He does have a point. Look at the latest movies in the theaters or soon to be:  Big Momma's House 2 w/Martin Lawrence dressed as a woman and Madea's Family Reunion w/Tyler Perry dressed as a woman.

I think Br. Dave is starting to trip. Hollywood (and live theatre) has a long tradition of having men appear in drag. Does anyone remember Jack Lemmon  and Tony Curtis in Billy Wilder's movie Some Like It Hot? At various times in their careers Jack Benny, Bob Hope and Milton Berle appeared in drag. In 1995, Wesley Snipes and Patrick Swayze appeared in drag in a movie with the long and weird title To Wong Foo, Thanks for Everything, Julie Newmar.

Dave Chappelle may not enjoy dressing in drag (I can't blame him) but I think that the late Flip Wilson enjoyed every minute he was in panty hose.  I suspect the same is true for Tyler Perry.  I know nothing at all nor would I hazard a guess about either man's sexual preferences or tastes.

I think what motivates Hollywood to have men dress in drag is that it makes for good box office.  I'm not at all interested in movies, television shows or plays featuring Martin Lawrence or Tyler Perry but there are hundreds of thousands of people who are.  And as long as they are interested Lawrence and Perry and their collaborators will keep giving them what they want.

Haw.

I think Chapelle was just funnin'. In addition to all the examples ptc gave, add every single British comic ever born. It sounds like he spotted a recent flurry of examples and made a nice little riff on it.

Where would Jamie Fox be without Wanda?

British comics don't count. Nothing British counts...from Monty Python to Neil Gaiman, it's obvious they're the more mature branch of Anglo-Saxon culture.

Hold on. I gotta rewind and see how we jumped from "men in dresses" to "more mature."

Haw.

Just seeing if you're paying attention out there...

Thing is, I'm pretty sure I heard the same complaint years ago. Can't remember who or where.