Five favorite Bob Dylan songs

Authored By Sean Phipps

I am a huge Bob Dylan fan-which is why it has taken almost a year to figure out this list. Dylan has 46 albums listed on, and although several of those albums are considered terrible, there is still a daunting collection of immaculate songs to search through. And when you’re considering a Dylan song, the question often becomes, “OK, which version?” because he is known to completely alter the lyrics and tempo when performing live, as evidenced in the many bootlegs. The following is an incomplete list that, honestly, changes every season, depending on the weather and what version of Dylan I need at the time. Some days it’s young, politically charged Dylan, and others, it’s introspective, older Dylan, who offers his nuggets of wisdom. Here are my favorites right now.

“Girl from the North Country” (“The Freewheelin’ Bob Dylan,” 1963)
Early Dylan is full of songs about women who are far away from him. You can hear it in “Boots of Spanish Leather” and especially in “Girl from the North Country,” which is one of the saddest, most bittersweet songs I’ve ever had the pleasure of hearing. Dylan asks someone, a presumed friend, that if they’re “travelin’ in the north country fair,” would they mind just checking in on a girl who “once was a true love” of his? He then tells this person to give her a coat if she appears cold and to relay the information back to him whether her hair is still long and flowing. And then we get the gut punch in the fourth and final verse before the reprise: “I’m a-wonderin’ if she remembers me at all.” She was completely unforgettable to him, but it’s possible she doesn’t even remember him? Unbelievable.

“The Ballad of Frankie Lee and Judas Priest” (“John Wesley Harding,” 1967)
According to Allen Ginsberg, Dylan had talked to him about changing things up for “John Wesley Harding,” telling him “he was writing shorter lines, with every line meaning something. He wasn’t just making up a line to go with a rhyme anymore; each line had to advance the story, bring the song forward.” This new approach worked for Dylan, bringing us songs like “All Along the Watchtower” and “I Dreamed I Saw St. Augustine.” As a whole, “John Wesley Harding” is among my favorite Dylan albums, if only for “Frankie Lee and Judas Priest,” which I first heard performed by a camp counselor in the sixth grade. I fell in love with the strange lyrics about a poor guy named Frankie who gambles his friend’s money away and dies of thirst in his arms several verses later. Like a lot of Dylan songs, I have no idea what the lyrics mean in this one. There are morals, but what drew me in initially was that this is just a great first song to hear from an artist like Dylan. Had I heard “When Did You Leave Heaven?,” I might have stopped perusing the Dylan catalog. 

“Blind Willie McTell” (“Infidels Sessions,” 1983)
A song produced by Mark Knopfler (of Dire Straits fame), “Blind Willie McTell” was left off of Dylan’s critically acclaimed “Infidels” album of 1983. The song tells the story of legendary piedmont/ragtime bluesman Blind Willie McTell and has quickly become a classic, despite its omission from the original album. Why was it left off? Well, Dylan says it wasn’t finished early enough. His explanation is legendary: “It’s like taking a painting by Monet or Picasso-goin’ to his house and lookin’ at a half-finished painting and grabbing it and selling it to people who are ‘Picasso fans.'” OK, Mr. Dylan. Fair enough. This is one of my favorite songs because, again, the imagery of Mr. McTell’s existence. The “electric version” release is art. The minor chords make the song. 

“The Lonesome Death of Hattie Carroll” (“The Times They Are A-Changin’,” 1964)
This is one of only a handful of Dylan songs that I could play in its entirety with no mistakes if you were to hand me a guitar. It’s also one of a handful of Dylan songs that can make me weep every time I hear it. During his political activist phase, Dylan would often write songs culled from the headlines of the newspaper. “Hattie Carroll” recounts the true story of the murder of a 51-year-old black woman by a tobacco farmer in Maryland named William Zantzinger. Dylan explains in this interview how he wrote the song and plays a stunning version of it. The key to this song is the chorus: “You, who philosophize disgrace and criticize all fears, take the rag away from your face, ’cause now ain’t the time for your tears.” The verses explain how Zantzinger murders Carroll, and the judge passes a measly six-month sentence. This is the REAL reason to cry, Dylan says. The injustice of the situation is when we should “bury the rag most deep in our face.” 

“Mississippi” (“Love and Theft,” 2001)
The album “Love and Theft” was released on Sept. 11, 2001. I remember having plans to go out and get the album until, well, you know. I’ve often tried to listen to the album without remembering that day, but the thought of it always bores back into the forefront. The one exception is the song “Mississippi,” which is one of Dylan’s catchiest songs with, according to a review on, “… glimpses of a man with not-so-bitter regrets and lessons learned and accepted.” I like this Dylan. This was exactly the Dylan I needed on that day and for many days after. This song in particular is so poignantly a reminder of that day that it’s almost eerie. The first verse: “Every step of the way, we walk the line. Your days are numbered, so are mine. Time is piling up, we struggle and we stray. We’re all boxed in, nowhere to escape.” He goes on to tell us to forgive and forget everything and focus on what’s important. In this song, getting out of Mississippi is of utmost importance, but even that is tolerable. I love this song. I’ll leave you with a performance of the song from 2002.

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