3 Songs From Bob Dylan That Will Make You Cry

Bob Dylan is the definitive singer/songwriter with a career that has spanned six decades and hundreds of songwriting credits. Poetic, introspective, and experimental, his lyrics are held close to the hearts of many of his fans for a reason. And many of his genre-spanning songs are more than capable of making even the hardest person tear up a bit. Ready to get sad? Here are three songs from Bob Dylan that will make you cry.

1. Boots Of Spanish Leather

This classic tune from 1963 is one of Bob Dylan’s most iconic, and it’s also a pretty sad song when you look at the context and meaning behind the lyrics. It’s about two lovers who have drifted apart, and their relationship has reached its end. The narrator repeats that all he wants is to see her again, but it’s clear that she’s done.

So, at the end of the song, instead of requesting in various poetic ways for her to return home to him, he simply asks for “boots of Spanish leather” as a souvenir from her travels. Or, rather, something to remember her by, since he will likely never see her again. A true heartbreaker.

[Catch Bob Dylan Live on the Outlaw Music Festival Tour With Willie Nelson]

2. Most Of The Time

“Most Of The Time” is one of Dylan’s most interpreted songs. At its core, it’s a ballad. One could interpret the song as the aftermath of heartbreak, where the narrator feels fine “most of the time” but is still partially affected by the long-ended relationship.

Others have interpreted the song as a shining example of an unreliable narrator, as the music and the lyrics of the song contradict each other. Just as well, many believe the song is autobiographical and might be a reference to Dylan’s relationship with his ex-wife, Sara. Either way, it’s a gloomy tune that’s perfect for a sad playlist.

3. If You See Her Say Hello

This song was one of Dylan’s hits from the 1975 album Blood On The Tracks. It’s also (arguably) one of his saddest songs to date. The song is a simple yet catchy tune that describes your typical sad love story, but the narrator reflects on the ended relationship with a sense of melancholy, dignity, and fondness. It’s soft and beautiful, but also very sad. Especially if you just went through a breakup yourself.

Photo by Michael Ochs

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