Sing, You Sinners (1938) was created because director Wesley Ruggles had worked with Bing Crosby in College Humor (1933) and Mississippi (1935) and wanted to direct him again. The problem was, he needed the right vehicle. Ruggles and writer Claude Binyon were neighbors of Crosby's in Toluca Lake, and got to know the real Bing. Binyon told Ruggles that he wanted to write a film in which Crosby's character was true to life. Having seen Bing at home and at the racetrack (where Crosby owned a large stable of horses), he came up with a story about a lazy singer who doesn't want to sing, and gambles away his money on horses. Rounding out the cast were Paramount's up-and-coming leading man, Fred MacMurray, playing Bing's older brother Dave (despite being five years younger than Crosby), and 12-year-old Donald O'Connor as Crosby's kid brother, Mike. Also appearing in the film were Elizabeth Patterson as Crosby's mother, and Ellen Drew, then known under the name of Terry Ray, as Martha, Dave's girlfriend.

The original title of the film was The Unholy Beebes , which Crosby liked, but the studio didn't; they thought the audience wouldn't be able to pronounce Beebe, and changed it to Harmony for Three before settling on Sing You Sinners . The casting changed as well. Fox star Don Ameche and MGM's Mickey Rooney were booked to play Crosby's brothers before Ameche dropped out. Rooney was attached to the project up until just before shooting started in April 1938, but MGM suddenly took him off the picture, leaving the producers without a kid brother for Bing. It was Paramount executive Artie Jacobson who was tasked with coming up with a replacement, fast. He found O'Connor performing at a benefit for the Motion Picture Relief Fund (now the Motion Picture and TV Fund) and signed him. For MacMurray's girlfriend, Jacobson suggested Terry Ray, who had appeared in a bit part in Crosby's Rhythm on the Range (1936). Jacobson wanted to take Ray to meet Crosby to see if she met with his approval, but Bing, who was known for his casual attitude on set, was unconcerned, telling Jacobson that if Ruggles was okay with her, then he was, too. For fun, Jacobson asked Crosby to be the one to let Ray know that she had the job because he wanted Bing to see how excited she would be. When Ray was brought to the set and told the news, she fainted dead away. Before the film was released, Terry Ray had her name changed to Ellen Drew, which was the last of several names that the studio tried out. Crosby said that he got so confused by this that he called her Ellen Terry, after the famous 1800s stage actress.

Crosby had been cast as the romantic leading man in all of his pictures to date, and was apparently tired of it, saying in an official Paramount press release that he was happy that Fred MacMurray got the girl instead of him. He claimed that he'd made enough love scenes over the past few years "And I haven't got one in Sing, You Sinners . Whoopee! What a break!" Crosby caught a break with the music for the film - he sung two songs that would become classics: Small Fry , written by Hoagy Carmichael and Frank Loesser, and I've Got a Pocketful of Dreams , by James Burke and James V. Monaco.

Sing, You Sinners was a happy time for Crosby, as the film was shot on location at the Pomona Fairgrounds and Santa Anita racetrack in Arcadia, north east of Los Angeles. Crosby celebrated his 35th birthday during production on May 2nd, although the studio clung to the fiction that he was 34.

When Sing, You Sinners opened at the Paramount Theater in New York City on August 17, 1938, it was well received by the critics. Life magazine wrote that Joe Beebe was a good role for Bing because he "abandons the romantic roles that his stocky figure makes him unsuited and takes a comfortable, happy-go-lucky part that fits him like a glove." The Prescott Evening Courier praised "outstanding performances turned in by two of the screen's newest star discoveries, Ellen Drew and Donald O'Connor. [...] Miss Drew exhibits a freshness and sincerity which should certainly carry her to the top of the ladder in Hollywood. O'Connor, who plays Bing's younger brother and jockey, coming to the screen after years on the vaudeville stage, can act, sing, play an accordion, and ride a racehorse with equal ability." O'Connor's performance in Sing, You Sinners led to a contract with Paramount and a film career that lasted sixty years.

By Lorraine LoBianco

SOURCES:

"Bing Crosby Portrays Serious Role in 'Sing, You Sinners'" Spokane Daily Chronicle 7 Oct 38
Giddins, Gary Bing Crosby: A Pocketful of Dreams: The Early Years 1903-1940
The Internet Movie Database
Reed, John Howard More Movie Musicals
Paris, James Robert ad Pitts, Michael R. Hollywood Songsters: Garland to O'Connor
"Sing, You Sinners: Bing Crosby Croons and Fights" Life 5 Sept 38