Dylan & Draper: Will Don Paint His Masterpiece?


During an episode initially focused on the past, Don thinks about how to shape his future. (Credit: AMC)

“Someday, everything is gonna be different,
When I paint my masterpiece.” – Bob Dylan, “When I Paint My Masterpiece” (1971)

“When I Paint My Masterpiece” is a 1971 song written by Bob Dylan. It is a song about traveling to foreign places and seeing the wonders of the world, and ultimately one about an individual’s quest to achieve creative and personal satisfaction. It is a song about where a person and civilization has gone, and where one hopes to eventually arrive. It is a song performed by The Band, frequently covered by The Dead, and this week provided the thematic framework of one of the final five episodes of “Mad Men”, a show based during a decade where Dylan’s words were as powerful as any.

This week’s episode, titled “The Forecast,” initially appears to be one about conflict and war, both of the past and the present. Roger orders Don to write the agency’s version of the Gettysburg Address. Betty and Sally discuss colonial Williamsburg. Mathis thanks Don for fighting for him, Joan’s date asks her whose side she is on, Bobby and Gene play with guns, and Glenn decides to go to Vietnam. Characters blame each other for failed objectives, whether it’s the sale of an apartment or the correct creative approach for a peanut butter account. Adults express pride and optimism about the war while teenagers disagree over its purpose. But the episode eventually shifts to one about acknowledging the battles of our pasts to how we shape what is left of our futures. As Don paraphrases Lincoln’s words, he adds an optimistic twist, saying that we know where we’ve been and we know who we are, “let’s assume that it’s good, and that it’s going to be better – it’s supposed to be better.”

It’s not a surprise that when the agency needs someone to forecast the company’s goal for the future – to paint its masterpiece – the task falls to Don, the firm’s central artist for the last 15 years. He asks the Peter Pan team to give him “the broad strokes,” and is told by Ted that he is “so much better at painting a picture.” But the project takes on a larger meaning for introspective Don, and he seems disappointed that is colleagues do not be seem to be thinking the same way. Ted, less than a year removed from wanting out of advertising entirely, dreams of landing a pharmaceutical account. Peggy, having climbed from secretary to copy chief, dreams of titles and catchphrase fame. Neither is willing to admit to the out-of-office life objectives that Don knows each of them have. After letting work serve as distraction for so many years of his life, Don is frustrated that so many around him fail to provide an ambition that extends beyond the four walls and two floors of SC&P.

Dylan’s song mentions European cities (Rome, Brussels) and man-made structures (the Spanish Steps, the Coliseum) as stops on one’s quest for satisfaction, and this week’s episode similarly refers to such places as symbols of where one goes when professional success is achieved and something more important is sought. Don instructs the realtor to tell customers that the previous owner got rich and moved to a castle in France, and Joan’s date (after eating French cuisine) becomes frustrated that her son will keep her from going to see the pyramids with him. But the narrator’s contentment with those places is temporary, as he soon longs “to be back in the land of Coca-Cola.” (Ironically, this week we see Roger offer Don a Coke.) In effect, the figure realizes one can only learn so much by looking back, and that he must move things forward regardless of what has already happened. Similarly, several characters have to accept the reality of their current situations – that Joan is a twice-divorced mother of a four-year-old, that Sally is the daughter of Don and Betty, that Don’s apartment reeks of failure – and try to make the best of it.

Painting one’s masterpiece is not necessarily about traveling to a particular place or seeing a particular sight, nor is it necessarily the achievement of a particular accomplishment. The beauty of Dylan’s song is the level that it is open to interpretation, and Don realizes that so too is the idea of forecasting what the future will look like. His secretary thinks it will resemble the World’s Fair. Glenn thinks it will include him returning from the war to be with Betty. Sally’s friends want it to be one where they are senators and delegates; Sally just wants it to be one where she is away and different from her flirtation-oozing parents.

