Saturday Night (Is the Loneliest Night of the Week)

A wartime lament written from the perspective of a musician who’d rather be with his sweetheart than playing another Saturday night gig. Sinatra’s 1944 recording was a #1 hit, one of his biggest during his Columbia Records years, and the song became a staple of his early live performances.

The irony of a song about loneliness becoming one of the most popular recordings of the year was not lost on Cahn — it simply confirmed his belief that the most personal emotions are also the most universal.