The album is split into two distinct halves; the first half of the album features electric instrumentation, in which on side one of the original LP, Dylan is backed by an electric rock and roll band. The second half features mainly acoustic songs. The album abandons the protest music of Dylan's previous records in favor of more surreal, complex lyrics.

Some critics and fans were not quite as taken with the album as a whole, relative to his previous work, for its lack of humor or musical diversity. Still, The Times They Are a-Changin' peaked at No. 20 on the US chart, eventually going gold, and belatedly reaching No. 4 in the UK in 1965.

The album consists mostly of stark, sparsely arranged ballads concerning issues such as racism, poverty, and social change. The title track is one of Dylan's most famous; many feel that it captures the spirit of social and political upheaval that characterized the 1960s.

The Times They Are a-Changin' is the third studio album by the American singer-songwriter Bob Dylan. It was released on February 10, 1964, through Columbia Records. Whereas his previous albums, Bob Dylan (1962) and The Freewheelin' Bob Dylan (1963), combined original material and cover songs, this was the first to feature only original compositions.

Throughout 1963, Dylan worked on a novel and a play. A number of publishers were interested in signing Dylan to a contract, and at one point, City Lights (a small but prestigious company specializing in poetry) was strongly considered. However, as Dylan worked on his book at a casual pace, his manager, Albert Grossman, decided to make a deal with a major publisher.

Despite the album's thematic shift, Dylan performed the entirety of Another Side of Bob Dylan as he had previous records – solo. In addition to his usual acoustic guitar and harmonica, Dylan provides piano on one track, "Black Crow Blues". Another Side of Bob Dylan reached No. 43 in the United States (although it eventually went gold), and peaked at No. 8 on the UK charts in 1965.

Another Side of Bob Dylan is the fourth studio album by the American singer and songwriter Bob Dylan, released on August 8, 1964, by Columbia Records.
The album deviates from the more socially conscious style which Dylan had developed with his previous LP, The Times They Are A-Changin' (1964). The change prompted criticism from some influential figures in the folk community – Sing Out! editor Irwin Silber complained that Dylan had "somehow lost touch with people" and was caught up in "the paraphernalia of fame".

The Freewheelin' Bob Dylan reached number 22 in the US (eventually going platinum), and became a number-one album in the UK in 1965. In 2003, the album was ranked number 97 on Rolling Stone's list of the "500 Greatest Albums of All Time". In 2002, Freewheelin' was one of the first 50 recordings chosen by the Library of Congress to be added to the National Recording Registry as "culturally, historically, or aesthetically significant".

The album featured several other songs which came to be regarded as among Dylan's best compositions and classics of the 1960s folk scene: "Girl from the North Country", "Masters of War", "A Hard Rain's a-Gonna Fall" and "Don't Think Twice, It's All Right".
Dylan's lyrics embraced news stories drawn from headlines about the ongoing civil rights movement and he articulated anxieties about the fear of nuclear warfare. Balancing this political material were love songs, sometimes bitter and accusatory, and material that features surreal humor. Freewheelin' showcased Dylan's songwriting talent for the first time, propelling him to national and international fame. The success of the album and Dylan's subsequent recognition led to his being named as "Spokesman of a Generation", a label Dylan repudiated.

The Freewheelin' Bob Dylan is the second studio album by the American singer-songwriter Bob Dylan. It was released on May 27, 1963, through Columbia Records. The record marks the beginning of Dylan's writing contemporary lyrics to traditional melodies. His debut album Bob Dylan contains only two original songs, whereas eleven of the thirteen songs on Freewheelin' are Dylan's compositions. It opens with "Blowin' in the Wind", which became an anthem of the 1960s, and an international hit for folk trio Peter, Paul and Mary soon after the release of the album.

Dylan met John Hammond at a rehearsal session for Carolyn Hester on September 14, 1961, at the apartment shared by Hester and her then-husband, Richard Fariña. Hester had invited Dylan to the session as a harmonica player, and Hammond approved him as a session player after hearing him rehearse, with recommendations from his son, musician John P. Hammond, and from Liam Clancy.

The album did not receive much attention at first, but it achieved some popularity following the growth of Dylan's career, charting in the UK three years after its release, reaching No. 13.

Bob Dylan is the debut studio album by the American singer-songwriter Bob Dylan, released on March 19, 1962, by Columbia Records. The album was produced by Columbia talent scout John H. Hammond, who had earlier signed Dylan to the label, a controversial decision at the time. The album primarily features folk standards but also includes two original compositions, "Talkin' New York" and "Song to Woody". The latter was an ode to Woody Guthrie, a significant influence in Dylan's early career.

Oh Mercy is the twenty-sixth studio album by American singer-songwriter Bob Dylan, released on September 12, 1989, by Columbia Records. Produced by Daniel Lanois, it was hailed by critics as a triumph for Dylan, after a string of poorly reviewed albums. Oh Mercy gave Dylan his best chart showing in years, reaching No. 30 on the Billboard charts in the United States and No. 6 in Norway and the UK.

Pat Garrett & Billy the Kid is the twelfth studio album and first soundtrack album by American singer-songwriter Bob Dylan, released on July 13, 1973, by Columbia Records for the Sam Peckinpah film Pat Garrett and Billy the Kid. Dylan himself appeared in the film as the character "Alias". The soundtrack consists mainly of instrumental music and was inspired by the movie itself. The album includes "Knockin' on Heaven's Door", which became a trans-Atlantic Top 20 hit.