Produced by Sinatra's production company Boots Enterprises, Inc. and sponsored by Royal Crown Cola, the show was originally broadcast on the NBC television network on December 11, 1967.

The TV special was unlike most musical programs of its time, with the numbers lip-synced outdoors on locations instead of the usual stage-bound production filmed before a live audience.

Sinatra states in the commentary track on the DVD release that the seemingly spontaneous kiss was carefully planned and deliberately timed for the end of filming, when Davis had to leave for another job and could not shoot a retake.

It features guest appearances by her father Frank Sinatra, Dean Martin (her "fairy goduncle" who performs a solo song and a duet with her), Lee Hazlewood (who wrote most of her hit songs), dancer David Winters (who was also nominated for a special Emmy for his choreography) and Sammy Davis Jr. RC Cola sponsored the show and created five lavish commercials.

It features a commentary track by director Jack Haley Jr. and Sinatra, who reflects on her wardrobe and regrets not including her signature song, "These Boots Are Made for Walkin'", as part of the production.