11. "It's All Over Now, Baby Blue" (1965)
In the film Don't Look Back, Dylan sits around his room in London's posh Savoy Hotel, surrounded by hangers-on. Bored, he picks up an acoustic guitar and plays a new song he's just written: "It's All Over Now, Baby Blue." He has an evil grin on his face; after the first two verses, it's the only smile in the room – everyone else looks shattered. The party's definitely over.
The song is his devastating farewell to innocence, kicking Baby Blue out into the street, whether that means the end of a friendship or his abandonment of the folk scene. After he was famously booed offstage for going electric at the Newport Folk Festival, and returned with an acoustic guitar, this is the song he chose to play as his hard-ass response.
It instantly became one of his most covered songs. But nobody's ever sung "Strike another match, go start anew" with the menace of Dylan himself.