Though we don’t receive total closure in this episode on what Don envisions for the future, viewers can take solace in the fact that Don is at his best when he is looking forward. It is the mindset that allowed him to shed his tattered Dick Whitman past and to become the millionaire he is presently. It is the advice he gave to Peggy after she gave birth to Pete’s child (“Get out of here and move forward. This never happened. It will shock you how much it never happened.”), and to Lane when he told him to resign (“Tell them the next thing will be better, because it always is.”). It has even inspired some of his best creative work: “The future,” he planned to pitch to Chevy, “is something you haven’t even thought of yet.”

This question is hardly novel for a series that has always grappled with the existential questions like the meaning of life and the reality of true happiness. But after recent episodes that, on the surface, appeared to be odd detours for viewers, “The Forecast” puts on a more direct road a series drawing closer to its final stop. It is a road on which Don demonstrates signs of optimism, telling his realtor he has a good feeling and encouraging her to share in having “a little glamour, a little hope.” It seems, for the moment, the question is not whether Don will paint his masterpiece, but when he will do it and what it will be.


– Bob Dylan and “Mad Men” have a long history. The Season 1 finale, “The Wheel,” ends with Dylan’s “Don’t Think Twice, It’s Alright.” Season’s 3’s “Guy Walks Into An Advertising Agency” ends with Dylan’s “Song To Woody.” Additionally, during Season 2, Peggy plans to see a Dylan concert in the Village with then-creative worker Kurt.

– Don tells realtor that a lot of good things happened at his Upper East Side apartment, but I struggle to think of any. It is where he had a surprise 40th birthday party he didn’t want and didn’t enjoy; where he killed an ex-fling during a fever dream; where he was robbed by a thief who terrified his home-alone kids; where Megan would sleep while he cheated on her with his neighbor one floor below; where he had a door slammed on his face by Sally after Sally walked in on him with said neighbor; where he stayed in confinement rather than be in California with his wife when on exile from his company; and finally where he had all of his possessions (alarm clock included) moved out by his second ex-mother-in-law. But yes, other than that, the place was filled with wonderful memories.

– When Don uses the office vending machine, a Hershey bar is prominently featured in the middle of the row of candy, a powerful of a symbol as any of Don’s breakdown during the Season 6 finale. His past is also brought up later, when Sally makes sure to let her friends at dinner know that her father grew up poor.

– But as Sally’s friend points out, Don grew up poor and ended up in a penthouse. Don purchased his Upper East Side apartment for $75,000 sometime between late 1964 and early 1965. He sells it for $85,000 roughly six years later.

– It speaks to the quality of character development on the series that a scene with three characters – Betty, Sally and Glenn – who have been pushed to the show’s margins for several seasons can still carry so much weight. Glenn arrives at the Rye home for the first time and asks for Mrs. Draper, is reminded she’s now Mrs. Francis, and minutes later is calling her Betty. Their history started when she gave him a lock of her hair when babysitting him during Season 1 when he was 10 years younger. He has become one of Sally’s few true friends, and she is justifiably crushed to hear of his decision to enlist as well as the flirtation between the two that she is able to pick up on.

– In Season 4 finale (the last time Betty sees Glenn), Glenn is let into the Ossining house by then-maid Carla to see Sally, and their meeting is intended to be secret from Betty. This week, Glenn is let into the Rye home for his second visit by now-maid Loretta to see Betty, and their meeting is intended to be secret from Sally.

– Sally’s skepticism and fear of impersonation when signing traveler’s checks reminds the viewer of Lane forging Don’s signature on a check when he embezzled money from the agency.

– During the first half of Season 7, we learn of Lou Avery’s side project, a comic titled “Scout’s Honor.” It is about a monkey in the Army who struggles to follow orders, fitting into this week’s military theme. The L.A. office secretary mentions his recent meetings at Hanna Barbera animation studio, which was launching the “Josie and the Pussycats” cartoon in 1970 after the success of “The Flintstones” and “The Jetsons” during the 1960s.

