5 Deep Cuts From Bob Dylan That You Should Be Listening To

There are very few people that have written as many incredible songs as Bob Dylan. And for every individual one, there is a “Dylanologist” that can quote you chapter and verse. For fans in that vein, there may not be a single song in Dylan’s more than half-a-century recording career that they don’t intimately know.

Yet, the more casual Dylan listener may only know the top hit albums and singles. To get a complete picture of one of the most masterful, yet mercurial, songwriters of all time, you need to know the best of the deep cuts, album tracks, and lost ephemera as much as you need to know the songs that made him a legend. Here are five among a long list of underappreciated Dylan songs.

1. “To Ramona” (From Another Side of Bob Dylan, 1964)

In “To Ramona,” Dylan makes multiple allusions to his relationship with fellow folk singer Joan Baez. The waltz-y track signals the iconic songwriter’s shifting interest from political anthems to more personal and intimate affairs.

Dylan and Baez split ways not only romantically but also philosophically in the mid-’60s—Baez couldn’t part from the politically conscious folk scene while Dylan split from it almost entirely. In her memoir, Baez said the two have discussed this topic openly with Dylan marking the main difference between the pair as “she thought politics could change the world and he knew it couldn’t.”

In “To Ramona,” if Baez is right, Dylan is explaining his decision to her. He expresses still being in love with her (Your cracked country lips I still wish to kiss) but they will never be able to see eye to eye (For deep in my heart / I know there is no help I can bring).

2. “You’re No Good” (From Bob Dylan, 1962)

From his oft-overshadowed folkie debut comes this bout of rockabilly. “You’re No Good” proves that even in his earliest stages, making his name in the folk scene, Dylan had rock and roll in his veins.

This song once again sees Dylan wax poetically about his love life instead of the sharp social commentary he would be putting out to great appeal later on in the decade. He starts the song by singing I don’t know why I love you like I do / Nobody in the world can get along with you before closing things out by ceding Well, you give me the blues, I want to lay down and die.

3. “Where Are You Tonight? (Journey Through Dark Heat)” (From Street Legal, 1978) 

“Where Are You Tonight (Journey Through Dark Heat)” closes out Dylan’s 1978 album Street Legal.

Dylan has said the song is about the individual’s “enemy within” while critical interpretations have suggested that it references Dylan’s divorce as well as foreshadowing his conversion to Christianity. His conversion became evident in the subsequent projects following Street Legal but before things could get steeped in religion, Dylan wanders around scarcely populated streets in this song, looking for a woman he lost somewhere along the way.

4. “Dark Eyes” (From Empire Burlesque, 1985)

Though a lot of the ’80s saw Dylan knee-deep in synth drums, he went back to the acoustic guitar for the hazy, folk number “Dark Eyes.”

In his memoir, Chronicles, Dylan wrote that this song was inspired by a meeting with a prostitute who “had a beautifulness, but not for this kind of world.” In a similar fashion, Dylan longs for a different kind of world in “Dark Eyes”—one where the earth is strung with lovers’ pearls and where time is short and the days are sweet and passion rules.

5. “Standing in the Doorway” (From Time Out of Mind, 1997)

It’s easy to forget – because of the millions of other things Dylan does so well—that he sure does write a great heartbreak song.

In “Standing in the Doorway,” everything is a bit too much for Dylan. From the too-bright lights to time running too fast or too slow, Dylan can’t catch a break. He sings You left me standing in the doorway cryin’ / I got nothin’ to go back to now.

(Photo: Bob Dylan YouTube)