Bob Dylan’s Odyssey: A Deep Dive into the Life of a Music Legend

Fans have been trying to find the right box to place Bob Dylan throughout his career, but he has continuously drifted from one style of music to another. Whether you enjoy his music or not, criticize his singing voice or feel its raw power, whether you see his words as pure poetry or mere lyrics, there is no denying that Dylan is one of the greatest and most influential artists in the world of music.

While music is his main asset, Bob Dylan also has a fascinating personality and temperament. He seems to fit exactly into that archetype of the solitary wise poet, disappearing for a while and reappearing at the right moment in order to spill some of his wisdom. He is also, by every meaning of the word, hardheaded.

Dylan started off as a folk singer in the early 1960s in New York. Right when his fans started looking at him as a folk singer, he switched to protest songs and before this label could stick, he picked up an electric guitar and sang rock and roll songs. It seems that whatever people thought Bob Dylan was and should be, he disagreed with it and found new identities to embody and new music to make. Let’s dive into Dylan’s colorful discography in an attempt to identify all of the different genres that he tried out.

In the Beginning, There Was a Folk Singer

Bob Dylan arrived in New York in 1961 at the beginning of the folk revival movement, which saw names like Joan Baez, Joni Mitchell, and Dave Von Ronk revisit the classics of folk music and breathe new life into them. They held small shows in underground cafes and pubs of the city. Dylan became known for his playing style that combined the acoustic guitar and the harmonica mixed with his raw singing voice. All of this resulted in powerful renditions of already-known songs.

In 1962, he recorded and released his first album. It was a self-titled collection of his renditions of classic folk songs with two original songs as well. The album didn’t do too well, selling only 5000 copies. His second album, however, would change his life forever. He recorded and released The Freewheelin’ Bob Dylan the following year. This album contained Dylan’s original compositions exclusively. His song Blowin’ in the Wind became an anthem of the 1960s. It was instantly endorsed by the counterculture movement of the era due to its combination of traditional melodies and socially aware lyrics. Songs like Masters of War and A Hard Rain’s a-Gonna Fall reflected the ideas and hopes of an entire generation protesting against everything they thought was wrong with American society. Dylan’s songs seemed to poetically summarize their feelings.

Bob Dylan has always been reluctant to identify his pieces as protest songs, but fans always saw them as those. While there were a couple of songs in The Freewheelin’ Bob Dylan that fans dubbed as protest songs, this status would be radically amplified with the release of his following two albums in 1964. This year, Bob Dylan accepted his duty as the poet of a generation in upheaval, and the songs he released on both albums are the most political of his entire career.

From the true and sad story of The Lonesome Death of Hattie Caroll to the strong criticisms of Only a Pawn in Their Game, Dylan sang about what his generation was fighting for and did it confidently. He traveled all around the USA, playing festivals and concerts for hundreds of thousands of devoted fans who saw him as their God.

In contrast, Dylan would attempt to escape this classification more than any other artist for the rest of his career. But as much as he tried to dodge the label of a protest singer, fans insisted on it and expected him to rise up again and write a song about new issues that came up. When he refused or couldn’t do that, they would be disappointed and call him a traitor. Put simply, Dylan was done with this stage of his career and he wanted to move on to the next one. He was never interested in doing one thing exclusively and he couldn’t care less if that made his fans satisfied or unhappy.

Bob Dylan became the face of the Newport Folk Festival, so when hordes of eager fans went to see him play at the festival in 1965, they were expecting thought-provoking, politically aware protest songs, sung with his wry voice and played on an acoustic guitar with his accompanying harmonica. To everyone’s surprise, Dylan walked onto the stage with a Stratocaster and a band behind him. He went electric.

In a legendary moment that would forever alter music history, Bob Dylan played his song Maggie’s Farm with distortion turned all the way up while the crowd booed him throughout the entire performance. Allegedly, a man even walked up to the stage and tried to cut the cables with an axe.

Still, with the same determination that he has always been known for, Dylan embraced his new identity as a rock and roll musician and released many albums that became landmarks of classic rock. In the same year, Highway 61 Revisited and Bringing It All Back Home were released. Two of his most celebrated works contained songs played on the electric guitar with a full band. Titles like Subterranean Homesick Blues, Like a Rolling Stone, and Ballad of a Thin Man saw Bob Dylan abandon his folk roots in favor of heavier tunes that embraced the psychedelic rock movement of the mid-60s in their lyricism. Lines like The man in the coon-skin cap in a pig pen wants 11 dollars, you only got 10 feel like the ramblings of a mad man, possessed by some magical power, but they earned Dylan a new and much bigger audience.

In the 1965 documentary Don’t Look Back, you can see exactly how Dylan was hailed and perceived. The concert footage from his 1966 tour in England shows hundreds of thousands of fans waiting in long queues to get a chance to see him. Everyone knew Dylan was becoming a legend.

In late 1966, Bob Dylan had his famous motorcycle accident. While the crash wasn’t severe, it still made him take a break and focus on his family. When he re-emerged in 1974, he went on a long tour with his band and played huge sold-out arenas. During the period when he was away from the stage, he still managed to release a few albums. Blonde on Blonde is arguably his best, John Wesley Harding and Nashville Skyline marked the return to his roots, while New Morning and Self Portrait served as attempts at something new and experimental.

His return to the stage was followed by a devastating divorce, which then led to two of the most beautiful but sorrowful albums—Blood on the Tracks and Desire. These albums showed the world a previously hidden side of Dylan that was tragic and vulnerable. Songs like If You See Her, Say Hello and Sara have a soft romantic touch to them but with a generous serving of the spirit of blues. These two great works of art would be followed by a few mediocre ones and a couple of hidden gems as well. In 1989 he released one of his most underrated works called Oh Mercy. 

Collaborating with U2’s producer Daniel Lanois, Dylan recorded and released an album of blues rock that would set the tone for the remainder of his career. He speaks fondly of this period in his memoir Chronicles Vol. 1 and expresses his doubts about the making of this album.

Bob Dylan’s last few albums have a mature taste to them that is dripping with wisdom. His unofficial trilogy of Time Out of Mind, Love and Theft, and Modern Times contains generally slower and longer compositions with a heavy focus on lyricism and story-telling. For example, the song Highlands in the aforementioned Time Out of Mind is a 16-minute-long exploration of many themes and personal issues for Dylan. It plays out more like a short story than a song and features a minimal bluesy guitar-and-drum instrumental and his wry, aged voice.

His latest album Rough and Rowdy Ways was released during the COVID-19 pandemic. Bob Dylan is still touring at the age of 82, and perhaps, we may still get an album or two before he calls it quits. For a man who has done almost everything there is to do in music, one can’t help but wonder what else he still has to offer.