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Robin and the 7 Hoods began with Jack Warner, who wanted Frank Sinatra to make a musical akin to the good old days with new songs.
Sinatra agreed and brought members of the Rat Pack to assist with the gangster musical.
1. Peter Lawford was originally cast.
However, after a falling out with Sinatra, he was replaced by Bing Crosby. Crosby had previously worked with Sinatra in High Society and was excited to work on another musical – what would actually be his and Sinatra’s last. Crosby’s son was also hired for the film and played one of Sinatra’s men standing in the background of the pool scene.
2. Tragedy hit on the set.
Shortly after the assassination of JFK had changed the feeling on the set (read more about that here), Sinatra was hit again. On December 8, 1963, his nineteen year old son was kidnapped and held for ransom. The FBI apprehended those responsible and the money was returned. Frank Sinatra Jr. said, “I was scared. I was a little bit nervous naturally, but the only thing I could do was hope for the best.”
3. Gene Kelly was originally involved.
The film was originally part of a three movie package where Kelly would produce Robin, then co-star with Sinatra in another film, and finally direct one more. The pair had already worked together on Take Me Out to the Ball Game, Anchors Away, and On the Town. However, Sinatra’s rehearsal style different from Kelly. “I really loved [Frank] and that was the reason I was walking out because it was my intention to remain friendly with him,” Kelly recalled.
4. A song was cut.
“I Like to Lead When I Dance” was cut from the final picture. Originally, it appeared in the scene where Barbara Rush’s character woos Frank Sinatra in her home. However, Sinatra, who was also an executive producer, felt that the song slowed down the pace for the film and removed it. The instrumental can still be heard in the background when Dean Martin’s character is introduced for the first time.