And I think Winer was telling us something and prepping us for where this episode was, but I don't think I was seeing that in real time. It did feel like this season was not a part of the long-term plan. And I often judge shows that don't feel, you know, I'm quite hard on lost as a show,

even though I basically loved it and watched every moment, you know, wrapped. I also, by the time we got to the end, as many people did, I think we're sort of like, God, they just like kind of backpedaled their way right into something like this, huh? Jeez, that wasn't what I wanted. This show, I feel like in many ways did the same thing, where he just, maybe he had some loose ideas about where he wanted these characters to land. But in particular, you can feel the kind of like, sorting out like, well, what if this happened?

And what if this happened? Other episodes don't feel like that. This was one of the most watertight shows ever. Every episode was a diamond. And so when something like this happens in the show and we go to the Salt Flats and we meet these new characters that right at the beginning of what we're led to believe, if you're a huge fan of the show, is such a critical moment.

And we're like, what the hell, man? There's 55 minutes left of Mad Men. Why isn't Don talking to Roger right now? That's what I want. Why isn't he talking to Peggy? That's what I want. Roger and Don will never talk again. Crazy. Crazy. Wild.

It leaves me sad, but they do have that incredible moment earlier in the season in the bar together that is very, very special when he reveals that he's been dating Marie Calvay. And, you know, that's really the last beautiful moment between the two of them. But yeah, I think he did this on purpose, and I understand why he did it. And I think he's trying to set us up for, he's trying to make us think that there are no happy endings when, in fact, he's about to give us a bunch of happy endings. We also then get, and we could talk about, like maybe before we return to Don, it's worth saying, like, Roger Sterling, Hall of Fame television character.

I don't know in practice if there are any characters I miss more weekly. Maybe Ron Swanson, we're talking about good mustaches division. I would take Roger over Ron like 100 out of 100 times. I love Ron Swanson, but it's not close. I think just even getting the little taste of him again, you know, swirling it, like vermouth in the glass. Like, what a combination of an actor filled with joy to do this, but somehow that not overwhelming the acting piece of it.

He's a lived-in person who has gone on a journey that everything he does is effortless. Yeah, and he's a person not without pain and bad situations. Oh, I mean the performance is effortless. The man himself has now become complicated and rich. He feels like he's kind of gliding through the story, but at the same time, it's like marriages are falling apart constantly. He's going through his own kind of crises. Professionally, he's made forever because he basically comes from wealth

and will always have wealth. But that doesn't mean that your daughter won't run off to join a commune, which is basically what happens in this season, you know, and that he has no answer for how to get her to come back into his life and into what he perceives to be the real world. He kind of flees too, and he flees into the arms of this French-Canadian woman. Great scenes, though. Yeah, even Julia Ormond are wonderful together.

Great scenes. When he orders a bottle of champagne for his mother. Or when he just says, he says that would be. yell at me slower. All I got was suitcase. It's French is decent. It's phenomenal. Well, it suggests that some time has passed. Yeah, yeah. He's been learning. Yeah, he's been boulevardiering around Montreal.

We also get our first... Is this the first appearance of cocaine on Mad Men? I believe so. Tell me what you think about the Joan arc here with her union with Bruce Greenwood. Well, it's not a strong union. It falls apart. It felt like it was going to be until this. episode. This is kind of...

That happens very fast. It happens very fast. Earlier in the season, they indicate that there is a tenuousness because you've got two people at different stages of their life. Joan is ready to be a person in power and control. She has gained the confidence that she needs after being stepped on for men to climb over the course of her career and that, is it Richard? Is that her boyfriend's name?

I believe so. He's maybe 15, 20 years older than her, already built his own. business. He doesn't want to do this anymore. They've kind of suggested it, but when we get to this episode, we think that they figured it out, that they're going to be together. Then Joan gets his hairbrain scheme to be a producer? Yes, like an independent producer of corporate content. Right. Which I guess in many ways is a very lucrative job that exists right now. It's brilliant. She's

well ahead of her time. Thanks to Ken Cosgrove. I think truly, I mean, the degree to which like, it's no wonder that people, a lot of people watch Mad Men during COVID because like every good thing in life comes from dinners with martini, apparently, and from people you know, IRL. It's really a stern rebuke to Zoom culture.

