6. "Paint It, Black" (1966)
"We cut it as a comedy track," Richards confessed. Some comedy. "Paint It, Black" became one of the most flat-out frightening singles to ever hit Number One, driven by a droning sitar riff from Jones. Jagger sings about death, grief and sex ("I see the girls walk by dressed in their summer clothes/I have to turn my head until my darkness goes") over the band's repetitive stomp. The song was originally a conventional pop tune and, according to producer Andrew Loog Oldham, not a very promising one. Wyman's roiling bass line, written on a Hammond organ, pushed the Stones in a new direction. The sound was psychedelic yet disturbing. "It was a different style to everything I'd done before," Richards said. "Maybe it was the Jew in me. It's more to me like 'Hava Nagila' or some Gypsy lick. Maybe I picked it up from my granddad." The record company added a stray comma to the title, yet somehow the punctuation glitch made the song seem even more mysterious: "Paint It, Black."