The Beatles - "Octopus's Garden" (1969)
This track might be the most unexpected on this list but not because of its title. This is one of the few Beatles tracks that was not written by John Lennon or Paul McCartney. Instead, Ringo Starr churned out this odd tune with an impossibly hummable melody. But the song has an underlying origin that is a bit sad.
Starr got the idea for the track after ordering some fish on a boat but got squid instead. He ate it and thought it was OK. This led to a discussion with the boat's captain and the captain told Starr of how octopi collect rocks and other seabed items for gardens.
At the time, however, the Beatles were falling apart because there was stress between the members. Starr wrote the tune because he wanted to escape the drama and be under the proverbial sea as well. This song was a form of escapism for him and it became one for listeners as well.
The Rolling Stones - "Paint It Black" (1966)
There is no escape from the meaning of this track, either. It is all there in the title. Instead of some happiness with painting over what might currently be happening, the song is one about a person who literally cannot find any hope. Their mate has passed and they do not know what to do with themselves.
To be so bleak in the mid-1960s was rare. We were still mostly wanting snappy tunes with a bit of wry humor or heartbreak. For the Rolling Stones to give us something that is frantic bleakness was something we did not know we needed, but turned out to be something people wanted. In the UK, the song spent two weeks at number one.
One of the more unusual aspects of the song is Bill Wyman's fretless bass. This gives the track more of a thumpy sound that seemingly makes it more eerie. In others words, pure perfection.