That show is, yeah, this is the ultimate who you know show, because most opportunity unfurals because we had a cocktail together. I think one of the great things, debates about fineries can often be reduced to, do you earn the contrivance of the plot by the emotional payout for the character? And it's often incredibly hard

to build the scaffolding to end in just the right place for those to be in harmony with each other. I think that for Joan, the character, as you said, this makes sense. She loves working, as she says to Roger, within this

episode, she makes a reference to people getting the timing right. And that has been an unfortunate part of her life. Her ending up with her kid set for life, building this business with both of her names, instead of taking on someone else's name. It's a lovely detail. It allowed us for the Peggy friendship thing to be real, but also not definitive for either of them. I hope that her business is not torn asunder by cocaine. Well, right. She did.

She seemed to enjoy it. She seemed to really enjoy it, which is weird because most people don't. Crazy. Historically. Well, I love her description of the sensation. It feels like I just got some very good news. I mean, is there a better piece of writing about the act of using cocaine? For the first time.

For the first time. I think that's crucial. Also, you know, they do an extraordinarily small amount. Yes. Yes. Which is probably also bodes well for their future. It's being treated like it's, you know, an ancient golden dust delivered directly from a temple in Venezuela. Is it not?

I mean, in some ways it is. Not anymore. Yeah. No. Listen. No, it's been stepped on now. It's way too many times. I think that the Jones story and the Peggy.

story, which I want to talk about the Peggy story less in terms of work because that one ends up being more about life. Circling back to a point you made about the show's essential message about people and whether they can change. I think there's an argument to be made that Madman never really takes too strong of a stance on the idea that people can change. People can change behavior. They can change their relationship to their past or to others, but they themselves don't change. They're just often in denial about who they are. What changes in what this show profoundly was about, and I think even an episode was called this, is time and life. So people don't change, but context changes. I believe it was the third to last episode. It was called Time and Life. There it is.

And I think that one of my favorite, favorite moments in the series is when, Mrs. Blankenship, the secretary who dies and Bert Cooper eulogizes her. She was an astronaut. She was an astronaut. And that's a relevant line for many reasons, one of which is Bert Cooper's death episode is the episode when men walk on the moon. People refer to it on draper's looking like an astronaut constantly. But in Burke Cooper's construction of it, Mrs. Blankenship was born like in a barn in a different, essentially a different century, maybe actually in a different century. I don't remember her actual age. I believe that was the case. And died on the top of a skyscraper. She was an astronaut. The finale is proving the idea that all of these people were astronauts. And in fact,

Maybe we all are astronauts because we are moving through time and life at riotous speeds. Think about when we first see Don at the Bonneville Speedway, they're breaking the speed of sound. They're breaking records. And so bringing this all back to Joan is when we meet Joan who she is and how she carries herself and how the world treats her. Actually, let me rephrase that. She always carries herself exactly the same. The world of which she is moving through in that way changes. And she may not have gotten the timing right with Roger, but she has gotten her own timing right at the end in a way that I think is profound. There's something really interesting about the way that she's portrayed in this season in particular. And I just revisited the whole season, which is that the advances that come her way continue throughout,

despite the fact that the culture is evolving here. We're seeing a move from the mid-60s to the late 60s. There are still basically men in rooms saying, like, we're getting a drink tonight and you're going to sleep with me so that I'll give you business. And that is not true for many of the people in this show. We're literally seeing an evolution in our culture. but Joan is still an absolute object of desire even through the eyes of the makers of this show. Like they are using her as a vector for desire all the time.

So she has to have more will and more grit than pretty much any character. I think the show does well by her in that respect. Like I really think that they let her, and I mentioned this to you before we started doing this yesterday, that I think that through the course of this show, Christina Hendricks, becomes such a great actor. Like you can watch it happening.

across seasons. And she is one of not quite my favorite part of this final season, but she is among my favorite storylines, what she's given to do, how she changes a decision she makes. And she's always crossing paths with people in such interesting ways. Her relationship to Don, to

Roger, to Peggy, these are critical relationships that the show couldn't survive without. And like all great long-running shows, Mad Men gave its players opportunities to be great opportunities on the field, and some of them just are great, like Elizabeth Moss, and Some of them rose to moments like January Jones,

but I think the development of Christina Hendrix and her performance is really amazing. I also think it's worth thinking of that question of breaking speed records and time and life and missing your moment with the other prominent women characters on the show, especially as demonstrated in this episode. Peggy is probably only a few years younger than Joan, but by the quirk of her birth and arrival

on the stage of the show and of the world, she's benefiting in a different way, just slightly on pace with the culture to a different degree. Now, has she traveled as far as anyone else or maybe further, considering the way we met her? Sure, but she's on a track in a different way that she is aligned with, like when Pete is like, you'll be the creative director in 1980. And she's like, that's far away, but he's like, well, that's the arc of time,

and you're like, this is where you're in sync with it. And I think about it, too, in terms of Sally Draper, who becomes one of the more compelling characters, I think, over the course of the show and also the focus of a lot of potential spin-offs that you and I keep trying to create.

