By MORGAN SHELDON

1. “Desolation Row” – A tale about the town of “Desolation Row,” where the cast-off and queer can find refuge. Dylan himself has said that he has had trouble writing a song better than this, due to its lyrics already containing a small portion of every emotion a human can feel—love, longing, happiness, loneliness, hatred, contentment, etc. While this is perhaps an exaggeration, it is no overstatement that this song is undeniably one of Dylan’s best songs—if not the best—due to how well it explains the complex array of human emotions.
2. “Sad-Eyed Lady of the Lowlands” – While some consider “Visions of Johanna” to take this spot, “Sad-Eyed Lady” shows Dylan’s maturity as an artist, having come to the realization that perfection is unattainable. He is able to write about the woman he loves with just enough specificity to be impactful, yet with just enough vagueness to be whimsical & romantic.
3. “Ballad of a Thin Man” – One of Dylan’s most scathing songs, “Ballad of a Thin Man” contains Dylan’s resentment for the media of the 60s & those who didn’t understand what he did. However, even outside of this context, it is just as harrowing if you take it as a song about being angry at someone for not understanding something so simple about you.
4. “The Lonesome Death of Hattie Carroll” – Considered by Joan Baez to be Dylan’s best protest song, “The Lonesome Death of Hattie Carroll” discusses the racially-motivated death of Hattie Carroll at the hands of William Zantzinger, and the subsequent trial that ended with Zantzinger receiving only six months in prison. The song challenges the idea that all are fair in the eyes of the law, suggesting if Zantzinger was not a wealthy man who owned over 600 acres of land & knew Maryland politicians, things would have ended differently for him.
5. “It’s All Right Ma, I’m Only Bleeding” – Containing some of the best one-liners of any Dylan song—”Money doesn’t talk, it swears,” “But even the president of the United States must sometimes have to stand naked,” and “He not busy being born is busy dying” to list a few—which are indicative of Dylan’s and the general culture’s feelings towards the late 60s. It’s a song about a shared atmosphere instead of a specific thought.
6. “Queen Jane Approximately” – Very similar to “Like a Rolling Stone” & “Positively 4th Street”, “Queen Jane Approximately” is a kinder, more mature song about a lover who isn’t perfect. Sometimes love just doesn’t work out between two people, or issues arise, due to no fault of their own; to bash the other person hurts both parties, but to accept them for their flaws connects you two on a more personal level.
7. “Abandoned Love” – A song about a failing relationship that has reached its end—which makes it similar to “One Too Many Mornings” & “Boots of Spanish Leather”, though with much better wordplay and palpable emotion baked into the song instead of simply being implied. The song is not about getting one last chance, but rather just the acknowledgment that it’s time to say goodbye and move on even though you don’t know where to go.
8. “Don’t Think Twice, It’s All Right” – Something you say to yourself as you’re leaving a relationship. Sometimes you say it to convince yourself that leaving is a good idea, and sometimes you say it to the other person so as not to hurt their feelings. It’s a versatile saying, & Dylan perfectly encapsulates its meanings.
9. “My Back Pages” – One of Dylan’s first introspective songs, it seems to be his goodbye to the protest song genre of the early 60s, instead opting to write songs about his personal experiences. It is also a very apt song about learning in general, and touches upon the idea that the more you learn the less you seem to know.
10. “Stuck Inside of Mobile with the Memphis Blues” – Whether you’re physically stuck in a town you hate, or you’re more metaphorically stuck in a hard situation, this song is about your feelings. Wanting to move on, but also having a sense of nostalgia for the place you left behind; learning from your mistakes, but somehow always ending up back where you started.

Honorary Mentions (because choosing just 10 is hard): “Love Sick,” “Love Minus Zero,” “With God on our Side,” “Like a Rolling Stone,” “Mr. Tambourine Man”