Favorite song from Side 1: "Don't Think Twice, It's All Right"
Originally released on Dylan's iconic 1963 album, The Freewheelin' Bob Dylan, "Don't Think Twice, It's All Right" is a folk classic -- a shining example of Dylan's early acoustic songs. Just an acoustic guitar, a harmonica, and a mediocre singer spewing finer poetry than you could ever hope to write.
Favorite song from Side 2: "My Back Pages"
Since the first time I ever heard this song -- which originally came out on his 1964 album Another Side of Bob Dylan -- I vowed to live my life by the chorus: "But I was so much older then / I'm younger than that now." It's working.
Favorite song from Side 3: "The Mighty Quinn (Quinn The Eskimo)"
Side 3 features a few songs that were made into more famous covers than the originals, specifically "All Along the Watchtower" and this one. While I prefer Manfred Mann's cover version to the original, "The Mighty Quinn (Quinn The Eskimo)" is a fun song about an Eskimo named Quinn, to whom all the pigeons will run upon his arrival. And Dylan is backed by The Band on this track, so that's nice.
Favorite song from Side 4: "It's All Over Now, Baby Blue"
This song was part of Dylan's last true folk album, 1965's Bringing It All Back Home. He then went electric, for the good of music history, but one of his last great acoustic songs was "It's All Over Now, Baby Blue," a scathing diss track aimed at the worst shade of one of the three primary colors.
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