When will they give it to me? I mean, the one with her like in downtown 81 in like Warhol and Baskiaz, New York, it's so there. I find her role

really fascinating. And speaking of losing time, we haven't even talked about Betty, about Betty, but I think they're, they're twinned, I think in many ways,

you know, that Sally is beginning to live so that, and Betty has to die. Like that feels like a very purposeful move on their part. The season is complicated because there's an attempt to evolve the Sally character to become more of a woman, which is really hard on a young actor. And Kieran and Shibka, it's interesting.

She really has gone on to become arguably the most successful actor out of this show that is not John Hamm. Well, you know, I ride for Jay Ferguson for other reasons. I mean, God bless Stan. I love him. You know, Elizabeth Moss is a sainted performer. but in many ways she was like already on an upward trajectory when she got to the show because of her success as a child actor. Yes. Kiernan Shepka we'd never seen before.

She is like in very successful streaming horror movies in 2023. Like she's got a real career. You can still feel her figuring it out. Yes. As a performer, which is a bit of a strain on a show that is otherwise kind of impeccably performed. I agree. So we don't see it as much. She's quite good in this episode.

I'm not trying to criticize a teenager. But I always find it hard to get my head around. the evolution of that character because they're asking her to do a lot as a performer. And they're asking her to not only do a lot scene to scene, but to embody traits of both of her parents' actors' performances. So hard. And we are told more than we are shown

that she is truly Dick Whitman's daughter in a different way, and we see Don respond to that. But I also think there is some interesting stuff to be unpacked about how we leave her. And again, I keep referring, Sometimes there's the finale, and there's like where we left right before the finale. And so much of the milk and honey root is about Betty and the diagnosis

and her response to the diagnosis, and she doesn't want Sally to know. And Henry goes to tell Sally. And he's like, he says, he tells her, and she covers her ears. And it's an incredibly intuitive performance and a great directorial choice. And he says, it's okay to cry, sweetheart. And then he breaks down. And she has to comfort him.

And the deep message of the show, for people of Winer's generation and beyond this, but particularly the baby boomer generation is that they had to parent their parents. Yes. I would argue that baby boomers themselves haven't done the best job of being grown-ups themselves, but maybe every generation gets to litigate that.

Yeah, I'm thinking about it a lot because I raise a two-year-old. Exactly. But the idea that she is, Betty says to her in the penultimate episode, in a very Betty way, like, here's how I want my hair to look in the coffin And then the last line is like, I used to have to worry about you and now I realize I don't, your life will be an adventure. It is incredibly moving.

Yeah. But at the end of the series, Betty's smoking in that kitchen still. And instead of a maid, Sally is doing the dishes. And what that says about her wings and whether they are clipped by this or whether they are not is heavy. It's heavy to think about, you know. Is progress in the Obama model? Like, is it a slow but inevitable arc? is it really a matter of circumstance, luck, and timing,

whether you get to, especially living as a woman, whether you get to break through in any way? I think it's reasonable to assume that Sally, who witnessed the end of her parents' marriage, was scandalized by her child, or by her father, as Don points out, and will experience the death of her mother all before turning 21. You know, it's going to have a complicated life.

She's going to have a lot of pain, and she's going to act out. And so that's one of the reasons why that's a great idea for a show. Yeah. It's because you know that she's emotionally complex. very smart and a profound blend of defiance and creativity because that is kind of what Betty and Don are. You know, Betty and Don are the most beautiful people in the room and they seduce everyone, but they also have like these major storms inside them. I think she's a really good character.

The Betty character is incredible to me. Like she retains the first half of the 20th century point of view for the show. She really is a woman of the 20s, 30s, and 40s. She doesn't move. And she won't reveal her weakness. Her head increasingly becomes like a helmet, her hair. She's like starting to resemble like the bride of Frankenstein with the way her hair is styled by the end.

She thinks it's such an interesting choice. And she goes through this complicated change throughout this entire season too, where she and Henry are kind of at war over whether or not she's allowed to have opinions about things at parties. And then she wants to go back to school and kind of rediscover her intellect and her reason for being and then just as she's kind of figuring things out it's taken from her right and this happens i mean this is this happens to people in life so you know january jones another person who i'm like where is she like what like she you would not think it because she's presented as a model in the series she's strikingly beautiful but also someone who really had a handle on this character by the

end of this show yeah and i really am like quite moved by the end of this this particular part of the story so i think i thought it was really well handled and it's not what i think the episode was often dinged for, which is like, and then everything's fine, you know, which like is true for Joan, who's a powerful businesswoman who will have Rogers money for Kevin or, you know, other characters will talk about, you know, as we go on here. It's a real tragedy what happens to her. I mean, is she 39 years old? I mean, how old is she? Barely, if anything, and it's over. And when she's, you know, continues to going to school and Henry says, like, what are you doing that for? And she said, what was I ever doing it for? Right.

