While I have said Dylan's self-titled first album is my favourite of all of his albums, in my opinion, his second album,
The Freewheelin' Bob Dylan, is the best of all of his albums. One of the reasons for the quality of this album over the first album might be that the first album was churned out very quickly (having been recorded in a mere two days). Dylan was given a much longer time to record
Freewheelin' with recording commencing on April 24, 1962 and Dylan recording off and on until the eighth and last recording session of the album taking place exactly one year later on April 24, 1963. Perhaps this is why
Freewheelin' probably has more outtakes than just about any other album that Dylan recorded. Speaking of the outtakes, I really cannot recommend them enough. A strong argument could be made for the
Freewheelin Outtakes being the absolutely best bootleg that Dylan has not officially released yet.
If I was going to recommend one specific outtake that you should listen to, I would recommend Dylan's redition of Big Joe William's "
Baby, Please Don't Go" which was recorded on April 25, 1962, the second day of recording for the album. As I said in a
different thread, the
Freewheelin Outtakes version is not only Dylan’s best cover of this song but maybe the best song he did in ‘61/62 that is not on an officially released album. There is a crispness to his guitar and harmonica playing on this version of the song which demonstrates that in this time period, Dylan could really play. He also has a great blues-y vocal. This song showcases Dylan
as the folk music performer rather than the songwriter he later became known for. All of that being said, "
Baby, Please Don't Go" is just the tip of the iceberg. Highest possible recommendation for these outtakes!
The other thing I find interesting about this time period is that is appears that it was during the recording of this album that a power struggle developed between producer, John Hammond, and Dylan's manager, Albert Grossman. The result was that mid-way through, Hammond was replaced with
Tom Wilson who went on to record the next three Dylan's albums until he was replaced by Bob Johnston early on during the recording of
Highway 61 Revisited.