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.


Author: R. Byrnes

Ryan is the founder and editor-in-chief of Yi! News.

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