The Bob Dylan Lyric that Turns from a Loving Conversation to a One-Sided Lament

Bob Dylan was only 22 years old when his third album, The Times They Are a-Changin’, was released in 1963. That’s important because he reached such a high-water mark at a ridiculously young age, pulling off incredible feats of songwriting that many other veterans couldn’t dream of achieving.

Case in point: the stunning, forlorn ballad “Boots of Spanish Leather.” It’s a song where you might not realize what’s happening and who’s talking to whom at first, although you’ll probably be able to sense the sorrow from the dejection in Dylan’s vocal. Once you do catch on, you’ll be blown away by the sleight of hand the then-youngster managed.

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In Your Letter

With “Boots of Spanish Leather,” Bob Dylan managed to write a song of heartbreak that was every bit as accomplished as the topical songs relating to current events and issues that were found elsewhere on The Times They Are a-Changin’. He was involved in a kind of on-again, off-again romance with Suze Rotolo around the time he was writing the songs that would comprise the album.

At one point, Rotolo traveled to Europe, which is likely where Dylan came up with the idea for “Boots of Spanish Leather.” The song tells the story of a romance that’s crumbling, doing so mostly by perusing through the letters each party was sending to the other. Maybe Dylan was getting frustrated at not being able to talk to Rotolo regularly and was worried that, during the lag between when she sent her letters from abroad and when they arrived, she was drifting away from him.

Whatever the reason, he concocted a somewhat unique song to detail his angst. The key to understanding it fully is realizing that, for at least the first two-thirds of the song, each verse represents a different letter, first hers to him, and then his to her, alternating each time.

That all changes with the seventh verse, the one starting, Oh, I got a letter on a lonesome day. At that point, the communication only comes from the narrator. The reason for that is the relationship has ended. You can easily miss this detail and still greatly enjoy “Boots of Spanish Leather.” But the song takes on a different level of depth once you glean Dylan’s impressive degree of difficulty.

Bye-Bye Boots

Dylan does an amazing job parceling out bits of information throughout “Boots of Spanish Leather,” almost like a mystery writer might hide his clues in plain sight. Indeed, once we’ve heard the song once and know this relationship is doomed to fail, some of these hints become more obvious and start to pop out of the narrative.

Much of the song is given over to a gentle argument between the two about what she might bring him back from her journey. It’s almost like two lovers playfully bantering about which of them is going to hang up the phone first. She wants to bring him something valuable, but he asks her just to come back to him unspoiled.

But as these letters keep flying back and forth, some cracks in the armor appear. She insists on giving him tangible gifts, if only because their reunion might be far off: That I might be gone for a long, long time / And it’s only that I’m askin’ / Is there something I can send you to remember me by? He starts to get frustrated: How can, how can you ask me again? / It only brings me sorrow.

That’s when the hammer falls. For only the seventh verse, the narrator speaks out to the audience, explaining the contents of her letter, the one that explains that she’s going to be gone for longer than expected, and her return time is undetermined: It depends on how I’m feelin’. When he starts to address her again in the next verse, it’s hard to say if he’s sending her another letter, or if he’s just venting about her betrayal.

In the final verse, he sums up the courage to wish her well on her journey. And he decides on Spanish boots of Spanish leather as an appropriate gift. If he can’t get what he truly wants, why not come out of this heartbreak with a souvenir? “Boots of Spanish Leather” might be a bit confusing at first if you’re trying to follow along with the letter writing. But the narrator’s broken heart comes through loud and clear.

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