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The working titles of this film were Intermission, The Red Nichols Story and Red Nichols. The Hollywood Reporter erroneously listed the film's running time as 157 minutes. The Five Pennies is based on the life of noted jazz musician Ernest Loring "Red" Nichols (1905-1965), who, after being taught to play the cornet by his father, began playing professionally at a young age. Influenced strongly by the "Dixieland" style of jazz, Nichols played in various bands before beginning to record and appear on his own in the mid-1920s. With a rotating roster of bandmates, Nichols usually billed his group as "Red Nichols and His Five Pennies," and quickly became established as one of the leading players of "hot" jazz. As depicted in the film, many music legends such as Jimmy Dorsey, Benny Goodman, Glenn Miller and Gene Krupa performed in Nichols' band early in their careers.
Nichols' wife, Willa Stutsman, was a dancer, not a singer as portrayed in the film. When their young daughter was afflicted by polio in 1942, Nichols quit playing and worked in the San Francisco shipyards during World War II. After the war ended, Nichols returned to music and increasing fame, and in 1956, was featured on the This Is Your Life television show. Nichols is widely considered to be one of the most influential jazz musicians of the 1920s. As noted in the onscreen credits, Nichols himself played the cornet and trumpet solos that are heard in the film. Actor Danny Kaye spent several months learning to play the cornet in order to be able to duplicate Nichols' fingering.
According to information in the Paramount Collection at the AMPAS Library, Kaye became interested in playing Nichols in late 1954, when he signed an agreement with Paramount to have his company, Dena, and Paramount co-produce the property. In November 1954, Variety noted that Nichols had "turned over 2,500 [of his] musical arrangements and scores" to Paramount's music department. The Beverly Hills Citizen review of the picture noted that Don Hartman, the head of production at Paramount from 1950 to 1956, was the first producer who became interested in developing the project. 1954 and 1955 Hollywood Reporter news items list first Paul Jones and then Pat Duggan as the producer. In July 1955, Hollywood Reporter listed Robert Parrish as the film's potential director. Los Angeles Times reported in July 1956 that Melville Shavelson and Jack Rose were taking over the project from Melvin Frank and Norman Panama, who also served as a producing-writing-directing team for Paramount.
According to studio records and contemporary news items, Daniel Fuchs, David Shaw, Edward O. Berkman, Raphael D. Blau and John Michael Hayes worked on the film's screenplay; however, the extent of their contribution to the completed film, if any, has not been determined. An August 1955 studio memo reveals that Ray June was originally set as the picture's director of photography, but due to "serious script trouble," the project was delayed. In January 1957, pre-production on the film was stopped altogether, with a studio memo stating that the picture would not be produced until 1958.
Although pre-production work on the film did begin again in early 1958, principal photography was delayed until October 1958 due to the musicians' union strike, which precluded the participation of musicians such as Louis Armstrong. A May 1958 Hollywood Reporter news item reported that Paramount offered to release Kaye from his contract to make the film with them so that he could make it for release by United Artists. As an independent studio, UA would have been more likely to sign an "interim agreement" with the musicians' union, and if so, then the film could have been made without Armstrong and the other musicians breaking the strike. A distribution deal with UA could not be reached, however, and the project was continued at Paramount.
A February 19, 1958 Hollywood Reporter news item announced that Nick Castle was set to act as the picture's choreographer, but the delay in production May have caused Castle to drop out and be replaced by Earl Barton. According to other February 1958 Hollywood Reporter news items, Polly Bergen was considered for the role of "Bobbie Meredith" and singer Bob Anthony was tested for a part. An April 1958 item in Hollywood Reporter's "Rambling Reporter" column noted that Patti Page was also under consideration for the role of Bobbie. A September 1958 Hollywood Reporter news item stated that Benny Goodman was in negotiations to play himself, but an October 1958 "Rambling Reporter" item asserted that the deal fell through because of Goodman's high salary demands. According to studio records, young actresses tested for the part of "Dorothy" as a teenager included Patty McCormack, Beverly Washburn, Sandy Descher, Karen Green and Andrea Lee.
Although Hollywood Reporter news items stated that June White and Paul Sullivan had been cast in the film, their appearance in the released picture has not been confirmed. A November 28, 1958 Hollywood Reporter news item reported that Kaye cast his daughter Dena, for whom his production company was named, as a hospital ward patient. According to the news item, the cameo was to mark her motion picture debut, but her appearance in the completed film also has not been confirmed. Nichols appears briefly in the picture as one of the "Clicquot Club Eskimos," in the sequence in which Kaye, as "Nichols," appears on a number of radio shows, singing "(Back Home Again in) Indiana" in various styles. Studio records note that second unit shooting was done on location in San Francisco and New York. Other California locations included Terminal Island, Long Beach, the Rancho Los Amigos Hospital in Downey, Sherman Oaks and the Brown Derby restaurant in Hollywood.
According to a March 1959 Hollywood Reporter news item, Kaye's ex-business manager, Edward Dukoff, sued Kaye, his wife, Sylvia Fine, and Dena Pictures, Inc., claiming that he was entitled to a percentage of the profits from any of Kaye's films developed between 1948 and 1955, including The Five Pennies, on which Dukoff allegedly worked in 1953 and 1954. The disposition of the suit has not been determined.
The film received Oscar nominations for Best Cinematography (Color), Best Costume Design (Color), Best Original Song for "The Five Pennies" and Best Music, Scoring of a Musical Picture. In addition to a Golden Globe nomination for Best Motion Picture-Musical, the picture received a Grammy nomination for Best Soundtrack Album, Original Cast-Motion Picture or Television. The Five Pennies marked the final film appearance of silent movie actress Blanche Sweet (1895-1986), who had not appeared in a picture since the 1930 RKO production The Silver Horde (see AFI Catalog of Feature Films, 1921-30). Musician Shelly Manne again portrayed fellow drummer Dave Tough in the 1960 Columbia release The Gene Krupa Story (see below).