"It Happened in Monterey" was written for the 1930 musical film King of Jazz.[2] The film featured Paul Whiteman and his orchestra,[3] while the song, written in waltz time, was composed by Mabel Wayne, with lyrics by Billy Rose.[4][5] Though the lyrics refer to the city of Monterrey in "Old Mexico",[6] the song title was misspelled, leading to popular references to the city of Monterey, California.[7] The song was performed by John Boles and Jeanette Loff in the film.[8] The song appears in a sequence of disparate musical performances, each introduced by a caption card, that appear between the two main production numbers.[9]
The Paul Whiteman Orchestra then recorded the song for Columbia Records on March 21, 1930, featuring vocals by Jack Fulton.[10] This recording features significant solos for flute and piccolo performed by Bernie Daly.[11] The recording was a hit. Researcher Joel Whitburn estimates that this record would have charted at number 2 in April 1930.[12]
By the 1950s, the song had declined in popularity and was rarely sung until it was revived and popularized again by Frank Sinatra.[17] Sinatra recorded it for his 1956 Capitol release Songs for Swingin' Lovers!, to an arrangement and orchestration by Nelson Riddle. Biographer John Frayn Turner writes: "'It Happened in Monterey'... had never sounded like that before or since".[18] Biographer Spencer Leigh notes the "looseness of his phrasing in the second chorus".[17] Sinatra began performing it live. It features as the second track on his 1957 live album Sinatra '57 in Concert,[19] and also appeared on the original UK pressing of Come Fly with Me as a replacement track for the banned "On the Road to Mandalay".