The pilot of "Mad Men", in large part, is about establishing the fact that the show takes place in a different time. The first thing to appear on-screen after the title sequence is a card explaining the name of the show—a term advertising executives in the late 1950s coined to refer to themselves. And the first thing we hear, before even getting an initial glimpse of the back of Don Draper’s head or a note of Jon Hamm’s husky voice, is Don Cherry’s "Band of Gold"—a pop standard recorded in 1955 about possession, purpose, and wedding rings as the sole signifier of personal happiness.
"I've never wanted wealth untold
My life has one design
A simple little band of gold
To prove that you are mine"
This song, along with the others in "Smoke Gets in Your Eyes", work to establish the world that the characters of the original Sterling Cooper Advertising Agency inhabit. The songs help create the initial dramatic irony of the series: as enticing as the privileged, booze-soaked world of Madison Avenue can be (and was for many viewers), we know that it will come crashing down as the decade progresses—the first of many, many fallow juxtapositions created by the show’s soundtrack.
Background music is often one of the most important sources of ironic contrast for visual media—something that the characters don’t (necessarily) experience, an opportunity for the artist to comment explicitly upon the action without having to add narration, clunky dialogue, or writing a critical interpretation of their own work. (All things that "Mad Men" showrunner Matthew Weiner has, basically, done—appreciate the relative lack of bluntness here.) They allow for a huge range of opportunities—for the series to leave episodes on big, bold notes, and for it to place characters in conjunction with something they don’t quite understand. And the musical choices that eventually became so prominent seem especially powerful when contrasted with what the characters themselves choose to sing and perform.
"Mad Men" is very much a show about performance, the characters’ who are often performing particular ideas of their roles or selves that have been dictated by the culture of the eras within the show. During the first few seasons of the show, "Mad Men"’s characters use their musical performances as a tool of presentation—creating their images through an approximation of art. And, unsurprisingly, when the characters themselves perform, it’s always old songs that are indicative of how behind the times they are.
Season three’s "My Old Kentucky Home" takes its name from Roger’s infamous blackface performance at an Old South-themed party, perhaps the most baldly out-of-touch, horrifying moment of naked privilege on a show full of them. This moment serves a striking number of purposes—it cuts Roger down from a place of authority almost completely. It gives Don an opportunity to demonstrate a certain level of poise and gain some viewer sympathy in his repulsion. Most importantly, it’s at once a gaping wound of bad taste and creates a friction that generates uncomfortable laughter and, therefore, the sense of simultaneous moral superiority and trans-historic, American horror that "Mad Men" trades in.
But this same episode also includes Paul Kinsey singing "Hello! Ma Baby", in an attempt to prove his masculinity to his pot-dealing Princeton buddy. Later in the episode, Joan plays the accordion, seemingly the least Joan instrument ever invented, as she acquiesces to her brutish future husband Greg’s demand that she distract their party guests. It’s not the first time Joan is objectified and practically made to dance for a man, and it’s certainly not the last, but it is one of the most expressive, as Christina Hendrick’s eyes are forced to do battle with her voice and hands. The very next episode ends with military standard "Over There", a song from World War I that reappears as late as the penultimate episode, when Don and his veteran buddies protect themselves in a nostalgia bubble.
On one level, these early performances serve a purpose of implicitly mocking the characters (how can anyone take Roger seriously after watching that?) but they also introduce one of the show’s long-term goals for what it’s trying to establish in its music choices—the characters are in large part creations of their environments, raised on a decaying pop culture meant to communicate a set of values that simply cannot hold as the decade progresses. One of the threads of the third season is a commercial replicating the opening of "Bye Bye Birdie"—which first belies Sal Romano’s closeted homosexuality when he engages too strongly in the performance for his wife, then gets him fired when he refuses to give in to Lee Garner, Jr.’s advances. No one is capable of owning themselves, or even understanding what it would mean to take ownership of themselves. No one is quite the right man or woman for their time.
Put another way: none of the characters who originally populated "Mad Men" fit well into the world they were eventually forced to inhabit. The first time the show deploys a full-on 1960s pop smash, the kind of song viewers will instantly recall in 2015, it’s "(I Can’t Get No) Satisfaction"—a song full of musical aggression and swagger while not-so-subtly hiding a deep emotional hole in its lyrics that plays while an adrift, divorced Don emerges from a swimming session. (Again: it’s not very subtle.) Yet by the time the show has reached the summer of 1966 at the beginning of its fifth season, however, a generation has appeared that’s capable of controlling the narrative for themselves, something the show announces with thunder and flair:
Megan’s performance may be a birthday gift to her appalled husband, but it’s also legitimately thrilling, something she clearly enjoys doing. The once and future actress claims ownership over herself and her singing, flaunting her attractiveness without having to use it as a weapon (à la Joan) and unwilling to hide it for professional advancement (à la Peggy)—everyone is going to accept her on her own terms. (Notice that she’s allowed to own each frame, rather than being boxed in the way many other female characters are.) It’s a star-making moment for both Megan and the actress that plays her, Jessica Paré, and a demonstration of how weak and out of place Don is in his new relationship (though several other men holler during the song, Don is mute).
