The 25 Greatest Songs of Paul McCartney’s Illustrious Career

15. “Eleanor Rigby” (1966)

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McCartney and the Beatles were in experimentation mode at this point in their careers. Strings and conceptional lyrics, the song was noticeably different from the group’s early pop favorites. The Revolver hit left some music fans wondering just who are these people that Paul and band are telling us about. It’s only 2 minutes, 8 seconds long.

14. “Penny Lane” (1967)

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McCartney wrote this song about his upbringing in Liverpool, thus touching on some personal nostalgia. The single hit No. 1 in the United States and was included on the U.S. version of Magical Mystery Tour. The song features a trumpet, flute and hand bell, all demonstrating how innovative the band was becoming.