I must admit here that I, like many people I know, felt this connection fade as I got older. As my own urgency leveled out, Oberst continued to make music that was stunning and emotionally layered, but felt distant from my own needs and concerns. Listening to all of his works in order presents an interesting context that makes the journey more interesting. I first sighed as the set kicked into Digital Ash, which was the album that signaled the distance I began to feel from Oberst’s music back in 2005. Now, though, with an entire era of music at my disposal, it is a more endearing and challenging listen — one that reminds me that Oberst, too, was once young and then got older. In this way, he was just like all of the other young stars of his era. He had to figure out how to navigate adulthood in a way that stayed true to who he was becoming, while still carrying everyone with him. His struggle was, of course, a different one than those faced by Britney Spears, Christina Aguilera, or Justin Timberlake, but it was rooted in a similar, human fight: So often, we want our beloveds, our heroes, to stay as they were when we met them first. But we also ask them to take us with them, no matter where the journey leads. It’s something we’re not always actually prepared for, but it sounds nice.
With this in mind, I listened to both Digital Ash and Cassadaga with new ears. It sounds now like an artist with time at his back, fighting to hold on to who he is. I am getting older now, and I have long given up on denying it in the ways that I might have in 2005 or 2007. Because of this, I feel like I have no choice but to appreciate the artist who wrestles with what time asks of them, and pushes back. These two albums are still my two least favorite in the set, but they do more emotional labor than the others, which tend to wear everything across their chests in a way that is beautiful, but not as nuanced.
That is my opinion on Conor’s evolution and why I continue to support him. His first albums have very little appeal to me these days outside of nostalgia. I remember how I felt when I listened to those songs 15 years ago yet, I can’t find them relatable. It wasn’t until 2010’s albums and newer that I really feel a connection. He’s grown up and so have I.