Today, Bob Dylan turns 75 years old. It’s a celebration not just of the man, but of his work, an enormous catalogue of incredible songs and albums. His music helped name Rolling Stone magazine, and he was inducted into the Rock and Roll Hall of Fame in 1988, the same year as The Beatles, The Beach Boys, and The Supremes. He’s sold over 35 million albums in the U.S. alone. His legacy in popular music is beyond established.
As a successful musician for over 50 years at this point, it’s understandable that younger generations that didn’t grow up with Dylan’s music wouldn’t be quite as familiar with him. And with hundreds upon hundreds of songs in his massive discography, getting into him could be a little daunting. So here are ten great, classic Bob Dylan songs for anyone interested in discovering his music to start with!
1. Like a Rolling Stone
It’s almost impossible to have a Bob Dylan list without it. It’s become the Dylan song. It’s the basis for Rolling Stone’s name, and in their list of the 500 Greatest Songs of All Time, no matter how often it gets updated, it’s number 1. It plays a crucial role in Dylan transitioning from strictly acoustic folk to adding electric guitar.
But even with electric instruments, Dylan’s folk sensibilities and emotive storytelling shine through. The lyrics tell the tale of a young rich girl and her fall from grace, a far cry from the upbeat love songs that were ruling the charts. Still, the song thrived and peaked at number 2 on the Billboard Hot 100, a remarkable feat for a song that’s over 6 minutes long.
Bob Dylan didn’t necessarily invent the protest song, but his name is what comes to mind when it’s said. Dylan’s protest songs weren’t just his early work, as evidenced by this 1975 classic and fan favorite. The track is based on a true story about Rubin “Hurricane” Carter, a boxer who was in jail for murder. Dylan read “The 16th Round,” a book that said Carter was innocent and the case racially motivated. He was inspired to write this epic, lyrically dense with accusations of institutional racism.
The song reached the top 40 of the Billboard Hot 100, a big part of his 1975 renaissance, and helped spark outcry about Carter’s imprisonment. It turned out Dylan wasn’t the only one suspicious of the motives that led to Carter being found guilty – in 1985 his conviction was overturned.
3. Tangled Up in Blue
The other song that charted well for Dylan in 1975, Tangled Up in Blue is often seen as a high point in Dylan’s lyricism. The Telegraph went so far as to call it “the most dazzling lyric ever written.” Much of the story is extremely personal, with clear references to his crumbling marriage to his wife at the time, Sara Lownds (more on her later). Dylan’s ability to bring out big emotions from small, realistic stories shines as brightly as ever on this track.
4. The Times They are a-Changin’
Perhaps the definitive protest song of its era, broad in its message with a memorable tune. Written in the middle of the Civil Rights Movement, the song is unique in its premise. It’s a protest song that’s less a call to arms, and instead a letter to older generations, to the politicians, writers, and parents of the world to get with the times. The Times They Are a-Changin’ is Dylan saying that the social progress of the times could not be stopped no matter what they did, and that the best thing for opponents of the movement to do would be to simply accept that, as the title says, the times are changing.
5. Desolation Row
This song is from the album “Highway 61 Revisited,” notable for Dylan going electric. Desolation Row, however, is the acoustic closer to the album. Whereas many Dylan songs tell stories, Desolation Row is more poetic, loose narratives dense with references and surreal imagery. The track has become a favorite among Dylan fans. It’s also an incredible commitment, coming in 11 minutes and 21 seconds long. But those who are willing to give it that time get classic Dylan in beautiful lyricism and gentle guitar work.
6. Blowin’ in the Wind
Dylan may have been a young man when he wrote this song, but the philosophical queries he asked in the form of a protest song have lived on for decades, seen as all time great lyrics. Abstract and absurd questions like “How many times must a man look up before he can see the sky?” are coupled with clear allegories of oppression, such as “How many ears must one man have before he can hear people cry?”
Released in 1963, this is one of the defining songs of Dylan’s career. It helped establish him not just as a popular artist, but as a pioneer of the protest song. The song has been referenced in works such as “The Hitchhiker’s Guide to the Galaxy” and “Forrest Gump.”
7. Subterranean Homesick Blues
One of the few songs from the 60s that’s synonymous with a video, SHB was featured as the opening of a documentary entitled “Don’t Look Back.” In it, Dylan holds cue cards with phrases from the song, matching them up with the song. One of his first electric songs, there’s a clear blues influence in the guitar, while the dense lyricism has incredible pace and internal rhymes that wouldn’t be seen regularly in music until the rise of hip-hop.
8. Don’t Think Twice, It’s All Right
After 7 songs filled with politics, protest, and wall-to-wall lyrics, this is a refreshingly simple song. It’s just Dylan, his acoustic guitar, and his harmonica. His subtle storytelling shines again, detailing the end of a relationship from a first-person perspective. With beautiful guitar playing and a mournful voice fitting the resigned acceptance of the lyrics, it’s no wonder this is one of his most popular songs.
9. Just Like a Woman
Another example of Dylan getting the most out of simple melodies, this song is an ode to femininity and a woman who exemplifies it. It’s been speculated for years who the song is about, with possibilities including Joan Baez and Edie Sedgwick. The song peaked at number 33 on the Hot 100, one of several hits from Dylan’s critically adored album “Blonde on Blonde.”
Remember when I said we’d get back to Sara Lowndz? Their marriage continued to crumble into the mid-70s, when they became estranged. “Sara” was Dylan’s last-ditch plea to win her back. He was so desperate that in fact, he tried to win her back with this song while recording it – she was on the other side of the glass, watching. Reports of her reaction vary, but the one that’s gained the most traction was from Jacques Levy, who co-wrote some songs with Dylan and said “It was extraordinary. You could have heard a pin drop… She was absolutely stunned by it.” Though a standout track that potentially won her over, the marriage officially ended in 1977.
If you think other, more underrated Dylan songs deserved a place on this list, share them in the comments!