How “The Best Things in Life Are Free” Gave ‘Mad Men’ Its Most Ominous Ending Yet

By  · Published on May 29th, 2014


Don Draper is losing his mind.

This is not a new theory, but after last Sunday’s season finale (for this half of Mad Men’s final season) it looks like it is becoming a fact. A season that has had Don fighting to keep everything – his job, his marriage, his family – finally allows our battered protagonist to end things on a high note with Don back on top at SC&P, letting go of a marriage that seemed only to weigh him down, and building an honest relationship with his kids (well, Sally at least).

But then the true cracks start to show.

While Don has spent the past season fighting to keep his place in his world, his world has forgotten him. Betty wants to pretend Don was just a “bad ex-boyfriend” instead of her ex-husband and the father of her three children. SC&P marched on despite Don’s forced leave of absence and while Don was certainly missed, he was never needed outright. Megan moved out to Los Angeles and started a perfectly fine, Don-less life for herself.

“Waterloo” has Don finally giving everyone what they have long been wanting from him – Peggy gets his genuine support and encouragement on taking over the Burger Chef pitch, Megan is granted release from her slowly disintegrating marriage, even Joan (who’s animosity towards Don is rooted in the money she feels he has cost her) gets an unexpected pay day thanks to Don himself. And Don seems to get exactly what he wants – to go back to work.

But in a finale marked by closure, instead of moving forward on a positive note, Don suddenly finds himself face-to-face with the recently deceased Bert Cooper.

It’s concerning enough when Don sees what appears to be a ghost, but once Bert (sock covered feet and all) starts giving Don a little song and dance to “The Best Things in Life are Free,” it is clear something is very, very wrong with Mr. Draper.

Don has always been a man searching for satisfaction, without ever finding it. He has turned himself into a rich man (even richer still thanks to this deal with McCann) who is good at what he does and has no problem finding a woman to go to bed (or to the altar) with him. But he has never been happy. The best things in life may be free, but the problem is Don doesn’t know what the best things in life are. He has never really cared about money or status, he only thinks he should, and therefore he plays the part. Being honest led him to losing his job forcing him to spend the entire season trying to get it back, not because he loves his work so much, but because it’s all he knows how to do.

Don has no problem amassing a world of material things, but finding a life full of genuine joy is something that has long alluded him. Bert never speaks directly to Don (which adds to the eerie feeling of his sudden appearance when he instead just breaks into song), but Ray Henderson’s lyrics (which Matthew Weiner hopes you listened to) say it all. Don may have gotten his life back, but is it the life he really wants or one he merely thinks he should have? An identity for identity’s sake. It is clear that something very real is still nagging at him and that nagging voice appears to him in the form of a singing and dancing Bert Cooper, a wonderful send-off for Robert Morse, but something completely out of character for Bert, and a very concerning vision for Don.

Everyone seems to have “forgiven” Don (or moved on from him) and while Bert was not Don’s biggest fan in the end, this didn’t feel like a final goodbye to give Don hope. Don has never been happy, and while he has spent the season trying to get everything back, this vision of Bert seemed to suggest that deep down, Don knows he is still not going to be happy. His honest pitch to Hershey’s in last season’s finale that led to Don being forced out of SC&P had people wondering what was wrong with him, but never bothering to get a real answer, instead simply putting him out of sight (and out of mind). In the world of Mad Men, even when someone is obviously suffering from mental ailments, no one seems to notice until something drastic happens.

Ginsberg had to cut off a nipple before his illness was noticed and Don has been battling serious demons even longer – a battle that is coming to a head as we prepare for the final seven episodes of his journey. Mr. Draper is seeing things, and these visions seem to suggest a deep unhappiness that he may not be able to overcome. In a show that’s featured grief, death and disaster, it’s the visage of a happy-go-lucky Bert that proved to be more ominous than anything else.

Now we just have to hope next season doesn’t start with Don talking about Napoleon…