I’m a rolling stone, all alone and lost / For a life of sin, I have paid the cost
When I pass by, all the people say / “Just another guy on the lost highway”

Season 4 is still answering the question, “Who is Don Draper?” As everyone else has pointed out, we’ve seen Don change this season, evolving and adapting to all the other change surrounding him. The good folks at Entertainment Weekly, as well as The Nation’s Greg Mitchell, have made arguments that the inner-Draper episode (4.8 “Summer Man”) parallels Dylan’s most famous song, Like a Rolling Stone. However, much like Don Draper, the song has many layers, and within the origins of Dylan’s six-minute indictment of pride is a song that better reflects the sense of lost/loss Draper has gone through in these last four episodes.

Just a deck of cards and a jug of wine / And a woman’s lies make a life like mine
Oh, the day we met, I went astray / I started rollin’ down that lost highway

Leon Payne was a blind balladeer. One day in 1948, on his way from Texas to California to visit his sick mother, he wrote the song “Lost Highway.” The song was made popular by Hank Williams first, and then Bob Dylan played it with Joan Baez during the 1965 film “Don’t Look Back.” Many Dylanophiles think this was the song that inspired Dylan’s most popular song, “Like a Rolling Stone.” The song (the lyrics of which I’m interspersing throughout this post) is a simple ballad whose main character has lived a sinful life and is now lost. Throughout these four episodes — from hitting rock bottom (“The Suitcase”), to writing memoirs (“Summer Man”), to trying to turn his life only to learn his daughter is now the one who is running away (“The Beautiful Girls”) to witnessing his past lies smash into his work world (“Hands and Knees”) — Don has tried to be honest about who he really is, where his life has taken him so far, and how he can move in a new direction to improve himself.

I was just a lad, nearly twenty-two / Neither good nor bad, just a kid like you
And now I’m lost, too late to pray / Lord, I’ve paid the cost on the lost highway

I’d imagine that by the end of the last three episodes of this season, we’re going to have a much different answer to the question, “Who is Don Draper?” But for the first time since we’ve gotten to know him, I’ve started to feel like he’s someone I can root for. He’s at least trying to be a nice guy now. When his secretary effed up his file for the Department of Defense, he didn’t berate her or fire her. He accepted his own role and his own fault. That’s a big move for Draper. Of course, on the other hand, he’s still lost, and as Elise pointed out, he’s still running from who he really is.

Now, boys, don’t start your ramblin’ round / On this road of sin or you’re sorrow bound
Take my advice or you’ll curse the day / You started rollin’ down that lost highway

Will Don Draper be able to get off the lost highway? More so than any time watching Mad Men, I’m excited to find out that question.

—Phillip

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