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The working title of this film was Sleep It Off. According to Hollywood Reporter news items and other contemporary sources, Marilyn Monroe was originally cast in the film but turned down the role and was suspended by Twentieth Century-Fox. According to a modern biography of writer-director-producer Nunnally Johnson, he wrote the part of "Curly Flagg" specifically for Monroe. December 1954 items in Hollywood Reporter's "Rambling Reporter" column indicated that the studio wanted Monroe to appear in the film with Jane Russell, her co-star in the studio's highly successful 1953 production Gentlemen Prefer Blondes. In January 1955, the studio cast Sheree North as Curly and Betty Grable as "Stormy Tornado." Grable, a longtime Fox star, made her final screen appearance in How to Be Very, Very Popular. The film also marked the motion picture debut of comedian Orson Bean, and North's first starring role.
According to a February 25, 1955 Hollywood Reporter news item, Archer MacDonald was originally cast as "Eddie Jones," but was forced to leave the production due to ill health. Three days of scenes between MacDonald and North had to be re-shot. Although a March 9, 1955 Hollywood Reporter news item announced that the title song from the 1954 Fox hit Three Coins in the Fountain would be sung by Grable and North in How to Be Very, Very Popular, it does not appear in the final film. One of the included songs, "Shake, Rattle and Roll," which was written in 1954 by Ken Darby and Lionel Newman, was one of the most popular rock and roll songs of the 1950s.
Hollywood Reporter news items include the following actors and dancers in the cast, although their appearance in the completed picture has not been confirmed: Gus Lax, Bob Melton, Virgil Johansen, Jesse Lucas, Willard Mack, Jean Acker, Gertrude Astor, Leah Baird, Gertrude Carr, Myna Cunard, Minta Durfee, Gertrude Mack, Eva Novak, Dorothy Phillips, Ida Pratt, Arline Pretty, Harry Denny, Paul Power, Reginald Simpson, Colin Ward, Dan Dowling, Tom Gibson, Harlan Hoagland, Colin Kenny, Buck Russell, Scott Seaton, Bernard Sell, William Raisch, Pat Cortland, Susan Brown, Beverly Jordan, Barbara Goodrich, Roy Clark-Lee, Charles Bondi, Ricky Riccardi and Edgar Johnson. Modern sources add Leslie Parrish (Girl on bus) to the cast.
According to biographies of Johnson, he took the subplot of "Curly" being hypnotized from the Lyford Moore and Harlan Thomspon play Sleep It Off. Edward Hope's novel and Howard Lindsay's play were earlier used as the basis for two films: She Loves Me Not, a 1934 Paramount production directed by Elliott Nugent and starring Bing Crosby, Miriam Hopkins and Kitty Carlisle (see AFI Catalog of Feature Films, 1931-40); and the 1942 Paramount picture True to the Army, directed by Albert Rogell and starring Judy Canova, Allan Jones and Ann Miller (see AFI Catalog of Feature Films, 1941-50). As noted in modern sources, the 1959 United Artists release Some Like It Hot, directed by Billy Wilder and starring Monroe, Tony Curtis and Jack Lemmon, bears a strong resemblance in plot to the Hope and Lindsay play and novel, which present the predicament of a witness to a murder who must mask her identity to hide from the killer. Another film employing a similar theme was the 1992 Touchstone Pictures comedy Sister Act, directed by Emile Ardolino and starring Whoopi Goldberg.