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Greatest Hits presented his first appearance on records after his praised Blonde on Blonde double-LP of May 1966 and his motorcycle accident of that summer. With no activity by Dylan since the end of his recent world tour, and no new recordings on the immediate horizon (the sessions that would in part be later released as the Basement Tapes were still months away), Columbia needed new product to continue to capitalize on Dylan's commercial appeal. Hence the appearance of this package, the label's first Dylan compilation and its first LP release with a $5.98 list price, one dollar more than that of standard releases.
This album also serves as Dylan's de facto singles collection for the 1960s, as all but three of the tracks present, "The Times They Are a-Changin'", "It Ain't Me Babe", and "Mr. Tambourine Man" had been issued at 45 rpm in the United States during the decade, although "Times" made it to #9 as a single release in the United Kingdom. Peter, Paul and Mary enjoyed a huge hit with their #2 single of "Blowin' in the Wind" in 1963, and the remaining six tracks all made the Billboard Top 40 for Dylan in 1965 and 1966. A truncated rock and roll version of "Mr. Tambourine Man" had been a number one hit for The Byrds in the summer of 1965, and the Turtles took a folk-rock version of "It Ain't Me Babe" to #8 the same year. Perhaps the most astounding thing concerning this collection is that it documents a time in America when the lyric complexity and philosophic bent of "Like a Rolling Stone", "Positively Fourth Street", and "Rainy Day Women #12 & 35" could actually become top ten pop hits. "Positively 4th Street" was the only single of the collection not either later released on or taken off of a long-playing album, having been recorded during the sessions for Highway 61 Revisited.
When this album was remastered for its 1997 issue on compact disc 30 years later, a slightly longer alternate mix of "Positively 4th Street" was substituted for the original single version. In 2003, this album was released along with Dylan's two other greatest hits compilations in one four-disc boxed set, as Greatest Hits Volumes I–III.
An audiophile version of the album was released in August 2012, mastered by Steve Hoffman for the Audio Fidelity label as a 24-kt gold-plated CD. This disc is a limited edition of 5,000 individually numbered copies. Like the 1997 remaster, this CD contains a longer version of "Positively 4th Street."
Read more about this topic: Bob Dylan's Greatest Hits
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