Rio Bravo (1959)
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No. Dean Martin and Ricky Nelson were two of the most popular singing stars in their field at this time and despite the fact that there is one small sequence where the two of them sing a couple of songs, it's not a Musical. Although probably not properly called singing, Walter Brennan had some songs that were on the charts and he had some albums. He joined Dean and Ricky in singing "Cindy, Cindy." Edit (Coming Soon)
In 1966, John Wayne and the director Howard Hawks reunited for El Dorado. In El Dorado it's Robert Mitchum playing the drunk sheriff and Wayne isn't a lawman but a gunslinger trying to help Mitchum get back on his feet. James Caan plays a character called Mississippi more or less replacing the Colorado character here and Arthur Hunnicutt plays the ageing deputy Bull - replacing the Stumpy character. The film doesn't begin to resemble Rio Bravo until around the middle act but both have enough similar main characters and plot scenarios to the point that it's regarded as a re-working.
In 1970, Hawks and Wayne once again joined up for a western called Rio Lobo which again many regard as a re-working of Rio Bravo but it's actually very different. The first act is set during the Civil War and when the film becomes more of a traditional western it actually uses plot elements from both Rio Bravo and El Dorado.
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No. Dude is an ex-deputy sheriff in the opening scene. He helps Chance capture Joe Burdette and take him over to jail and Chance gives him his old job back. This isn't shown and the opening few minutes are dialogue free but it's clear that he isn't a lawman at the start of the film by the fact that Dude is unshaven and dirty looking and isn't wearing a badge. Then later on, Chance remembers to give Dude his guns back that he's been storing for him and while they go over to retrieve Dude's clothes from the hotel, he asks Chance what his pay will be. Edit (Coming Soon)