After Closing Time, Waits’ sound shifted gears from the emulated folk sound into a colder and paradoxically both rougher and smoother, jazz sound that is more familiar to Waits’ fans.
It was no coincidence that the next record, The Heart of Saturday Night, had album art styled after Sinatra’s concept album In the Wee Small Hours of the Morning. Waits’ biggest inspiration at the time had to have been Sinatra, as the record takes a more subtle approach. Waits’ voice is still much like it was in Closing Time, although he seems a bit more comfortable. While Closing Time had only a couple of piano ballads, The Heart of Saturday Night is a piano ballad album from start to finish, painting a somber picture. The combination of Sinatra and Dylan inspiration is odd, but it’s nice and slick.