Son of Paleface
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Son of Paleface (1952), a western comedy film and a sequel to The Paleface (1948), remains widely regarded as superior to the earlier movie.
Son of Paleface features Bob Hope, who plays the son of the central character in the earlier film, Jane Russell (also back from the first film, albeit as a different character), and Roy Rogers, who sings his song "A Four Legged Friend" to his horse Trigger.