What is the purpose of doing? I mean, you know, tossed away line, I don't know, I'm losing track. I think that's actually in the previous episode, but that's just sort of a devastating statement of a worldview, which is actually what's the point of any of this, when we consider the proscenium arch of our life? How much do we actually get to be on stage? Yeah, that resonates with me for sure.

I also really appreciated on this viewing of some episodes, but particularly the finale, something that has fallen out of favor, or at least the complexity of this has fallen out of favor, which is the willingness of the show to let its beloved characters be shitheads, be dirtbags, be wrong, be obstacles to people that they and we love over the arc of time in a way that isn't shooting each other. It's not the same language of the bad actor, not bad actor,

but in performance, but in the sense that the contemporary shows that Mad Men is often compared to and considered with in terms of the depth of character development over time, it is different than Breaking Bad, it is different than the wire, it is different that the Sopranos that no one whacked each other. Lane wax himself. Yep. Kenny loses an eye and that one guy loses a couple toes.

Yep. But you mean the lawnmower guy? The lawnmower guy. Yeah, that was a tough one. It's funny that you say that though, because the other thing that I noticed in this episode is that there's not even really like metaphorical deaths.

The show is like incredible at people cutting each other down to size constantly. The barbs, the, you know, Roger Sterling asides. There's, people are melting each other all the time on the show. And this episode's not really like that. It's much more melancholy.

It's much more about, it is about endings. It is about realizing the stage of your life that you're in. It isn't a quip fest like so many good episodes were. It's also about boundaries in a way, because if you are quipping, if you are insulting, if you are hating, you are connected to a degree that where you are loving. And one of the things this episode does really well, and I think it is in many ways then the opposite of another show

that we're doing on this series, The Office, is that when Peggy and Pete and, my God, Rich Summer, who only eats a cookie in this episode, thank you, Harry, Harry, Crane, they're going to meet for lunch. And she's like, what are we doing? We've never had lunch together. Like, we know each other and we have complicated history,

but we're not. What? You know, in the degree that when Roger doesn't see Don again, okay, there are other people in Roger's life. It's a very important restatement, I think, of what actually matters. Yeah, I am fascinated. to explore this very personal thing with you,

but I don't want to like overextend my thoughts on it. But this aired one week after Bill Simmons left ESPN when we were working together. Yeah. Eight days, I think. Eight days. And that was a very fragile time. I think in our professional lives, certainly in mine.

Whether or not, like what it meant to be bonded to people at work is always being tested. You and I have been lucky enough to work with close friends over the years. We are close friends. For a show like this to be reckoning with endings, like really when a flag went up about the future of the place where we were working that we had a lot of emotional investment

in, I know many people thought of Graham was sort of like, finally, there is a place where I can do the things I want to do. And it's not easy, it's actually a pain in the ass, but I can feel very proud and good of what it is that we're doing. And you see that theme over and over again in the show. You see with SDP, like, when they build their new firm and they think it's going to be perfect,

and then we watch it get dissolved, and we watch it get it absorbed. And, like, there were a lot. I saw a lot of echoes in my own life, and I see them again as I rewatch the show about the way that you think you've gotten somewhere. It's going to be what you're going to do for the rest of your life.

And then after five years, you're like, I'm really tired of this, or there's a new boss or something happened. And now we have to figure out what we're going to do next. And this is, this energy is in the Peggy Joan Bloody Mary breakfast where you realize, the repetition of some things on the show isn't a bug, it's a feature, which is to say that the new thing is always the next thing.

There's always an opportunity to be excited, which is maybe all we ever want out of life. You just want to know there's a next thing, and you want to be able to continue to push your excitement forward. Yeah, not everyone is like this, but I do find that people, like, in our lines of work are like this. Or maybe it's not Rosie. Maybe there's something psychologically broken in us

that we keep throwing the bridle onto a prettier pony, No doubt. I'm fucked up. That's why I'm like, am I happy? Am I actually happy? Like, I'm fucking, I should be so happy. I have the best life ever. Why am I not happy? You were 11 minutes in that chair before you were like, so my dad. Exactly, of course. It got real, real. But why not? Like, what else am I doing? I agree. I'm a student of madman. To an extend the analogy of when Bill went to Esselon, what was left behind. Did he, did he in the lotus position dream of the ringer? You tell me. I hadn't moved to California yet. of which California on the show

figures so weirdly large that I think one of the challenges that I had to this season in this episode and to many did was this idea that everything that felt really good because there's so much forward momentum that feels good in the show. Like that episode was shut the door,

have a seat where they form a new firm in the moment in a hotel room was that there was always going to be something new, new, new, and it was going to be exciting and that's also, I realize I'm talking about advertising. It was this episode and this season was about pulling the rug out. These relationships are not forever. Your life is not forever.

