Usually means: Western performer singing on horseback.
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We found 3 dictionaries that define the word singing cowboy:

General (3 matching dictionaries)
  1. the Singing Cowboy: Oxford Learner's Dictionaries
  2. singing cowboy: Wiktionary
  3. Singing cowboy, The Singing Cowboy (film): Wikipedia, the Free Encyclopedia

Definitions from Wiktionary (singing cowboy)

noun:  (music) A subgenre of country music and western music honoring the cowboy life and the West.
noun:  Used other than figuratively or idiomatically: see singing, cowboy.

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