"Watertown is Frank Sinatra's most ambitious concept album, as well as his most difficult record. Not only does it tell a full-fledged story, it is his most explicit attempt at rock-oriented pop ... Weaving together prominent electric guitars, keyboards, drum kits, and light strings, Calello uses pop/rock instrumentation and production techniques, but that doesn't prevent Sinatra from warming to the material. In fact, he turns in a wonderful performance, drawing out every emotion from the lyrics, giving the album's character depth".