25 Best ‘Mad Men’ Musical Moments

When we first meet Don Draper (Jon Hamm), we see his best self: a smooth-talking, impossibly suave ad man, grilling a waiter about his brand of cigarette — all in the name of research, of course. The interaction takes place as crooner Don Cherry's version of "Band of Gold," a hit when it was released in 1955, plays over the soundtrack. Yes, it's a fairly traditional choice — but then, Don seemed like a fairly traditional guy at the beginning of the series, a man's man who drinks Old Fashioneds, smokes Lucky Strikes, and looks damn smart in a suit.

It can be hard to remember now, but when the series began, Peggy Olson (Elisabeth Moss) was just another girl in the typing pool, and Pete Campbell (Vincent Kartheiser) was simply another smarmy salesman. Even though their relationship eventually settled into one of begrudging respect, it began a brief fling before the whole thing imploded (and resulted in an unfortunate pregnancy). One of the most memorable moments from their tryst happens in this episode: The whole office is drinking at P.J. Clarke's when someone puts Chubby Checker's dance-inspiring hit on the jukebox. Hips are twisting; inhibitions are loosening. And then Peggy slinks her way over to surly Pete — who drunkenly spurns her.

"Nostalgia — it's delicate, but potent." Don's pitch for Kodak's slide projector is a stunner, using snapshots of the Drapers (their wedding day, Betty pregnant, the kids as babies) to sell the idea that you can time travel through the magic of photos. But as much as the ad man is winning at work, he's failing at home: The pitch happens on Thanksgiving, and though Don hurries back to meet his wife and the kids before they leave for her dad's house, he just misses them. Dylan's classic tune, about a painful split, plays over him sitting, dejected and alone — foreshadowing what's to come for the couple.

It's fitting that an episode centered around the idea of womanhood and its trappings would begin with a montage of Betty Draper (January Jones), Joan Holloway (Christina Hendricks), and Peggy getting ready in the morning. Betty adjusts her prim white underthings; Joan pulls on a blue slip over a black bra; and Peggy, somewhere in between the Marilyn-Jackie dichotomy the episode sets up, dons modest stockings and a slip. The sequence is offset by one of the rare instances of contemporary music being used on the show: The Decemberists' thundering track from 2005's Picaresque. The song, about a woman being worshipped in ancient times, is a stark contrast to the women of Mad Men trying to find their footing as the world changes around them.

One of the central conflicts of Mad Men has been how its characters deal with the rapidly changing decade in which they live. Often, the musical choices reflect that, or at least nod to it — in this case, the Telstar satellite launch of 1962, which inspired this song by British band The Tornados. Pete and Don are on their way to an aerospace convention, and the tune begins playing as Don stares out the plane's window. And while it signals the future in an obvious way — the space race and changing technologies — it's also a nod to Don, seeking a new future in Los Angeles as his relationship with Betty is falling apart. (It's a theme that would be repeated throughout the series.)

One of the third season's pivotal plotlines centers around Sterling Cooper's attempts to create a campaign for Pepsi based on the wildly popular teen musical, Bye Bye Birdie. But like so many advertisers who've tried to capitalize on trends, they realize it's not working because they're missing one essential thing: Ann-Margaret. Even though the soda pitch wasn't successful, the musical's presence did lead to a brilliant off-the-set moment: a viral video from the cast and crew's season-three wrap party, with everyone drunkenly karaoke-ing the title tune for Matthew Weiner.

In what's surely one of the show's most uncomfortable scenes, Roger Sterling (John Slattery) dons blackface and sings "My Old Kentucky Home" at a Kentucky Derby party. As Weiner told Vulture, "that episode is about white people and what they're like when they’re alone" — in this case, donning shoe polish for a little casual racism. Slattery also noted in an interview after the fact that "it's horribly offensive, obviously, but this is the point. This is where we were. It was so commonplace. This is the message, and Roger's the messenger." Not even Pete and Trudy dancing the Charleston later on can lighten the mood after that display.

A company lives or dies on its PR — and the newly formed Sterling Cooper Draper Pryce is floundering, thanks in part to Don’s evasiveness in an interview with Advertising Age. That ends up screwing the company out of a new account, and by the end of the episode, Don is mythologizing SCDP's founding in an interview with the Wall Street Journal, in an effort to repair his reputation. But the story he tells — "I walked into Lane Pryce's office and said, 'Fire us'" — is contrasted with the spot-on "Tobacco Road," by British Invasion band the Nashville Teens. "I was born/in a trunk/momma died and my daddy got drunk" is basically Don's life story, one very different from the public image he projects.

