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One of the best things about Mad Men is how weird it's willing to be

Roger plays the organ. Peggy roller-skates. It's beautiful.
Roger plays the organ. Peggy roller-skates. It's beautiful.
Emily St. James was a senior correspondent for Vox, covering American identities. Before she joined Vox in 2014, she was the first TV editor of the A.V. Club.

Every week, Todd VanDerWerff will be joined by two of Vox's other writers to discuss the previous episode of Mad Men over the course of that week. Check out the recap for this episode here, and follow the whole discussion here. This week, Todd is joined by education reporter Libby Nelson and political writer Dylan Matthews. Keep checking in all week long for new entries.

Todd VanDerWerff: One of the things I'll miss most about Mad Men are those surreal flights of fancy that make the show so much fun to watch. The more unexpected they are, the better.

That's what I loved about Roger playing the organ. I'm sure it was set up in some previous season or episode, and I'm sure if I went digging around for it I would find the explanation for Roger's musical genius. But I almost don't want to do that. It's so much better as this random side gag that comes out of nowhere with just three episodes to go.

It's that weird sense of humor that kept Mad Men going all these years. It's not exactly a new observation that the show is as funny as — if not funnier than — some of the best comedies on TV, but even in the show's most dour, repetitive stretches, it would come up with grace notes around the edges of the story, ones that played up the strangeness of the Mad Men universe.

What's been notable about the series as it's gone on is how much that approach has started to creep into the show's drama as well. The first season had a couple moments where some off-the-wall notion was played completely straight, but for the most part the first season's oddities were things like Betty gunning down pigeons in the backyard — important character beats but also moments that were clearly intended as dark jokes.

The show has gotten more daring about presenting these weird drama moments over the years, and it quite possibly culminated in "Lost Horizon," which is an episode so filled with these bits that Entertainment Weekly proposed, in all seriousness, that Don Draper picked up a metaphorical time-traveling Bob Dylan at the end of the episode, and I found the argument halfway convincing. Metaphorical time-traveling Bob Dylan? Sure! Why not?

I spent much of my first entry in this series talking about the final season's similarities to Breaking Bad's final season, but we could broaden that out to talk about how the two shows shared a similar streak of surreal humor. Breaking Bad took place in a Coen brothers–influenced world full of sick, dark humor. Some of its best moments were the sorts of grotesque — yet hilarious — sights that you couldn't see anywhere else, like a man's head being attached to a turtle.

On Mad Men, however, this approach to storytelling has always felt special, because it's rooted in the sorts of things that happen to us in our daily lives. Everybody has that experience of walking down the street, then having their journey waylaid by some unexpected, slightly strange thing that happens. Mad Men simply heightens that sensation.

Not to bring everything back to that plane Don spots flying over Manhattan in this episode, but that moment captures so nicely the way that looking out the window can break up a humdrum day and make work seem that much more monotonous. This is a very good, small-scale example of how Mad Men approaches this storytelling method.

There's a history of sophisticated dramas using their surreal streaks to advance their stories in unexpected ways. The progenitor of this approach was probably the '80s hospital drama St. Elsewhere (a show that planted so many of the seeds that have blossomed into our current drama boom), but it really took off with Twin Peaks, where weird stuff happened almost as a matter of course. Sopranos showrunner David Chase was heavily influenced by Peaks, and his show consequently contained many weird moments and twists.

Yet this particular storytelling style seems as if it's dying out just a little bit. As much as I love The Americans, it's a much more deliberate show, with less room for flights of fancy. The same goes for Game of Thrones, which could break its carefully constructed fantastical verisimilitude if it got too weird. Then there are shows like Orphan Black, which seem to be constructed entirely out of weird story turns and, thus, cause them to lose some of their power.

When Mad Men ends, it won't be the end of this particular style of storytelling entirely — Rectify is pretty good at employing it — but it will feel like it's been significantly reduced on TV. I think that's because so many of our great dramas now are basically genre tales, and genre requires a certain amount of steadiness to keep from coming apart at the seams. But when this show goes, I'll miss the weirdest, most unexpected parts of it the most of all.

Read the recap, and check back tomorrow for thoughts from Dylan.

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