- Frank Sinatra: “One for My Baby (and One More for the Road)” (Only the Lonely, Capitol, 1958)
If jazz and alcohol aren’t easy to separate, Frank Sinatra and alcohol are impossible to separate. That’s certainly true of the Capitol Years, the 1950s run of music that coincided with the creation of the Rat Pack and marked Sinatra’s transition from teenage sensation to musical and cultural icon. It also marked the tumultuous period of his marriage and divorce with Ava Gardner, the latter still fairly fresh when he recorded “One for My Baby.” The singer, drowning in his own melancholy as well as his liquor, hints at a doomed love affair (“We’re drinking, my friend,/To the end of a brief episode”), but the song is really about the self-pity of the barfly who sings it as he closes the place down. In Sinatra’s brilliant reading, that drunken despondency becomes somehow profound.
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