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More than 35 movies.
When I did a search at IMDB for "Feature Films" that were "Westerns" and had "John Wayne" listed in the credits; I got 91 films. Some of these were only produced by Wayne, for some he had only a bit part, and some could be argued as not being westerns. So let's say "about" 80.
John Wayne Died June 11, 1979 in California at the UCLA Medical Center.
Yes, John Wayne dressed as a woman for a comedic scene in the 1972 film "The Cowboys." In the movie, he played the role of a rancher who disguises himself to avoid detection. While this was a humorous moment, it was not a common occurrence in his career, as Wayne was primarily known for his tough-guy roles in Westerns and action films.