This compilation album was released in 1964 by Reprise Records, gathering songs previously recorded by Frank Sinatra between 1962 and 1964. The title references two of the most popular tracks on the record: 'Days of Wine and Roses' and 'Moon River', both Academy Award winners for Best Original Song.
Production was handled by Sonny Burke, a frequent collaborator of Sinatra at Reprise. The album features orchestral arrangements conducted by Nelson Riddle and other arrangers, showcasing Sinatra's mature vocal style in the 1960s.
Although not one of his most commercially successful albums, it reflects Sinatra's ability to interpret ballads and pop standards of the era. The cover features a photograph of the singer against a dark background, typical of Reprise's design in those years.