Song of the Day #1,166: ‘What a Funny Girl You Used to Be’ – Frank Sinatra

After opening with the gentle ‘Elizabeth,’ Part Two of Frank Sinatra’s Watertown moves on to the album’s most playful song. Again we are given a glimpse at the woman who is the cause of all this heartbreak, and this time it’s a very sympathetic portrait.

Of course none of the songs on Watertown are particularly upbeat and even this one, despite its amusing lyrics (“you’d fall for lines so easily… whatever they were selling, you’d buy three”) is tinged with sadness and regret.

The way Sinatra sings the single line that makes up the chorus — “What a funny girl you used to be” — captures the loneliness of a man whose happiest memories are a constant source of suffering.

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