Don’s silence, and the bombast of "Zou Bisou Bisou", is a strong indicator of the attitude "Mad Men" took toward its music as it aged. Even more than in the earlier years, it became a show that thrived on obvious symbolism, deploying just subtly enough to flatter viewers who pick up on it—but also one that takes obvious glee in using that first layer as a mask for nuance, things that only reveal themselves on further viewings. The brilliance of "Mad Men" lies in that it is always subtext and text and sub-subtext, at all times bludgeoning you with Meaning while hiding the real meat, all nestled within a veneer of gorgeous, masterfully crafted television. When Don drives off to St. Paul—leaving his new old life as a McCann servant behind yet again—literally to the tune of "Space Oddity", it’s hard to claim that the series is taking even remote precautions with its music. We’re left with clear images: Don Draper as an astronaut, lost in space.
Still, more often than not, even "Mad Men"’s most on-the-nose soundtrack choices explicitly serve to create an illusion. In the season seven premiere, the Spencer Davis Group’s "I’m a Man" introduces a newly jobless (for the most part) Don as he shaves, gets himself ready, and heads to Los Angeles to meet Megan, who he is lying to about his employment status. She appears in slow motion, looking drop-dead gorgeous, treated by the camera as an object important in her relation to Don—but that’s just how Don sees himself, or how he wants to see himself and his marriage, or how we want to see him. The moment the song fades out and time returns to normal, the couple get into a fight, presaging the impending end of their marriage. The situation is reversed at the end of the episode, when Vanilla Fudge’s "You Keep Me Hangin’ On" adds a sense of apocalyptic fury to Don’s inability to let himself go, to shed the last vestiges of his old life. While the show creates the impression that Don is going to fall off the roof, he’s denied that freedom, framed as being trapped by prison bars.
As Mad Men’s musical selections became more prominent (increasingly used to close out episodes with a big statement), they moved in the direction of "The Sopranos"’ final music cue—unbelievably blunt, a little ridiculous, and, at a certain level, pretty cheesy (to the point where the explanation given by David Chase, Weiner’s mentor in the "Sopranos" writers’ room, rings knowingly false). Take the most sentimental the show has ever allowed itself to be, toward the end of season seven’s "The Strategy"—a scene that provides a plausible culmination of Don and Peggy’s work-soulmate relationship. Their fleeting connection invokes the same syrupy quality as, say, "Band of Gold", but without the sense of hollowness and unease that accompanies something like the first season’s ending, ambiguously tracked by Bob Dylan. This is just two people who understand each other, if only for a moment.
In the moment, both Don and Peggy seem to, for once, effectively identify with the message of a song they’re listening to—both have, in their own, divergent manners, gone their own way. That this might be the most connection two characters are allowed to have to a piece of music suggests that, the whole time, "Mad Men" has been telling a story about pop culture, at least in part. If we can look back and say that "(I Can’t Get No) Satisfaction", "I’m a Man", or "Space Oddity" express or capture something about the times in which they were recorded and entered the cultural consciousness, we must also acknowledge that there is music being made today that does the same thing—and that, as much as we try to consume, we probably haven’t heard or connected to it.
Much of "Mad Men" is about constructing narratives about our lives—Don’s transformation from Dick Whitman, Betty’s repetitive emphasis on the roles everyone in her family should play, and, of course, the entire advertising business. Pop culture can be helpful when it enters those narratives, but it can also be stifling, and deny us the critical distance to understand what is actually happening to us and why. So the end of the fifth season literally turns Don into an unwilling James Bond, trapped by the patterns and demands and habits of the character he’s forced himself to play, interminably doing the same movie after another, growing weary of their cheap pleasures.
The woman at the bar asks Don if he’s alone, and we know how he answers (he is), but we’re right there with him, alone in spirit, ordering an old fashioned long after being old fashioned stopped being a desirable quality. Don Draper is a man out of time, for all of the obvious reasons, yes, but also because none of us are capable of being of our times, at all times. Even Peggy, who appears to have fully embodied a more aggressive spirit of the 1970s with her carefree entrance to McCann Erickson, felt very distanced from the problems of most people she knew for the last few seasons—as unpleasant as she acted during those years, she’s only human. That tenuousness, that even if you can fully inhabit one moment, you’ll be spit out the next, is reinforced in "Mad Men"’s most important musical statement—that moment in season five’s "Lady Lazarus" when Weiner bought the Beatles and shut them down.
Earlier in the episode, he asks, "When did music become so important?" By the end, doesn’t have an answer to that question, nor either of the more pressing ones: why did music become so important, and how can I understand it? Turning off the Beatles in the middle of "Tomorrow Never Knows", Don proves completely unable to grasp the change it signified. His question isn’t even about the meaning of art, or how culture is capable of shaping our collective ideas about the world—it’s about music’s importance to his job. Don is profoundly incapable of grasping the intangibles of music, the things that inspire people to write about it professionally and allow at least a few people to succeed.
The power of "Tomorrow Never Knows" doesn’t lie simply, or even primarily, in its statement about Don as a character. Instead, it puts us in the position of lording our own knowledge of the Beatles’ success, and our presumption of their brilliance, over the clueless white guy on the screen—a judgment we only get to make because we live in a world where the Beatles are an institution. Pop culture means something different in 2015 than it did in 1959 than it did in 1965 than it did in 1970, and the only constant is that it will shift under our feet until we are all stuck ordering old-fashioneds. As much as we would like to tell ourselves that, were we alive in 1966, we too would have loved "Tomorrow Never Knows", the opposite is far more likely. The Don Draper of 2015, whoever he may be, almost certainly loves the Beatles.