I loved this series from start to finish. I loved the ending, which was just right and not at all a “fuck you” IMO. I even loved the false ending and “Dear Reader” letter. Here’s my take, for what it’s worth:
Roland as a character is all about the destination. He has always been. When we first meet him, he is the kind of cold-hearted son of a bitch who will let a little boy fall to his death to continue a single-minded pursuit of a goal of questionable value. He develops relationships - with Cuthbert, with Allain, with Susan Delgado, and eventually with Jake, Eddie, Susannah, and even Oy - and it’s not that he doesn’t care about them. He does, and does so more and more over time. But it’s never about them. It’s never about the interesting places he visits, or the connections he makes, the meals he eats, or the people with whom he shares those meals. It’s about the Tower. Roland’s entire existence is an inexorable march toward a destination - the Tower - and pushing toward that destination is the single most important thing.
The Horn of Eld is a good example. It wasn’t just “a horn.” It was the horn of Roland’s fathers, first off. It was also, and more importantly, the possession of his friend, Cuthbert, killed in battle. A sentimental man, a man who feels ties to those in his life that are more important to him than his destination, would have retrieved that horn from Cuthbert’s body - as a way of bringing a connection to his friend with him along the way. But the Roland we meet is not that man. He can’t stop in his relentless deathmarch toward the Tower, not even for the ten seconds it would take to pick up a horn.
I think what King wants his book to say is that this is a self-destructive and, ultimately, fruitless approach to existence. The false ending of The Dark Tower is the “real life” ending, in a sense. No one knows what’s behind that door. Behind that door even imagination is powerless. It could be heaven, or oblivion, or something that no one even has words for. But the false ending is all that we can really have, in our existences: we open the door, and what comes after is an open question.
But King knows that his reader, like Roland, is interested in the destination. We have to have somewhere to go, somewhere to end. We’re all Roland, in the end -
we keep pushing forward, fighting to get closure that doesn’t exist. As long as we are alive, we’ll never see what’s at the top of the Tower; we’ll never get everything tied up in a little bow.
I think King is trying to suggest that existence gains its meaning from the things that happen along the way - the fights and food and sex and above all human relationships - not from pursuing ultimately arbitrary goals for their own sake.
But Roland doesn’t get this. He arrives at the Tower, but alone. Without even the horn of his best friend. But he has learned his lesson - he knows that the people who have touched his life have more meaning than the Tower itself. He calls out their names as he comes. Roland gets it.
But it’s not that simple. He still has to live it out - to actually experience existence for its own sake - before he can get a look at what comes next. So he goes back. But this time, he has the horn. We know that this time through the timeline, he cared enough about his connection to Cuthbert to pause in his path toward the Tower to pick up that horn and keep it. We can intuit that this time, perhaps, he won’t let Jake fall, will value his connections to others for more than their assistance in his trip to the Tower.
In short, the best way to get where you’re going is to stop caring so much about where you’re going.
It’s a nice theme, I think, and one that the book series delivers admirably.