What The Most Important Song In Mad Men's Final Season Means For Don Draper

As Mad Men comes to a close, I find myself thinking about Bert Cooper's song and dance routine. That scene was whimsical and fun -- two things Don Draper is typically not -- but it has me wondering what it says about Don Draper's future.

In the episode, "Waterloo," from the final season's mid-point last year, Don had just managed to save his career, yet again, and reestablish himself as the alpha ad man at the agency, Sterling Cooper & Partners. Then, out of nowhere, there's Bert -- played by Robert Morse -- back from the dead, singing and dancing along to "The Best Things In Life Are Free," as seen through Don's eyes. Morse, a Tony Award-winning actor, sang it without the swing, imbuing the lyrics with a near-saccharin optimism, and tap-danced in his socks alongside the SCP secretaries as chorus girls.

Clearly the creative minds behind Mad Men wanted a send-off worthy of a character as integral to the series as Bert Cooper -- and an actor as accomplished as Morse. But if that was their main intention, then why not have John Slattery's character, Roger Sterling, witness the brief moment of musical resurrection? After all, Sterling and Cooper had been partners and friends long before Don Draper ever entered the picture. What message was the musical sequence intended to convey to Don?

Written by Buddy DeSylva, Lew Brown and Ray Henderson for the 1927 show Good News, a musical about a college football star who falls in love with his female tutor, "The Best Things In Life Are Free" has been covered by the likes of Dinah Shore, Frank Sinatra, and Sam Cooke -- the latter of which recorded a swing version live at the Copacabana in New York City in 1964.

The lyrics begin with a reference to the moon, which was fitting since "Waterloo" centers heavily on the famous Apollo 11 moon landing: The main characters gathered around their TV sets to witness the big event; Peggy Olson worried that a botched landing would be bad for business; and Cooper died that very night. But the song is about more than just the moon and stars. It's a reminder that the greatest things in the world can't be owned. It's a sentiment antithetical to the advertising industry, which thrives by selling the belief that buying things can make you, the consumer, happier. And it's a concept that Don Draper may finally be starting to grasp.

Earlier in the episode, Cooper admonishes Sterling for not being a leader. It is the final conversation they have before Bert's death -- and one of the most honest exchanges of the season between the two men. Bert's words present Roger with a challenge to finally grow up and take the reins of the company, a challenge that Roger ultimately meets. For Don, the only way he will ever grow up is if he can learn to truly value the best things in his life: The women who love him, his relationship with his children, and the pleasure derived from a job that allows him to do what he loves.

Let's hope he got the memo from Bert's musical performance.