I've always enjoyed rewatching the 1964 film Robin and the 7 Hoods with Frank Sinatra, Dean Martin, Sammy Davis Jr, and Bing Crosby.
The film is influenced clearly by Damon Runyon's crime stories. I love the cinematic camaraderie of the Rat Pack entertainers as well as the humor and drama of this musical gangster film. I especially love the songs, which were scored by Nelson Riddle.
You can watch Frank Sinatra sing the classic My Kind of Town (Chicago is) in a clip from the film via the below link:
https://www.youtube.com/watch?v=don1x4DHn2A
You can also watch ole Dino sing Any Man Who Loves His Mother from the film via the below link:
https://www.youtube.com/watch?v=7NdcSnNSV-0
And you can listen to a selection of songs from the film via the below link:
https://www.youtube.com/watch?v=AJ_EJbjdMnk&list=PL3QK-FeOu2ccno7_XuoIuHKRE7jpsvWYa
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