The mid-60s was a time of musical, cultural, and political change and no album reflected the spirit of the era more than Bob Dylan’s second Album, “The Freewheelin’ Bob Dylan”. Released in 1963, the album was a shock to the music industry, an unexpected masterpiece of completely original songs from a prolific songwriter full of new ideas and talent. Soon after its release, top stars began to cover its songs. Most memorable of the time was Peter, Paul, & Mary’s number 2 hit, “Blowin’ In the Wind”. Other songs that would make both a cultural and musical impact were “A Hard Rain's A-Gonna Fall”, “Don’t Think Twice, It’s All Right”, and “Masters of War”.
Besides the changes he augmented in the musical world, the young Bob Dylan was experiencing changes in his personal life as well. In 1965, he began a long-term relationship with folk singer Joan Baez.
Moving away from the acoustic to the electric, Dylan gave his folk song, “Mr. Tambourine Man” to the Byrds to record as an electric arrangement. Nearly instantly, the song became a huge hit.
The following 2 videos... Bob Dylan's original "Mr Tambourine Man" and the Byrds version highlights the differences in tempo.
But... Dylan didn’t fare as well when he tried to switch to electric. At the 1965 Newport Folk Festival, he was booed off the stage during his appearance with the Paul Butterfield Blues band.
 
 
Mid-year, Dylan recorded the album Highway 61 Revisited, which included the hit single “Like a Rolling Stone”. At six minutes, the song was the longest recorded to date.
His relationship with Baez ended and he began dating model Sara Lowndes who he married in the latter part of the year. He also hired a new touring band, the Hawks, who would later gain fame after they changed their name to “The Band”.
Fate saw Dylan speeding down many new roads and in a simple twist, brought the road up to meet him. On July 29, 1966, a near-fatal motorcycle accident brought his career to a screeching halt. The young, but now established star retreated to his home in Woodstock to recuperate. The Hawks joined Dylan at the rented house “Big Pink” where they recorded country-style music that was not meant for release. Eight years later the tapes found their way to the public as “The Basement Tapes”.
Bob Dylan - “Once in a while, the odd song will come to me like a bulldog at the garden gate and demand to be written. But most of them are rejected out of my mind right away. You get caught up in wondering if anyone really needs to hear it. Maybe a person gets to the point where they have written enough songs. Let someone else write them."