9. Self Portrait - Bob Dylan
From the very start of his career, Bob Dylan was never one to go with the flow. Despite being born and bred in the folk scene in New York, Dylan's way with words quickly registered with the public, labelling him as the Voice of His Generation before he was even ready for it. Even though it seemed like Dylan could do no wrong, he did end up testing that theory on Self Portrait.
Stretching across a double album, this is easily the most divisive record in Bob Dylan's catalog. While most of the songs are a return to the folkier side of his musical personality, there are also some questionable choices that not even Dylan could have excused. Though covering someone like Paul Simon is something that might be cool for Bob Dylan to do, it feels like wasted potential when we could have gotten another amazing verse from the man himself.
However, things start to make a lot more sense when you realize that it's somewhat of a gag. In an attempt to shake off his musical god persona, the mission behind Self Portrait was to give a snapshot of Dylan's life, which was often pretty scattered at the time. Though the Voice of A Generation tag ended up sticking, this at least proved that some god-tier acts are at least fallible.