That old footage was from early in his career, prior to his growth and before he had something called creative control. When Chappelle expressed the reasons why he left the show, including, pushing back against execs wanting him to wear a dress, among a number of other things, that Chappelle disagreed with in expressing his art. Those "Why did you leave the show" interviews had nothing to do with some of the old roles he played, to address specifically.
The "never wore a dress" or "never played a female role" was not something Dave ever said in the first place. I don't find what Dave did not say to be confusing at all.
In general, folks get things wrong, like some of the commentors in that same tweet, incorrectly stating that Dave lied about not getting royalties. Just making up shit with ASSumptions.