There are few musicians who can lay claim to the title of greatest of all time as wholeheartedly as Bob Dylan. With an estimated figure of more than 125 million records sold worldwide, he is one of our biggest-selling musicians as well as the most acclaimed.
Starting in the 1960s, he became an icon of the folk music movement thanks to his lyricism that brought to life the social and political shifts of the counterculture movement. But being great was never enough for him. He infamously went electric in the mid-60s, to the ire of folk purists, and experimented with rock. Over the decades, he would shift his musical style many times, playing around with country, blues, and even gospel.
Dylan has won 10 Grammy Awards, an Oscar, a Kennedy Center Honor, and the Presidential Medal of Freedom. He's an inductee in the Rock and Roll Hall of Fame. In 2016, he became the first-ever songwriter to win the Nobel Prize for Literature. And he’s still going. In 2023, he released Shadow Kingdom, his 40th studio album, and he's still touring worldwide.
Last year saw the release of A Complete Unknown, a biopic of Dylan’s early days in the Greenwich Village folk scene, directed by James Mangold and starring Timothee Chalamet. It received eight Oscar nominations, including Best Actor for Chalamet, and brought Dylan back to the forefront of pop culture, introducing him to a new generation.
Dylan remains one of the most fascinating and enigmatic figures in music. His lyrics are often raw and revealing but he’s a deeply private man who has avoided talking to the press and being a celebrity as much as he possibly can. Many people have tried to crack the Dylan code over the decades, leading to dozens of books that seek to find answers to the many questions his songs pose. If you’re eager to become a student of Dylan-ism, here are 10 books to help you on your freewheelin’ way.

Why Bob Dylan Matters
Dylan is an icon, but it's not uncommon for some to claim that he's overrated or doesn't deserve his mighty legacy. After his Nobel Prize win, those questions became even louder. Did he really deserve the most prestigious literary prize on the planet for being a songwriter? In Why Bob Dylan Matters, Harvard Professor Richard F. Thomas answers this question with a resounding "yes".
A world expert on Classical poetry, Thomas was initially ridiculed by his colleagues for teaching a course on Bob Dylan alongside the likes of Homer and Ovid. Now, he's one of the leading “Dylanologists” in academia. His book is a distillation of the Dylan 101 course he taught, as well as a case for why Dylan is as much an era-defining poet as he is a rock and roll legend.

The Ballad of Bob Dylan
Through the lens of four seminal concerts in Dylan's career, poet and biographer Daniel Mark Epstein offers a rich portrait of the singer and his influence. Beginning with 1963’s Lisner Auditorium concert in Washington, D.C., Epstein details how Dylan went from coffee bar guitarist to the kind of musician who headlined Madison Square Garden in the '70s. Epstein also reveals how Dylan revived his flagging career in the late 1990s, and concludes his study with a look into Dylan's return to critical and commercial hits in the 2000s.

Down the Highway
Based on three years of research, dozens of interviews with friends and associates of Dylan, and documentary footage from previous decades, Down the Highway is more than just another Bob Dylan biography. Howard Sounes brings the extensive research and eye for detail that he used to write celebrated biographies of Lou Reed and Charles Bukowski. It's wide-reaching, dense, and delves into parts of Dylan's life that were previously unknown, like his second marriage and his brush with death in 1997 due to a serious heart condition.

Bob Dylan: American Troubadour (Tempo: A Rowman & Littlefield Music Series on Rock, Pop, and Culture)
Donald Brown provides commentary on Dylan's career from his first album to Tempest, his 2012 album that many critics heralded as a late-career masterpiece. Each chapter follows the shifting versions of Dylan, from purist folk hero to going electric to playing around with country music and his “sellout” years. Throughout it all, Dylan's place in contemporary American culture has remained undisputed.

Dylan: Disc by Disc
Disc by Disc studies each of Bob Dylan's studio LPs as of 2015: 36 releases in total. A variety of fans, critics, and experts explore each album in its full glory, tracking his growth and evolution as he experimented with new ideas and genres. Commentators included within its pages are Questlove of the Roots, Jason Isbell, Ric Ocasek of the Cars, legendary music critic Robert Christgau, and longtime Dylan pal Eric Andersen.

Bob Dylan—All the Songs
How many songs has Bob Dylan written? According to The New York Times, it's somewhere in the region of 600 (although it could be more depending on what we count.) Philippe Margotin and Jean-Michael Guesdon, who previously wrote comprehensive studies covering The Rolling Stones and Bruce Springsteen, took on the unenviable task of telling the story of every Dylan number written over six decades. They delve into Dylan's creative process, the stories behind his songs, and the contributions of countless musicians and producers who worked with him throughout his long career.

Bob Dylan in the Attic
Dylan's place in history has long been secured, but how do we understand his music through the lens of history? His songs are often deeply rooted in recounting the past, including stories of the Civil War, of 1930s labor struggles, and the seismic cultural changes of the 1960s. While Dylan was warned by his early mentor, Dave Van Ronk, that, “You’re just going to be a history book writer if you do those things", he kept exploring the past through decades' worth of music. Freddy Cristóbal Domínguez makes a provocative case for Dylan as a historian, and perhaps one of the most influential of his generation.

Another Side of Bob Dylan
Few people outside of Dylan's immediate family were closer to him than Victor Maymudes. He acted as the musician's tour manager for many years, starting in the '60s and, on and off, continuing well into the late '90s. After his death in 2001, Maymudes' son Jacob compiled this memoir from hours' worth of taped interviews.
Maymudes' first-hand account from the frontlines of Dylan's career offer an insight into life on the road. He recounts many defining events in Dylan's life, from meeting the Beatles on their first U.S. tour to his collaborations with the Traveling Wilburys to his many romances and friendships with the likes of Joan Baez and Dennis Hopper.

A Freewheelin' Time
To generations of music fans, Suze Rotolo will forever be known as the woman alongside Dylan on the cover art for his album The Freewheelin' Bob Dylan. It's one of the most iconic images of the '60s, but little was known for decades about the woman herself. In A Freewheelin' Time, Rotolo tells her story.
A politically active young artist and native New Yorker, Rotolo met Dylan when he was a rising young musician known only to the folk hero aficionados of the city. During the years they were together, Dylan was transformed from an obscure singer to a generational icon, and Rotolo had a front row seat for the drama. But it's not all about Bob. Rotolo details her own work as an artist and campaigner for civil rights, finding her voice in male-dominated spaces.

Chronicles: Volume One
We can’t recommend books on Bob Dylan without including some words by the man himself. Chronicles gives us first-hand insight into perhaps the most pivotal moments in Dylan's career, as he first arrived in Manhattan to establish himself as a folk legend. Greenwich Village of the early '60s is brought to life through Dylan's depictons of the hip happenings, musical experimentations, and friendships that defined his earliest songs. It's rare to see a public figure as notoriously opaque as Dylan open up in this manner, and he goes into unprecedented detail about his side of many oft-told stories.
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