Matthew Weiner doesn't always go for the obvious when it comes to choosing Mad Men's soundtrack, often preferring to use songs that are semi-obscure or quirky to make a point. But when he does go for the low-hanging fruit music-wise, he makes it work. This episode takes place in the summer of 1965, when "Satisfaction" had just been released as a single and spent several weeks on the top of the Billboard charts. So when Don hears it blasting out of somebody's radio, it makes total sense for the time — and for emphasizing how his type of Madison Ave. man in the grey suit will soon become irrelevant. (We can forgive Weiner for making sure that the song's most dismissive lyrics about ad men are juxtaposed with Don in his clean white shirt — obvious, yes, but also kind of perfect.)

Don's surprise proposal to his secretary Megan at the end of season four comes after a period, following Anna's death, in which he tries to redeem himself. (Poor Dr. Faye, who ends up getting screwed over in the process.) And maybe Don really did think that young, pretty, seemingly carefree Megan would help him, in his words, feel like himself. Of course, we now know that's not true — and the choice of Sonny and Cher's sappy little love tune at the end of the "Tomorrowland" episode seems ironic in retrospect. And lest we forget, Sonny was 11 years older than Cher, and they were collaborators before they were lovers. Coincidence? Doubtful.

Jessica Paré went from a relatively unknown actress to the show's next-big-thing thanks to Megan Draper's sultry, over-the-top performance of this quirky French ye-ye tune. But beyond the sex-kittenish aspect of it, her display — which comes during a surprise 40th-birthday party she arranged for Don, a setting that clearly makes him uncomfortable — also serves to underscore the deep difference between the couple. Megan is younger, cooler, and thinks that Don will appreciate the production being made over him; he's embarrassed by the party, the hullabaloo, and most of all, his wife flaunting her sex appeal in front of their coworkers. Clearly, this is a match that will last, er, forever-ish?

Taken literally — very literally — it's easy to see why this Beach Boys tune was used to score Roger’s first experience with LSD. Pet Sounds, a harbinger of psychedelic pop, would naturally figure heavily into a subplot that emphasizes a drug trip, right? But dig a little deeper and it's clear that this is more of a reference to the dissolution of Roger's relationship with his much younger wife, Jane. The hallucinogenics allow them to be open about their mutual failures, and by the episode's end, they've parted ways. "Each time things start to happen again/I think I got something good goin' for myself/But what goes wrong" — it's as relevant a line to Roger Sterling's life as any.

Using the Fab Four's music doesn’t come cheap: The snippet from the trippy final track off of 1966's Revolver that closed out this episode cost a cool $250,000 to license. But the expense was worth it just for the image of Don, sitting in his swanky Lied Mobler recliner, attempting to understand what The Kids were into. Despite his dalliances with hippie women and pot, Don isn’t a fan of the swirling psychedelia-inspired track (which Lennon allegedly composed after tripping on acid) — he turns the track off midway through. And the fact that it's juxtaposed with Peggy and Stan smoking pot in the office is surely coincidental, right? Right.

The crunchy opening chords of the Kinks' 1964 hit single: Is there a more perfect soundtrack for a new era for Peggy Olson? After being shut out by her fellow (male) copywriters, and humiliated by Don — who throws money at her when all she wants is a little respect — Peggy finally takes charge of her career, accepting a better offer with Cutler, Gleason and Chaough and quitting SCDP. After a surprisingly tender moment with Don, she clears out her office and leaves that world behind. But the small smirk on her face as she steps onto the elevator and that iconic riff kicks in…it says everything.

Sure, the James Bond theme about living two lives — now who could that apply to on the show. (If you raised your hand and yelled out "Dick Whitman," congratulations!) The Nancy Sinatra song also adds an air of mystery to this season, which essentially ended on as much of a cliffhanger as Mad Men allows: Don's smoking and drinking at a bar when he's approached by a woman who asks, "Are you alone?" We know he's not; our hero just walked away from helping his wife kick-start her career. But will he stick with that life, or the one of his dreams?

As Mad Men slouched toward the Bethlehem of the late Sixties, its characters found themselves butting up against the fringes of the counterculture. Case in point: Joan and her friend, Kate, end up at the Electric Circus, the St. Marks Place nightclub that was a favorite of Andy Warhol, the Velvet Underground, the Grateful Dead, and a variety of other turned-on, tuned-out longhairs. True to the spirit of the place, Joan lets her guard down and makes out with a stranger, with the sultry French singers cooing at each other in the background. Tres chic, man.

Like "Satisfaction," the use of this 1968 story song functions more as a period piece than any kind of deeper dive into the characters' psyches — but what a period piece it is. The smash C&W single tells the story of a woman in a small town who calls out the locals after she's criticized for wearing miniskirts ("Well this is just a little Peyton Place/and you're all Harper Valley hypocrites"). It provides the soundtrack for a freewheeling Los Angeles party attended by Roger, Don, and Harry Crane; there are hippies, girls in minidresses, and former SC ad man Danny Siegel, who’s now a caftan-wearing film producer. Another reminder that the world is moving on, and many of these Mad Men are still stuck in the past.