Your passion might not be your destiny, et cetera, et cetera. What you're left with is yourself. Maybe this is as good a time as any to steer into that. I want to talk about the Don part because it's a show about Don. What happens with Don is the message of this finale and the one that I think I was pretty blind to in a lot of ways. before we do that, we just got to do

quick Joaquin Phoenix Gladiator up or down on Peggy and Stan because I even becoming friends with Jay Ferguson and working with him have said to his face

that I didn't buy it and now I don't think I was right. Yeah, I completely disagree with I was crying watching it this time around. I was crying watching it this time around like this isn't just magical

kind of this is actually like this feels like a movie. This is movie writing. It is there is a fantasy element to it. Of course, I recognize that, but I am so in the bag for those characters. We've now spent many seasons of them

building towards that. This is not, to me it wasn't like, wait, what happened? They were confidants for each other for many years on this show. And neither of them could really fit. I was remember watching episodes of season seven and looking at Elizabeth Moss's character in her

sad little apartment in the building that she bought. And I'm like, why is this person single. You can't really make sense of it because she's very smart. She's attractive. She's successful. You know, she's got a great wit. She's fun.

She is fun. And the same as Stan. You know, Stan, he has that fast, I don't remember if you remember the Mimi Rogers episode where she comes in as like a photographer. Oh, yeah. And she kind of seduces him and then she attempts to seduce Peggy. And that is almost like a hint at where things are going. It's like she was going to be like the connector.

And their thruple hints somehow. but I really, really loved it. And I think it's like basically the best episodes of Mad Men feel like a great... The show feels like a 700-minute Billy Wilder movie to me. And that was like a pure Billy Wilder moment. And to put my own cards on the table, why was I so obstinate about happiness and pleasure? Where were you then?

Where are you now? I think that's really the question. And first and foremost, it is impeccably staged. And her performance is outrageous. It is God tier. Though camera is holding on her for long stretches. And it's so funny that he says he loves her and she says, what? And then in real time, she pitches herself on this campaign.

And there's nothing cynical about it because she says, I mean, I don't even think about you. I mean, I do all the time because you're there. And then she says, and you're here. And she touches her heart, and I'm going to choke up on this podcast. Yeah. Well, they've been married for a long time and did not realize it. Yes, because none of them actually know what love is, because it's been modeled for none of them.

Right. And they've lived in this cessable, what is, what does Lane call Pete before he punches him in the nose? A grimy little pimp. That is the world that they've lived in. Yeah. And it is twinned in a weird way. Pete and Peggy are always twin, but Pete spends, and I didn't realize it in the moment either, his nastiness is, he is spinning in unhappiness, and Don calls him out on this repeatedly for not notice, and it's funny, and it's rich from Don. But Pete doesn't appreciate anything that he has, and he's never satisfied and he's never happy. And he turns around in the end and it's like, wait, I just was, my dad didn't do this, I didn't understand it. I could be happy. And he allowed. himself that possibility, and then Peggy does too.

And I want to put on the record of Mia Colpa, I was wrong about this. I was 100% wrong. I am a little bit less pro on the way that Pete's story resolves. That to me feels the most like this week on the loveboat. Like Pete gets a job with Learjet.

If we were going to psychoanalyze, we are not. I think the presentation of a complicated man choosing and believing in the happiness and sanctity of home and hearth and flying off literally into the middle of the country no into dorothy's home yes into odds that may be a projection but maybe it's a relatable projection i don't know i think it's

interesting because pete is often a very self-aware character and his his evolution through the show i really like and i like how he basically realizes that that don in many ways is his kind of the way that roger has always felt like Don was his deliverer of greatness. Pete figures that out too. Pete, even though they resent each other at times, they hate each other at times, they're always quarreling. Pete throughout season seven is like, Don's the man. If Don does it, we're good. Yeah, I trust him completely. Yes. And I love that they get to that place. The same way I love, I think it's a bit unlikely, but the way that Pete and Peggy figure out a kind of harmony together, it's respectful. Despite what has transpired between them. They get to Burger Chef. Yes.