– Joan’s son Kevin watches Sesame Street, which was in its inaugural season during 1969-1970. Bobby tells Betty that they want to watch “The Brady Bunch,” which also had just launched in the fall of 1969.


Don Does Disney: It’s A Small World After All


From milkshakes to wedding rings, this week’s “Mad Men” presented many symbols of a happier time in Don’s past.  (Credit: AMC)

This week’s episode of “Mad Men” presented a taste of Disney, from the mentioning of Peter Pan Peanut Butter to the official (and expensive) conclusion of an always-doomed marriage born in Disneyland itself. Don proposed to Megan in the Season 4 finale titled “Tomorrowland,” though justifiably-skeptical viewers always deemed “Fantasyland” a more appropriate birthplace for the marriage. Ironically, it is in the Fantasyland section of the Disneyland theme park where the It’s A Small World ride is located, and in this week’s episode (titled “New Business”), our protagonist Don Draper is consistently reminded that life is indeed a small, small world.

As we move closer to the conclusion of series, things are coming full circle for Don. During “Tomorrowland,” it is Megan’s cool and calm reaction to a milkshake spilled by Bobby that causes Don to view Megan as the anti-Betty; he proposes to her later that night. Flash forward to 1970, and Don is again sharing milkshakes with his sons, but this time on good terms with Betty and instead preparing to finalize his divorce with Megan. On that same trip to Disneyland in Season 4, Don receives the wedding ring bequeathed to him by Anna Draper, which he later offers to Megan. Skip forward again, and Megan is returning that very ring in the divorce attorney’s office (after, of course, getting her $1 million check – things sure have changed since Megan told Don last summer that he didn’t owe her anything).

As Don says au revoir to the French Canadian chapter of his past, he is reminded just how small this world really is, both in terms of his relationships and his life choices. It’s a world that presents him with familiar faces, from elevator run-ins with mistresses of past affairs to attorneys retained for past divorces. But it’s also a world that brings him to similar life crossroads, opportunities to make a change for the better or to make the same mistakes that lead to his current situation. In the moment, it is difficult for him to realize which choice will lead to the better outcome, and which will just lead him back to where he started. As Pete asks Don during their car ride, “You think you’re going to live your life over and do it right, but what if you never get past the beginning again?”

That’s the best I can do to contextualize the odd storyline of Don and Diana the waitress. Don has his job back and has made millions of dollars through the acquisition by McCann. But his greatest life worries – that he never did anything, and that he doesn’t have anyone – are becoming closer to a reality for him. He stares jealously at Betty and Henry in the kitchen with the sons he only sees every other weekend. He doesn’t see his daughter, who is off at boarding school. His divorce from Megan has been long, exhausting and expensive. She later tells him that he is an aging, sloppy, selfish liar, and he does not fight back, because he knows that each one of those accusations is true. Nothing, she says, about Don is real – and he knows it.

So for whatever reason, he sees his chance at having something and someone truly real in a waitress that he finds in a diner and later finds himself with at her crappy apartment. They share their stories of divorce and of children and of grief and of pain. He told her last week that he believes that he knows her, and perhaps that it is because he is assuming that he knows what she needs and that he can provide her with whatever that is. Perhaps he confuses his feelings for Diana with his feelings for Rachel, and his attempt to have something with Diana is merely a way for him to achieve his “life not lived” with the former Ms. Menken.

But just when the episode teetered on the brink of cliché – of Don once again presenting a ring from a former Mrs. Draper to a dark-haired woman he barely knows, and of him naively pursuing a road that he believes will lead him to happily ever after – Diana stops him. “Can’t you see I don’t want anything?” she asks. He tells her he has done this before, and that he is ready to go with her, but she isn’t interested in going there with him, wherever “there” is. He offers her a guidebook of Manhattan and offer to move in and up with him, but she knows that’s an empty bargain. “You’re fooling yourself,” she tells him, “if you think this will make a difference.”

