Just came across this gem.

Ronald Reagan in a drag show ~~cross dressing~~ in "This Is the Army". Quite an army, rawr.

https://en.wikipedia.org/wiki/This_Is_the_Army

Edit: It may be this photo is someone else, Reagan just does the opening show call. Anyway, Reagan is in the show, even if this isn't him.

https://www.youtube.com/watch?v=ZbBZRnWoPbY