And that is really nice. Pete getting out of the luxury car, clutching his beautiful young daughter and carrying her onto a private jet with his ex-wife soon-to-be new wife. It feels a little phony to me, but I wasn't taken out of the show. It also, you could be read in a different way,

which is that on Mad Men, only two places exist, New York and Los Angeles. I certainly don't relate to that in my own life. Pete's basically flying to the moon. He's gone. Yeah. He's from Greenwich. He's not even relevant anymore because he's gone to a different place.

And so will he and Trudy be happier taking a Learjet to, I guess, Milwaukee sometimes? Maybe. But it's no longer the business of the show to be concerned with it. It seems unlikely it does, but it does feel like an adequate realization of something that you hear from a lot of dissatisfied people in their approaching middle age. We're sort of like, can I just get out of the rat race of my life and just go somewhere where everything's a little slower? Do you remember that when you moved out of New York a little younger than I did, but like there was 30. Okay, so there was, and you didn't have kids yet, but the one of the things that moved us out of New York, there was the podcasting, the podcasting was here. You got to go to where the actions.

Truly. Also, it would make a change in life. This is where the TV industry is, et cetera, et cetera. But a not insignificant factor was that every gathering of like-minded peers with children was just about where they all thought about moving and dreaming. It was so boring to only talk about like, well, Maplewood is not, or maybe Austin could be kept weird. It was just like, you know what, fuck it, let's just go. Because I would rather go than have this conversation.

I cannot even fathom having a child in New York City. So I applaud you for you. One, great. Two, that's pushing it. Seems crazy. Let's get to Don. One larger question leading into it. Why the phone?

Why is everything? I mean, this breaks all rules of filmed entertainment. That these goodbyes, these scenes. Stan runs to her, thank God. but otherwise, they're all on the phone. Can I circle back to my dad? I would love to. Should we call?

I'll call him tonight. I love my father. My parents were divorced, and so my dad made an honest effort to stay connected to me and my siblings, and he called us every day, which sounds nice. And when I was 15, I was like, this is heinous that we have to have a 32-minute conversation every day.

I have so many things to do, including not talk to you. And I came to hate talking on the phone because I spent so much time on the phone as a kid. To this day, I do not like to have long phone conversations. Our friend Chris Ryan can attest to that. But it's easy to forget that this was the only way to talk to people. In 1969, if someone was across the country, we actually see earlier, I don't remember if it's in this episode or the previous episode,

one of the creative members of Sterling Cooper-Draper Price that didn't come along to McCann sticks around to make long-distance phone calls because he doesn't want to have to pay for them at his own home. you have to, there's a practical reason for this. Side note, when I was an intern at Matador Records in 1998, that's what Cat Power did also. She just came to the office to make long-us and phone calls. I mean, shout out to her.

I've been trying to make a connection with her for years. If she wants to call me, I will happily collect that call. I think that it's the only thing that makes sense for Don in particular, though, to get back to those three women that you talked about. And it also is kind of like a wonderful contrivance in the Peggy and Stan story. It works. It's interesting, you know, the rule of threes. He talks with three women.

I think it's also you could read into, and I'm sure grad students who've written about this show have, that it suggests that there always was a gulf between them. And there's always a gulf between people, except in the Leonard moment. So let's talk about where Don ends up. He runs out of road, literally.

He runs out of everything. He runs back to the person who he believes knows him best only because she knows he's a fraud. He spent the previous episodes kind of confirming or kind of slightly evading the fraudulence again and again, including with the veterans in the previous episode.

He's a wreck. He is, of all the times he's been red-faced and sweaty and drunk, this may be the worst, because he says, do you have any liquor? I've been drinking beer all night. It's a beyond hair of the dog. That's rough. The whole dog.

Stephanie, whose own life is in a bit of a shambles, says she's going to Esselin. He goes with her. In the previous episode, he actually attempts to retrieve Diana, the waitress from earlier in this season, who is a mysterious, depressed woman who has fled her family,

and he seeks safe harbor with her. And this is something he does throughout the series. He seeks solace in broken women. Yep. And impossible relationships. Earlier in the season, Rachel Katz dies,

and she wants him. All these things are happening where these women are falling away. Betty is dying. Megan is gone. In fact, she does not want to reconcile and wants to stay in Los Angeles this season. Everyone is abandoning him.

And so he returns to Stefan. as this last strand of connectivity to Dick Whitman, Anna Draper, this world before all of this. And so that, I think, is the reason why he goes there. Like, I love that as a storytelling choice because he's got nowhere else to go. And historically, over seven seasons, women of various intimacy have fixed him temporarily.

