There’s a bold and incredibly moving moment at the end of S07E07 (“Waterloo”) in Mad Men. Bert Cooper is dead. He died watching the moon landing; the last act of a man who belonged to the old world checking out just as the new one arrived. The next morning Don Draper is walking back to his office and Bert is there in argyle socks, no shoes, flanked by dancing secretaries, and he sings “The Best Things in Life Are Free.”

It’s one of the strangest things the show ever did. Mad Men was built on human specificity and period realism but all abandoned for a full musical number. In Don’s mind this was probably a split second; fleeting association, Bert dead, the moon on the screen, a song about the moon.

The first words out of Bert’s mouth: “Don, my boy.”

I’ve thought about those words since I first saw the episode 12 years ago and they are still deeply affecting on rewatch. Don Draper—Dick Whitman—never had a father who spoke to him with tenderness. Archie Whitman was violent and cold. Every father figure in Don’s life either hurt him or disappeared. Bert Cooper was the one man who knew the truth about Don and chose him anyway. When Pete Campbell tries to expose Don, Bert responds with “who cares?”.

Not only an act of dismissal, Bert offered Don the most radical act of acceptance he’d ever received from a man. So when Bert’s ghost opens with “my boy” it carries all of that history. It is a father figure reaching across death to claim someone.

The song itself is a quiet demolition. Don Draper is a man who sells belonging, who packages it and puts a price on it. His entire career and his entire identity is built on the proposition that the best things in life cost something and that happiness lives on the other side of a purchase. He applied this logic to himself. He bought a new name. He performed and transacted his way into respectability and into marriage and into the upper-middle class. When Bert sings that the best things in life are free it is not a platitude but an indictment on the premise Don molded his entire life on. Bert always saw past it.

The song moves from the cosmic to the intimate (“The flowers in spring, the robins that sing”) and in that narrowing it finds the precise shape of Don’s wound. These small things require presence and you have to be still to notice them.

The song eventually arrives at its core message for Don—love can come to everyone. This is the line that makes him smile and then collapses him. Don knows he can be loved but he cannot hold it, cannot trust it, and cannot feel worthy of it. For one split second Don glimpsed a worldview where none of his striving mattered and where the things he actually needs have been available the whole time and Dick Whitman was never excluded from any of it.

It takes him seven more episodes to truly absorb the message.

There is a moment in Mike Leigh’s 2014 film “Mr. Turner” that does something remarkably similar with fewer resources. Turner’s father—his assistant, companion and the quiet constant in his life—is dying and his last words, delivered with a smile, are “my little lad”. Turner is a man in his fifties and one of the greatest painters who ever lived. His dying father still sees the child. Still reaches for this diminutive, tender claim.

Leigh does what Weiner does—letting the smallness of the words carry the enormity. A dying man smiling at his son and calling him what he called him when he was small and the effect is the same devastation as Bert’s words to Don because the words “my boy” and “my little lad” are doing the same work. They are a claim of kinship offered without condition.

Now a father, I hear both of these words and I feel them pulling in two directions; as the child who wants to hear them and as the father who gets to say them. Words that Don never heard from anyone until a ghost sang them. Words that Turner heard his whole life and then never again.

I am on the giving side of that equation now and I’m recognizing words that cost nothing but will outlast anything else I’ll ever build.