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‘Mad Men’ Postmortem: Director Michael Uppendahl On Don’s Many Women

Spoiler alert: Do not read unless you’ve watched “Mad Men” episode 709, titled “New Business.” 

The second episode of “Mad Men’s” final season saw Don cross paths with several women in his life, starting with his first ex-wife, Betty; his soon-to-be-second ex-wife, Megan; his ex-flame, Sylvia Rosen; and the latest object of his affections, the waitress from the diner in last week’s episode, Diana. The episode’s director, Michael Uppendahl, discussed with Variety what all these close encounters mean for the tortured ad man.

For an episode titled “New Business,” it felt a lot more like old business.

(Creator) Matt Weiner found an interesting way to bring Don’s old flames back onto the screen. It allowed the viewers to reconsider those past relationships.

Let’s start with Diana, the waitress. 

She’s a cryptic fascination for Don and the audience. Especially in comparison to the other women, particularly when she’s in the elevator and they see Sylvia (Linda Cardellini) with her husband. I was really happy with that scene. They look somewhat similar, and of course it’s awkward for everyone involved, except for (Sylvia’s husband) Arnold who’s drunk. It’s the idea of how many women he’s had in the elevator. And these two particular women are different.

It’s telling even in just what the two women were wearing.

Exactly. Elizabeth (Reaser) did a great job of being somewhat embarrassed by wearing her waitress outfit. But she’s obviously done this to herself in a willful fashion to reduce her life to this, so you can see her trying to be proud of it but also trying to look pretty good. And meanwhile Arnold’s bloated with booze. He’s an interesting counterpart to Don at that moment who’s sober, who’s assessing the two women in the elevator and his own feelings.

Will we learn if he’s really ever seen Diana before?

I can’t comment on where he’s seen her before. I think she’s very enigmatic. I think she looks very similar to a lot of women, obviously Sylvia, and Rachel Menken as well. She’s a very attractive woman. So there’s not a complete mystery as to what he’s interested in. But he’s so taken with her that it’s something that’s nagging at him. But it’s a bit open to the audience to interpret to what her hold on him is. I have spent some time thinking about it myself and certainly while we were shooting it. But there is something to the beauty of her magnetism.

Have we seen the last of her?

You know I can’t comment on that. I bet I can find a way to get fired retroactively.

And then there’s Betty, and her dreams of going back to school.

Especially within a scene that was so domestic. They’re doing a little teamwork to make a milkshake which is a classic American thing, a homemade beverage. The two of them chipping into do it together, which makes you wonder about the paths or the future that they could have had and how they diverged when Don did what he did and she did what she did. He’s relaxed, he’s got his coat off, one of the boys has his hat on. It’s a very pleasant family scene. But you are reminded as you always are that they’re not together by Betty going off to college which is a bit of a funny turn of events. She has a new future in her domestic situation but there’s something kind of lacking — and in walks Henry. Don has a last look of his family being shepherded by another father which is a powerful thing for Don. It makes him think more of Diana.

Yet Diana’s a woman who left her family.

I think that’s very hard for Don to understand, even though it could be argued that Don has not been the greatest father. That’s a tough one for him to swallow. I think a willful abandonment of his children would never cross his mind. He would always try to be as a good father as he can be. He might not always be the best father. But he truly wants to be a good father. He sometimes is.

Did you enjoy shooting the scenes with Megan and her family?

They worked very well as an actual family, going in and out of French and English. It made for a fairly funny series of events. I believed they were a family in how they could be close one second and fighting the next. That’s something families can do, transition in and out of that with ease, not hold on to the good things you were just thinking or the bad things, just shifting gears. That was nice to have her surrounded with family and remind you that she did come from somewhere, long before Don, especially now that she is looking to a future without Don.

Why have them talk to her in French and her answer in English?

I think part of is Megan is becoming a new person. Previously they would have spoken only French. She has moved to New York. She has married this man. She has become a different person. There is a bit of a subconscious expression of her new self when she does break into English. She slips into it without really knowing and feels she can express herself accurately in English or at least more innately. That comes through when she talks to her sister and the gloves come off — and it turns out the sister has a more provincial attitude. And then she’s no help at all to Megan, she’s nursing a hangover on the bed. And it’s her mom who’s packing everything up. And she’s more help than Megan ever wanted by sweeping the furnishings clean in the entire apartment. Julia (Ormond) was wonderful in all of that. She’s such an entertaining actress to watch. And then that last look she gives Megan. You don’t get to stand in judgment of me! And then of course there’s good old John Slattery, caught in the middle of the two women, giving us some entertainment. “It wasn’t my idea!”

John Slattery as Roger gets used for comic relief throughout this episode.

There is an interesting thematic thing that happens in the beginning when he has the two secretaries working for him. But it also reflects on Don, as everything does. There are two women, but there doesn’t need to be. They haven’t figured how to do their work in an efficient way, so they’re slowing each other down. Roger has to solve the problem the two women are trying to team up to solve. Shirley’s trying to be helpful but she’s out of the loop. One gets the sense that if Shirley were running the meeting, it would have gone more smoothly. Caroline wouldn’t be in there. Which is an interesting parallel to Don’s many women past and future that have been cycling through his life in this episode and in the previous one.

And then there’s the scene with Megan and Harry Crane. 

That was a real joy to shoot! That was a cringe-inducing moment for the entire crew on set, including Rich Sommer. You know the audience reaction when his hand goes on her hand, nobody’s going to be feeling good. But it’s more than just a creepy scene. It reinforces the idea of just how screwed Megan got by Don doing what he did. Of course she’s not going to sleep with Harry to get a job. But she’s in a position where she’s sunk slow. From an industry point-of-view she’s made so many bad choices that she’s having great difficulty becoming employed in her chosen field and she’s prey to someone like Harry. Not that she’ll give in to it. But we have seen her very successful. She was successful against all odds in advertising. She left it all and became successful as an actor. She’s exactly right when she says to Don, “I gave it all up because I believed you.” Look where she is. But I think Jessica (Pare) did a great job of bringing the pride and strength of Megan to those scenes. At least by the end of that meeting, the tables have turned, and by the time she leaves, she’s strong and he’s the one who’s cowering and he has to go to Don and try to come up with his stupid story about how she’s unstable and crazy.

Peggy stood up for herself with Stan. Is this another step forward for her in asserting herself? 

Pima got wrong completely this woman who’s supposedly such a strong female presence. She misjudged who’s in charge. She’s also a victim of assuming it’s the man when it’s actually Peggy who’s in charge. I think that Peggy drew strength and inspiration from her when she watches the cool ad that she’s making which is visually striking but then she reduces herself to almost prostitution in an attempt to further her business. Although Peggy can take valuable things from her, she’s not someone to emulate.

The episode ends with Don alone in an empty apartment. What’s next for him?

That was a shocking scene for all of us on set, to see that set clear of all of that wonderful furniture. We were coming to the end of shooting the entire season and to be on set with half of it gone was a sobering moment for all of us. I think it’s got him in a position where I hope the audience feels like “I can’t wait to watch next week.” It looks like Megan’s stolen all this stuff. All she wanted to take was Granny’s cabinet and the mirror. It paints Megan in a light that she didn’t want to paint herself in. But the point is that Don said he was going to sell the apartment. Now he’s in a unfurnished apartment. Who knows where’s he going to go?

This episode felt like the start of giving a sendoff to each character, one by one. Is that we can expect?

I don’t know in what form it will come, but I have every confidence Matt will give a satisfying send off to all of the characters.

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