"The Way" by Fastball was inspired by the story of an elderly couple from Texas who drove to a nearby family reunion and kept going. Fastball's bass player imagined them taking off and having fun like they were young. The story didn't end well: the couple was later found dead after they crashed in a canyon.
"Sloop John B" is a traditional West Indian folk song, and it was a huge hit for The Beach Boys in 1966. They tweaked the lyric, "This is the worst trip since I've been born" to "...I've ever been on" as a wink to acid culture.
Bob Dylan's most popular song is "Like A Rolling Stone," which tells the story of a wealthy woman whose money and friends fall away. Dylan offers these mockingly encouraging words: "When you ain't got nothing, you got nothing to lose."