Frank Sinatra appeared in the 1955 film version of the Frank Loesser musical Guys and Dolls. But he was miscast in the virtually nonsinging role of Nathan Detroit, while Marlon Brando took the part of Sky Masterson, who gets to sing such songs as "I've Never Been in Love Before" and "Luck Be a Lady." What singing Sinatra did do never appeared on a legitimate album because he was contracted to Capitol Records and the soundtrack music was controlled by Decca, which only issued a four-track EP of songs sung by Brando and Jean Simmons. Sinatra attempted to make up for all this almost a decade later when he chose Guys and Dolls as one of four musicals to record using performers from his Reprise Records label under the rubric Reprise Musical Repertory Theatre. He and his Rat Pack cronies Dean Martin and Sammy Davis, Jr. were well-suited to this show full of songs sung by (and in the vernacular of) small-time gamblers; it was a persona not all that far removed from the small-time gangster identities they often adopted.
For the most part, Sinatra did not bother to maintain strict character casting, making the album more of a various-artists collection than a real studio cast album. For example, "I'll Know" and "If I Were a Bell," both sung in the show by the character of Sarah Brown, were handled separately by Jo Stafford and Dinah Shore. Sinatra joined Martin and Bing Crosby on "Fugue for Tinhorns" and "The Oldest Established (Permanent Floating Crap Game in New York)," and teamed with Martin on "Guys and Dolls," songs mostly handled by minor characters in the show, but he also gave himself "I've Never Been in Love Before" and "Luck Be a Lady." ("My Time of Day," another of Sky Masterson's numbers, was cut.) Using arrangers such as Billy May and Nelson Riddle, the cast made an album that sounded for the most part like 1950s pop singer music. The great exception came with the three songs -- "Take Back Your Mink," "Adelaide's Lament," and "Sue Me" -- handled by Debbie Reynolds, who seemed to have come to the studio deeply in character as Adelaide, the nightclub singer and longtime fiancée of Nathan Detroit. Adelaide's songs are broadly comic, but especially in the context of the other straightforward treatments, Reynolds' interpretations sounded wildly overdone. Nevertheless, the album remained enjoyable for the work of Sinatra, Martin, Crosby, and Davis (who sang the revival-styled "Sit Down You're Rockin' the Boat"). [Note that the 1969 reissue of the album on Harmony Records is abridged.]