She is right. Who is Don to offer anyone any type of guidance? And as Don learns in the next scene, when he returns to his expensive but empty Upper East Side apartment, now missing examples of his wealth and Megan’s touch, his invitation was just as hollow as Diana perceived it to be. Diana also tells Don that she can’t be with him because she doesn’t want to feel anything other than the feeling she has of missing her daughter. Don makes her forget her daughter, and that’s something she won’t allow herself to do.

And hopefully, that is something Don won’t let himself do either. Rather than repeating the mistake of his past by always trying to find happiness in starting something new, Don needs to move forward by building on whatever it is that he has. Don’s daughter, Sally, has been the most glaring omission through the season’s first two episodes, and the show needs to correct that. With Megan flying back to L.A. a million dollars richer and Betty seemingly happy with her life with Henry, Sally is the one (young) woman in Don’s life that offers him the best chance at what he is looking for. With 87 episodes in the books and only five yet to come, viewers do not have the patience or emotional capital available to spend on Don looking for happiness between spread legs in dark alleys behind diners. They know his best chance at being happy is driving up to the boarding school to see Sally, taking his daughter to dinner and joking about skipping out on the check.

When Don and Betty inform their children during the Season 3 finale that they are divorcing, Don tells Sally “I will always come home.” Don has put his daughter through hell since then, but it’s finally time for Don to follow through on that promise. It is, perhaps, the show’s only chance to have a feel-good ending fit for a Disney story.


– This week’s episode was directed by Michael Uppendahl, who has now directed 11 episodes of the series. He directed Season 5’s “The Codfish Ball”, in which Megan’s family visits New York and Roger and Marie first meet. There are many similarities between that episode and tonight’s, including copious French subtitles and mass boredom for the many viewers who have no interest in Megan and her family.

– In addition to milkshakes, wedding rings and Disneyland, there are many tips of the cap to the West Coast in this episode. Meredith and Harry discuss how tiring it is to travel to and from LA. Diana makes reference to possibly moving to San Francisco. Most noticeably, the dress Megan wears to her lunch with Harry is the same she wore when picking up Don at LAX last season – perhaps a symbol of how her life in Hollywood has not progressed much over the past year.

– The “Manson family” reference made by Don’s secretary could have been a nod to the popular internet theory that Megan was Sharon Tate or a similar victim of the killers in late 1960s Los Angeles.

– Roger makes reference to not being invited to golf with Derby Foods because Burt Peterson is head of the account at McCann. Roger has fired Bert twice – first in the Season 3 premiere, and then again after the SCDP merger with CGC in Season 6 – so it’s understandable why there is some bad blood there.

– Betty says she’s thinking of enrolling at Fairfield for a masters degree in psychology. She spent much of Season 1 seeing a psychiatrist and even spent a few sessions with Sally’s child psychiatrist in Season 4. For what it’s worth, she got her undergrad degree in anthropology at Bryn Mawr, but presumably didn’t use it much since she went into modeling after college.

– Don was likely not thrilled with the idea of golfing with clients, as the country club life has never been one he has been comfortable in. In Season 2, he leaves Betty and the kids at a Memorial Day luncheon at a Westchester County club. In Season 3, he is disgusted by Roger and Jane’s Derby Day party. Jim Cutler taunted Don last year by calling Don “a football player in a suit,” but the series has never given much indication that Don is any type of athlete.

– In sports news, it’s clear this week that Don has kept Lane Pryce’s Mets pennant, as it is hanging in Don’s corner office. By skipping from July 1969 to April 1970, the series skipped over the Mets’ 1969 World Series title of the Orioles. Don also makes reference to the New York Jets, when Megan tells him the cost of the movers. In 1970, the Jets were preparing for their first season in the NFL, which had just merged with the AFL.

– The show gave so much screen time to art director Stan Rizzo that I thought they were setting him up to be fired or leave the agency, much like how they portrayed Ken Cosgrove last week. Stan is a favorite character, but his departure would pave the clearest path for the one original character who hasn’t been seen since his Season 3 dismissal: Sal Romano.