Welcome to Chillers, the ongoing series where we take a look at songs that give me goosebumps. Bi-weekly posting will be done on WordPress with a cross-post to Bluesky.

An interesting song within a not-often-discussed topic, “The Night They Drove Old Dixie Down” by The Band looks through the eyes of Virgil Kane, a poor white Southerner in the waning months of the Civil War. He recalls working on the Danville train and reflects on the fall of Richmond with a sense of battered nostalgia.

Now — we have to acknowledge the uncomfortable part: referring to Robert E. Lee as “the very best.” It’s jarring, and rightly so. But within the narrative perspective of the song, it functions as an honest portrayal of someone raised within the ideology of the time. If you can separate the character’s worldview from the actual musical craftsmanship, the song stands as a testament to:

a person’s willpower, commitment to a cause (however flawed), and how historical conviction can ripple through entire family lines.

It’s haunting. It’s complex. And it’s a reminder that this song came out 100 years after the Confederacy, in an era when society still found casual comfort romanticizing its memory. That tension — between the beauty of the music and the discomfort of its context — is exactly what makes it a Chiller.