And he runs out of that, like he runs out of road. All of this builds toward, she leaves him in this episode as well. says, I don't think you're right about this idea of always moving forward. He gives her the Peggy speech that he gave Peggy in season one, basically. You will forget this. You will be better than this. She says, I don't think that's how it works. There are consequences.

Also, important that might not be as easy for a woman to skate away from your family in the way that he has in this society. All of this builds towards the Leonard scene. Now, at the time, I was, I will say, probably I was in therapy, but not listening as much, not paying attention, not integrating. I was resentful of time spent away from the people we love, what we don't get Roger and we said we get this. And I didn't understand that what we had reached, I think,

was a kind of like, we'd sort of elevated out of the television show economy. We were no longer moving action figures around the game board of Manhattan. And now we were getting the raw uncut. The artifice was away. Weiner basically opened a vein. And he was like, this is what this is about for me. the creator of the show. It is about how we do not recognize love when we get it.

We feel lonely in our lives surrounded by the people that matter to us, and our greatest fear is to be left alone in the dark. That is what this show builds toward, is towards a stranger saying this and weeping. It isn't the conclusion, though. Correct. So I think that you're right that they are, he has put his finger on the ultimate pain that is driving,

the creation of all these characters and their stories. He's also made an amazing choice to put it in the voice of someone who've never seen before. Or if you've not watched network television, maybe never seen before. And let Don respond to it. And this is the actor Evan Arnold, we'll say again, get him credit.

Let Don not say anything. One of the great talkers, one of the great presenters of stories. That's what he's been valorized as throughout this entire show. Instead, let some other guy do it, some weird guy. And we get this long, deep focus on this man, but we don't know,

talking about a pain that millions of people feel. And he's pathetic, and it's lame, and it's also true and crushing and irrefutable. You know, there's just, that's like it's the human condition. I think it's particularly the human condition for men in their 40s, but nevertheless,

I do think it's the human condition through and through. We're lonely, we're lost. No matter how much love someone gives you, it's never enough. I don't Don has a moment But Don always has a moment He was looking for a moment Just like you said

The same with those women Gave him a moment He was just looking for a moment And one of the reasons Why I'm a little cynical about the ending Is because he just needed One more catharsis to get to the next step To get back on track

That is what I think happened there I don't know if I thought that when I first saw the show But this time around I'm like He kind of needed to get something out of him He needed to exercise something Yes And that Evan Arnold did it for him Yeah, I mean, I think that that's also the difference between like everything with like art and life.

This is a reference that I know you're going to get because you're a bigger fan than I am. But like Albert Brooks been doing the press rounds recently, this is a giveaway as to when we're recording this. But he was on Mark Maron's podcast. I haven't read this yet. Well, I won't give anything away, but he talks about the movie that I love. I know you love too, defending your life, which is essentially about in the afterlife, you have to give up the fear that dominated your life. And he says to Mark Merrin, like, I made that movie. and I think about how I made that movie

every time I'm still scared. There is no ending to this cycle of it's not enough, it's not enough, my God, it's my fault. No ending to that cycle. For the purposes of an hour of television, I appreciate now in a way that I didn't before.

Don doesn't hug Betty. He doesn't hug Sally. He doesn't hug Peggy. He hugs this stranger and cries with him. He has a person-to-person moment. He is given that gift. He is present for him. that gift. The deeper message that I'm wrestling with because I think it's true in this episode

and is done, I thought it was ham-handedly, now I think it's done brilliantly, is that we don't get to end with any one successful moment. We don't get to have that emotional catharsis ever. Maybe you do in a TV show. And if it had ended with him on the cliff, he's frozen forever the way Tony's forever put it, Tony Supranos putting an onion ring in his mouth. If you do not believe that Don returns to McCann, what does he do? I can't believe I'm doing this, but I am fan of the Sopranos finale, new critic,

he doesn't exist. He doesn't do anything. He's a fictional character who does not exist. So funny, with movies, I absolutely think that way. I do not scheme out

what happens next, but with TV, I always think about it because it's a longer relationship with a character. It's built for you to have that parisocial relationship and care.

So you think he goes back to McCann. I'm not good at very many things. I've gotten good at this what we're doing right now, or at least good enough. And I think if someone were like, if I had a crisis and I was like, I got to give all this up,

would I want to come back to it, I probably would. He's better at that than I am at this. And the idea of obfuscating it, he doesn't want to be Ken Cosgrove and have stories published in the Atlantic. Maybe he wants to be Francis Veracopola. We get the implication over time

that he's a sinist. But I think he really wants to do what he's best at. He really does like that. He doesn't like being a cog in a machine. That's what we saw at McCann. We saw at McCann that he left because he did not want to be one of 30 men in a room. He wanted to be the man in the room.

