Blonde on Blonde is the seventh studio album by the American singer-songwriter Bob Dylan, released as a double album on June 20, 1966,[4] by Columbia Records. Recording sessions began in New York in October 1965 with numerous backing musicians, including members of Dylan's live backing band, the Hawks. Though sessions continued until January 1966, they yielded only one track that made it onto the final album—"One of Us Must Know (Sooner or Later)".

It was voted No. 26 in the third edition of Colin Larkin's All Time Top 1000 Albums (2000) and was featured in Robert Dimery's 1001 Albums You Must Hear Before You Die (2010). "Like a Rolling Stone" was a top-10 hit in several countries, and was listed at No. 4 on Rolling Stone's "The 500 Greatest Songs of All Time" list in 2021. Two other songs, "Desolation Row" and "Highway 61 Revisited", were listed at No. 187 and No. 373 respectively on the 2010 list.

Highway 61 Revisited peaked at No. 3 on the US Billboard Top LPs chart and No. 4 on the UK Albums Chart. Positively received on release, the album has since been described as one of Dylan's best works and among the greatest albums of all time, ranking No. 4 on Rolling Stone's "The 500 Greatest Albums of All Time" list in 2003 and repositioned to No. 18 in the 2020 revision.

Preceded by the hit single "Like a Rolling Stone", the album features songs that Dylan has continued to perform live over his long career, including "Ballad of a Thin Man" and the title track. He named the album after the major American highway which connected his birthplace of Duluth, Minnesota, to southern cities famed for their musical heritage, including St. Louis, Memphis, New Orleans, and the Delta blues area of Mississippi.

Highway 61 Revisited is the sixth studio album by the American singer-songwriter Bob Dylan, released on August 30, 1965, by Columbia Records. Dylan continued the musical approach of his previous album Bringing It All Back Home (1965), using rock musicians as his backing band on every track of the album in a further departure from his primarily acoustic folk sound, except for the closing track, the 11-minute ballad "Desolation Row". Critics have focused on the innovative way Dylan combined driving, blues-based music with the subtlety of poetry to create songs that captured the political and cultural climate of contemporary America. Author Michael Gray argued that, in an important sense, the 1960s "started" with this album.

"Subterranean Homesick Blues" is a song by Bob Dylan, originally released on the album Bringing It All Back Home in March 1965. The following month it was issued as a single, becoming his first Top 40 Billboard Hot 100 hit (#39) and going Top 10 in the UK. It was subsequently re-released on numerous compilations such as Bob Dylan's Greatest Hits (1967). One of Dylan's first 'electric' pieces, "Subterranean Homesick Blues" was also notable for its innovative film clip, which first appeared in D. A. Pennebaker's documentary, Dont Look Back.

Bringing It All Back Home is the fifth studio album by the American singer-songwriter Bob Dylan, released in April 1965 by Columbia Records. In a major transition from his earlier sound, it was Dylan's first album to incorporate electric instrumentation, which caused controversy and divided many in the contemporary folk scene.

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".