Ranking Bob Dylan’s 5 Best Album-Opening Songs

Through the years, Bob Dylan has been fearless about changing up his musical approach. As a result, each album brings with it a new, unexpected experience. The first song of each album generally provides an indication about whatever novel musical direction he’s headed.

We wanted to go with some unheralded choices, but there are five Dylan album-openers that are so iconic they’re simply impossible to deny. With apologies to wonderful songs like “Hurricane,” “Love Sick,” “Thunder on the Mountain,” and several others, here are the five Dylan opening songs that, in our opinion, stand a notch above the rest.

5. “Blowin’ in the Wind” from The Freewheelin’ Bob Dylan (1963)

Anyone who heard Dylan’s debut album of mostly covers was probably floored when they put The Freewheelin’ Bob Dylan on the turntable for the first time. “Blowin’ in the Wind” is the first thing that they heard, a song brimming with such common-sense wisdom that it had to have seemed like something that Dylan had unearthed from an old folk anthology. But that wasn’t the case, because he had written this timeless creation, and at a ridiculously young age to boot. As the rest of Freewheelin’ played on, those listeners likely realized pretty quick the first song was no fluke.

4. “Like a Rolling Stone” from Highway 61 Revisited (1965)

By the time Highway 61 Revisited was released, “Like a Rolling Stone” had already been unleashed upon the world as a single, so audiences were already prepped somewhat for what they were about to hear. Truth be told, the song sounds as if it was somehow recorded a little bit different from the rest of the album. There’s a bit of haze in the atmosphere, while other songs on the record have a live-wire directness to them. Nonetheless, the song’s lyrical tone is very much in keeping with the rest of the record, which forced pop music into upheaval whether it was ready for it or not.

3. “The Times They Are a-Changin’” from The Times They Are a-Changin’ (1964)

Because he’s Bob Dylan, we tend to ascribe almost supernatural qualities to his work. Most likely, The Times They Are a-Changin’ was just the next batch of songs and a natural progression. Still, listening to that record, as song after song hits harder and harder, even in the spare acoustic-guitar and vocal arrangements, it almost feels like Dylan already knew that his music was soon going to be changing drastically. If this were the last of the so-called “protest” material, why not do it better than anybody else ever had, with the title track as the perfect tone-setter?

2. “Subterranean Homesick Blues” from Bringing It All Back Home (1965)

The title of Bringing It All Back Home was Dylan’s sly reference to the notion he was going to take rock and roll back from the Brits that had been all over the radio with it in the previous few years. When Dylan got a hold of the genre, he transformed it way beyond recognition. On the surface, “Subterranean Homesick Blues” is an effective homage to Chuck Berry. But the lyrics went to another place, somewhere where frustration is the endgame no matter which path you choose, and the recognition of that hard truth is its own kind of victory.

1. “Tangled Up in Blue” from Blood on the Tracks (1975)

“Tangled Up in Blue” was an ingenious way for Dylan to start off his bummer masterpiece, because it starts at the end of the story. The couple are already split in two, even as he pledges to get back to her somehow, someway. We then proceed to the rest of the songs, which tell us, in their elliptical, misdirectional way, what happened to bring us to that point. Aside from the apropos nature of it as a starter, “Tangled Up in Blue” is also stunning on its own, a sterling set of lyrics given one of the most passionate vocal performances of Dylan’s career.

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