The Freewheelin' Bob Dylan (1963)
The Freewheelin' Bob Dylan is not the first Dylan album (that honor would go to 1962's eponymous Bob Dylan), but it is the first to truly display his songwriting talents. Still quite young at 22, Dylan wrote political songs like "Blowin' in the Wind", "Masters of War" and "A Hard Rain's a-Gonna Fall."
These songs contrasted lyrically with humorous narratives like "I Shall Be Free" and "Talkin' World War III Blues." Dylan's girlfriend at the time, Suze Rotolo, is featured walking hand-in-hand with him on the album cover, and "Don't Think Twice, It's Alright" is a bittersweet send-off to her. This album began Dylan's rise to stardom.
Bringing It All Back Home (1965)
Only 2 years after Freewheelin', Dylan had become an enormous success, billed as the country's premiere folk singer and the "voice of a generation". Dylan resented the label, feeling pigeonholed by his folk singer image. With Bringing It All Back Home, he decided to crush any of those notions and, in the process, reinvented popular music forever.
The first half of the album was the acoustic songs Dylan was known for, but the second half brought a new direction. Backed by a full band, Dylan delivered his trademark vocals over rollicking electric guitar and a pulsing rhythm section. He was deemed a "sell-out" for changing his musical style. Audiences eventually warmed up to the music, and Bringing It All Back Home is now regarded as a landmark album.
Highway 61 Revisited (1965)
In a feat that remains almost unrivaled, Dylan managed to release not 1, but 2 masterpieces within the same year. The majority of Highway 61 Revisited followed the electric style from the previous album; album closer "Desolation Row" was the exception, and the epitome of Dylan's acoustic songwriting, clocking in at over 11 minutes long.
The opening snare of "Like A Rolling Stone", Dylan's most famous song, kicks off the album and remains one of the most venomous put-downs ever put down to tape. Inspired by an interview he had with Time Magazine, "Ballad of a Thin Man" has Dylan pointing fingers at the critics and journalists he felt could never truly understand his work.
Blonde on Blonde (1966)
After a whirlwind year of concerts, Dylan returned to America to record his next album, Blonde on Blonde. The songs on the record focused on love, anger, regret, and humor and were filled with the most poetic and dense lyrics of his career.
The album was also over an hour long, then an impressive feat, and divided onto two records. Dylan said that it was the only album of his which accurately captured the "thin, wild, mercurial sound" that he envisioned in his head.
Blonde would serve as the final album of the first part of Dylan's career, and is now regarded as one of his best works. After touring the album, Dylan would return to the States and seriously injure himself in a motorcycle accident. It would three years before he appeared in public, radically altering his music and image when he did.
Blood On The Tracks (1975)
By 1975, Dylan's marriage was falling apart, and while his post-1966 work had been generally well-received, it was not on the same critical level as albums like Highway and Freewheelin'. Blood on the Tracks reignited their beliefs that Dylan was in fact the genius that the '60s labeled him as.
The album focused on Dylan's complex relationship with his wife as told through atmospheric narratives like album opener "Tangled Up in Blue" and "A Simple Twist of Fate." "Idiot Wind" is an almost eight-minute long emotional tirade against his wife. "Buckets of Rain" ends the album on a positive note, but reality did not follow suit; Dylan would separate from his wife shortly after Tracks' release.