Watertown

Watertown tells the story of a nameless man in Watertown, New York, whose wife leaves him and their two sons for the city. Bob Gaudio of the Four Seasons produced it and co-wrote it with the lyricist Jake Holmes. After low sales in 1969, Sinatra agreed to the project. It is the only album on which he sang over pre-recorded orchestral tracks. The orchestra was recorded in New York at Columbia's 30th Street Studio in July and October, and Sinatra added his vocals at United Western Recorders in Hollywood in August and October. He did not record with the orchestra, though he attended the orchestral sessions, and he never again recorded his vocals without a live orchestra.

I Would Be in Love (Anyway) reached number four on the US Adult Contemporary chart. The album itself was Sinatra's only major release not to reach the Billboard top 100, and many people now count it among his finest. In a 2022 Sunday Review, Pitchfork's Sam Sodomsky called it an unsparing and bleak concept album and a fascinating outlier. He wrote that Gaudio and Holmes aimed to strip away everything that had come to define Sinatra's music, and he called the songs the sparsest and saddest Sinatra ever sang.

Gaudio and Holmes wrote all of the songs. Gaudio and Frankie Valli of the Four Seasons brought Sinatra a fully written album, and the story runs in two parts with an epilogue. Holmes told Ed O'Brien for the liner notes that he had Lazy Afternoon in mind as a model for the title song, because he wanted a languid feeling. The 1994 CD adds the epilogue Lady Day, which tells of the wife leaving for the city. The orchestra was conducted by Joe Scott on some tracks and Charles Calello on others, and Bill Miller and Al Viola backed Sinatra at the vocal overdubbing for Goodbye (She Quietly Says).