the cover art is designed to set the mood for the music. the cover shows sinatra on an eerie and deserted street awash in blue-tinged street lights, reflecting the album's themes of introspection, lost love, failed relationships, depression, and night life. it is significant that sinatra is depicted alone, as loneliness during the "wee small hours" is a theme of the album. rather than at a rakish angle, sinatra's snap-brim hat is pushed back, suggesting resignation and openness. the artwork is reminiscent of film noir or a hardboiled fiction cover.