Don begins and ends this episode the same way: depressed and curled up in the fetal position. He's distracted at work and alienating his co-workers; his latest extramarital relationship, with his neighbor Sylvia Rosen, ended abruptly; and, oh yeah, the adultery skidded to halt because his daughter caught them mid-dalliance. His misery jam: this deep cut from the Monkees' ill-fated 1968 film, Head. Written by the inimitable duo of Gerry Goffin and Carole King, "Porpoise Song" is one of those songs that somehow manages to explain a bit of Don’s psyche in a nutshell. "Wanting to feel/to know what is real/living is a lie" — that's Dick Whitman, all right.

Joni Mitchell's elegiac rumination on lost youth and disillusionment is especially appropriate at the end of the sixth season. Don, unmoored and shaking from DTs, unloads about his tragic past in a meeting with Hershey rather than selling another lie. His honesty costs him his job, but it's so freeing for him that he's willing to open up about his past with his family. Don takes his kids on a cheery Thanksgiving jaunt to see the whorehouse where he grew up, revealing at least a part of his true self. His whole life has been an illusion, but maybe — like Mitchell — he's willing to admit it, and look at the facade from both sides. 

It's the beginning of the end, and Don seems like his old self: clean-shaven and strolling out of an airport in his fedora, a smart suit, and slick shades. But when he meets Megan at the airport in Los Angeles, it's immediately clear that something isn't right: She won't let him drive her car and has her own routine without him, even getting mad when he buys a TV for her house. Meanwhile, this 1967 song by the Spencer Davis Group ("I've got to keep my image while suspended on a throne/That looks out upon a kingdom filled with people all unknown") speaks more to Don's actual situation: He's jobless, practically homeless, and deeply, profoundly lonely.

Speaking of Don's loneliness, the season seven premiere ends on a pretty bleak note — and not just for the show's hero. (Although the image of him sitting on his balcony in the freezing cold, seemingly in the middle of a breakdown, is pretty bad.) After butting heads with SC&P's new creative director, Lou Avery, and being reminded of her disastrous affair with Ted Chaough, Peggy breaks down sobbing on the floor of her Upper West Side fixer-upper. Vanilla Fudge's plaintive cover of the Supremes hit song, plays the episode out, and damned if it doesn't speaks volumes. "Why don't you get out of my life/And let me make a new start?" could just as easily apply to Don and SC&P, or Peggy and Ted, or Peggy and Lou. Take your pick.

Women may come and go in Don's life, but there will always be one constant: Peggy Olson, his protege-turned-peer. And much like the landmark Season Four episode "The Suitcase," this episode focused on their relationship, as they find their way back to each other and work their magic as a team once more (for Burger Chef, of all things). They open up to each other — with Peggy admitting her anxiety about turning 30 — and realize that they are, in a way, family. Sinatra's "My Way" comes on the radio, and the two share a dance; it’s a sweet moment for Don and Peggy, who've always had a bond that skirts the line between mentor-mentee and father-daughter. In this moment, it certainly felt like the latter.

The death of Bert Cooper (Robert Morse) was not a surprise, per se, but sad all the same; luckily, Weiner and the show gave the character, and the actor who played him, a lovely send-off. Before Mad Men, Morse was best known for playing the conniving J. Pierrepont Finch in How to Succeed in Business Without Really Trying, and Cooper's exit was a nod to the actor's Broadway past. After his death is announced at SC&P's office, the late co-founder appears to Don in a dream-like sequence, singing the old standard with a chorus line of secretaries behind him. In an interview with Rolling Stone after the episode aired, Morse explained it this way: "It was Bert telling Don: What are you doing? All this shit that you're doing, cut it out. The best things in life are free." Whether Don get Bert's message from the beyond is harder to parse.

Matthew Weiner recently admitted that he had considered using Peggy Lee's forlorn tune as the theme to Mad Men — the main reason held back, he claimed, was because it was released in 1969. But the song is a perfect coda for this episode, in which everything and nothing has changed for the show's central characters. Even though they're now part of McCann Erickson and extremely wealthy, it's the same as it ever was: Peggy and Joan battle sexism in the workplace; Pete feels underappreciated; and Don and Roger are drinking heavily and womanizing. They've gotten what they thought they wanted — respect, money, freedom — but it's not enough. And like the song says, if that's all there is, may as well break out the booze and have a ball.

As Mad Men wraps up, Don has all but ditched his real life — his job at SC&P, now absorbed by McCann; his wife, who got out of their relationship with $1 million; and even his children — in favor of some kind of soul-searching journey out west. His self-isolation parallels Bowie's Major Tom, who, at the end of the Thin White Duke's 1969 hit, has asked Ground Control to send a message to his wife and trusts his life to his spaceship. He's leaving the world as he knows it behind. So will we see a new beginning for Don, or will he simply float along in his own little tin can, far above the world? Only time — and the series finale — will tell.