I think he will find another way to do that. He has imposter syndrome to a degree. I mean, everyone does. But it's maybe the greatest long-form presentation of imposter syndrome ever, both because he is an imposter. He's Dick Whitman, but also because of the way he operates in the world. And I think that one of the keys to his success, and it's key to every...

You alluded to this earlier about everything's a scheme. There's an episode where they teach Lane how to do a meeting. and Rogers like, this is this, you don't drink, you do this, it's all a dance, it's all scripted. That Don believes he is a fraud and he has found his calling in an industry of fraudulence. I think what he has reached at the end is where Winer claims to be himself in the interview I was referring to where he's like, the Coke ad is beautiful. It is a beautiful thing. You can do a deeper dive into it and talk about, you know, capitalism or whatever, but it is a beautiful expression of an ideal and I am not cynical about that. And so I think that that is where the show leaves us too.

I think that maybe Don is open to the totality of himself, flaws and positives, and has synchronized them into something that for the sake of the show, in a brilliant stroke for the show, is expressed to us in this ad that did that also. The ad, Don didn't make the ad. Don is the ad. Aha. That's the ending. You sure you don't want to send the pod right there? I kind of do.

Yeah. I do want to ask you, and the one, the one, the, The one thing we do in this remarkably free-form exercise, I'm glad we got Chia-caffeinated before we started. When Bill first pitched the podcast, he determined he's good at Lists. I don't know if you've ever worked with him, but he's very good at that. It's an inspiration to me every day. He said in his mind there are five ways shows end, and so far it's kind of proved to be true.

And here are the five. We always do this. Number one, they landed the plane. Number two, they took a big swing and it was super fucking polarizing. Number three, they fucked it up. Number four, this is unedited. This is from his text, by the way. Four, they limped to the finish line.

Five, it didn't seem like they landed the plane, but in retrospect, maybe they did. So I suspect that the last option is where you are living. That's where I'm at. I think that we're missing some nuance in those five options, which is frankly my job here at the ringers to tell Bill when he has a very clear idea. Hey, are we sure there's not a sixth option? Is it possible to limp a plane to the finish line on a tarmac? Sully would say yes. He doesn't even need the tarmac.

Yeah. Was this an emergency water landing of a season finale, series finale? I think that it's a deeply melancholy and strange, but also uplifting and cheery and fun and also co-caddled and doom-like and also cynical and also joyful conclusion. So the show was a lot of those things. It's hard to know how it fits into this new, metric because I don't think it's a perfect finale, even though I think it's a perfect show.

I think I agree with you, but I also think, and this is one of the benefits of doing this podcast and these conversations with time, this finale is the show. It is not, in that it is rich, it is a rich text full of ambition, ideas, brilliance, heart, and just trying. know, and trying things. And I think that it is representative of the show, even though it's its own, where it sort of, it left Manhattan, it left Earth in a lot of ways. It is, it's not the show was at the beginning in terms of where people are, but in terms of what its project was, I think it stayed true. And I don't think I thought that eight years ago. I think I've made this joke before. So if anyone's heard me say it, I apologize. But I have always thought it would be

very funny for my tombstone to say he tried. And I feel like Don and Winer. and Peggy and Joan and Betty and all these people. They tried. Do you know what my favorite moment was really in this episode? When I was thinking about is when Don has hung up on Peggy and he's collapsed. And he has reached the end of everything and even the ends of his fiction of himself. And Supergirl comes over. Shout at Helen Slater.

Helen Slater. And she's basically like, she doesn't say this, but she invites him to walk with her to her thing. We meet Leonard. You always can get up. you always can keep going. You always can show up. It might not be under ideal circumstances. It might not be in your heart.

You may be faking until you make it. But that is one of the most central tenets of therapy as I've understood it. And I think that that it's as true for men in their 40s, as it is for seven seasons of a television show. You can always keep going and see where you end up. Unless you're Betty Draper. Unfortunately for Betty Draper.

Unless you are an interesting wife character during the first golden age of television, in which case, you can't. And you can be reviled for many years, for reasons that are still mysterious to me. What a downer way to end it. Truly, what a pleasure to talk about,

what is the most talk-aboutable show maybe in the history of the medium. You've opened Pandora's box here to future conversations of Mad Men. I mean, Mad Men is the, this is the rich text. There is, Sean, there is no person that this person would rather have done this phone call with. Thanks for being here. Thanks for being a person, Andy.

This episode of Stick the Landing was produced by Kaya McMullen and Kai Grady, and our theme music was composed by my good friend Giancarlo Volcano.