Bob Dylan's Best Songs

Bob Dylan's Ten Best, Influential Songs

From gospel to rock, country to soul... Bob Dylan's catalog of music is quite extensive and versatile. It can be difficult to know where to start when you're just getting to know his work. So, in the interest of cutting to the chase, here are ten of Bob Dylan's best songs for your introductory Dylan playlist. (See also Bob Dylan's Best Albums.)

"Maggie's Farm" (from 'Bringing It All Back Home', 1965)

Bob Dylan - Bringin It All Back Home
Bob Dylan - Bringin It All Back Home. © Columbia

Bob Dylan's work has often proven to be the sonic equivalent of a patchwork quilt. Pulling together elements of folk, blues, and rock and roll, "Maggie's Farm" is unquestionably one of Dylan's most timeless and universal "protest" songs. It's widely read as a protest song against protest songs—few things could possibly be more Dylanesque.

"Don't Think Twice, It's Alright" (from 'The Freewheelin' Bob Dylan', 1963)

Bob Dylan - Freewheelin Bob Dylan
Bob Dylan - Freewheelin Bob Dylan. © Columbia

This is quite possibly one of the best breakup songs ever written, from his landmark album The Freewheelin' Bob Dylan. And, it's just vague enough that it's hard to tell whether he was left, or whether he did the leaving. It can apply to either situation, coming across as either bitter or carefree, depending on what the listener brings to their listening experience. If Bob Dylan does anything as a songwriter, he recognizes the two-way relationship between songwriter and audience and uses it to the songs' advantage.

"The Times They Are A-Changin'" (from 'The Times They Are A-Changin', 1964)

Bob Dylan - The Times They Are A-Changing
Bob Dylan - The Times They Are A-Changin. © Columbia

Not only does this song stand up as one of Dylan's best-known tunes, but it's also one of the great generational anthems. While it speaks soundly and clearly for the Baby Boomer generation, its lyrics can easily apply to every generation as it comes of age, seeking to distinguish itself from the generation before. It's a song about the inevitability of change and, as such, perhaps, a comment about each generation's desire to "change the world." According to these lyrics, perhaps, the world just changes.

"Desolation Row" (from 'Highway 61 Revisited', 1965)

Bob Dylan - Highway 61 Revisited
Bob Dylan - Highway 61 Revisited. © Columbia

The great thing about songs like "Desolation Row"—and, perhaps, the best thing about so much of Dylan's work—is that you can listen to it over and over again, gathering new meaning each time. This is one of Dylan's finest commentaries on American culture: celebrity worship, isolation, and desperation...among other things.

"Masters of War" (from 'The Freewheelin' Bob Dylan', 1963)

Bob Dylan - Freewheelin Bob Dylan
Bob Dylan - Freewheelin Bob Dylan. © Columbia

Bob Dylan's protest song period was comparatively short, but he managed to squeeze into those few years some remarkable commentary. "Masters of War" could be one of the greatest anti-war songs of the period. In fact, it could be argued that Dylan soon stopped writing protest songs because he'd already nailed all the topics that needed discussing.

"You're Gonna Make Me Lonesome When You Go" (from 'Blood on the Tracks', 1975)

Bob Dylan - Blood on the Tracks
Bob Dylan - Blood on the Tracks. © Columbia

"You're Gonna Make Me Lonesome When You Go" is one of Dylan's most earnest love songs. Skipping right past the poetry of romance, it nails the more human, realistic aspects of the early days of a love affair. He sings about being surprised by love, humbled, and worried about the eventual but likely end. The result is possibly one of the more honest love songs in modern music.

"Like a Rolling Stone" (from 'Highway 61 Revisited', 1965)

Bob Dylan - Highway 61 Revisited
Bob Dylan - Highway 61 Revisited. © Columbia

"Like a Rolling Stone" is one of the greatest anthems of independence, individualism, and youth in modern music. The verses are overwrought with somewhat cryptic poetic imagery, the choruses are carefree declarations. Once again, leaving the true meaning of the song up to what the listener brings to the table, this song could sound like envy or mockery.

"Blowin in the Wind" (from 'The Freewheelin' Bob Dylan', 1963)

Bob Dylan - Freewheelin Bob Dylan
Bob Dylan - Freewheelin Bob Dylan. © Columbia

Songs don't quickly and easily enter the American songbook very frequently. "Blowin' in the Wind," however, is one of those songs which so completely encompasses a moment in American history while posing questions that are timelessly poignant. It became an anthem of sorts during the Civil Rights movement and stands to this day as one of the greatest songs in contemporary music.

"Hurricane" (from 'Desire', 1976)

Bob Dylan - Desire
Bob Dylan - Desire. © Columbia

Bob Dylan co-wrote this song with Jacques Levy. Telling the story of prizefighter Rubin Carter, who was framed for a gruesome murder, "Hurricane" is a song about institutionalized racism, desperation, and injustice. It's terrifically concise narrative reads like a newspaper article but bites much harder. The storyline can be hard to follow if you don't listen closely—a nice trick on Dylan's part to engage the listener in the song.

"Just Like a Woman" (from 'Blonde on Blonde', 1966)

Bob Dylan - Blonde on Blonde
Bob Dylan - Blonde on Blonde. © Columbia

Yet another great breakup tune, "Just Like a Woman" is a scathing song full of hurt and bitterness. Moving slowly through all the resulting emotions, Dylan lands on the hope of making friends, after all is said and done. It's far less cryptic than "Don't Think Twice," but no less memorable.