20 Times Artists Dared to Sing Sinatra’s Signature Hits

Cahn and Van Heusen wrote this for the 1964 Robin and the 7 Hoods, a Rat Pack film, and Sinatra’s recording became the definitive Chicago anthem. Taylor’s acoustic guitar version removed the Las Vegas spectacle entirely, leaving something that felt more like a quiet affection for a city than a showbiz declaration of loyalty. It is a gentle reading of a song that Sinatra invested with considerable bravado, and the contrast between Taylor’s warmth and Sinatra’s swagger reveals different but equally valid emotional possibilities in the lyric.