*Warning: spoilers ahead*
After Don gives his car to the aspiring con man at the end of “The Milk And Honey Route,” he sits at a bus stop in Oklahoma in official, full-on hobo mode. He’s got just a bag of clothes and some cash, and he’s smiling. He’s given up the Don Draper life, even if he hasn’t given up the Don Draper name, and there’s joy in that freedom. All the while, Buddy Holly’s “Everyday” plays, and on the surface its lyrics fit the narrative.
“Everyday, it’s-a getting closer / Going faster than a rollercoaster / A love like yours will surely come my way.”
In Don’s case, it’s not so much a literal love; here what’s coming his way is true happiness. It’s getting closer (as is the end of the show, another layer here). It’s going faster than a rollercoaster. It’s a simple song, befitting Don’s suddenly simple situation. It’s pleasant and polite, the way old midwestern towns like the one Don’s in tend to be (as long as you disregard the occasional smack across the face with a book).
But there’s something else at play here. Mad Men fans like conspiracy theories. Even when Matthew Weiner openly shuts them down. One of the more popular conspiracy theories? That Don will turn out to be legendary real-life plane hijacker D.B. Cooper, or that he’ll ultimately meet his end in a plane-related tragedy. I won’t get into all the reasons why conspiracy theorists point to this outcome, but some cursory Googling will give you more information on that front than you can possibly consume in a day.
What does this have to do with that song?
It’s sung by Buddy Holly, who, you might have heard, died in a sort of famous way. A plane crash.
What does this hint at for Don Draper? Nothing. But I don’t think Matthew Weiner, an incredibly detail-oriented showrunner, would pick a Buddy Holly song to play over shots of Don, at the end of the show’s penultimate episode, without realizing the tie between Holly’s fate and what so many people with so much time on their hands think is going to happen to Don.
In other words, he’s having some fun trolling on his way out.