My dislike for Black men in drag really started with Martin Lawrence's role as Big Mama. To me, it was a cheap rip-off from Eddie Murphy's successful depiction of an entire family in the Nutty Professor series which included the mother and grandmother roles. In my opinion, Eddie was brilliant in those roles.
From what I recall, Geraldine was sassy with a lot of attitude and also flirtatious. Looking back on those episodes, Geraldine was always paired with big name stars like Bill Cosby, Muhammad Ali, and Tim Conway to name a few. Even though Geraldine was the comic relief in those skits it was his/her interactions with the stars that made the skits funny.
Next, I recall Martin Lawrence as "Sheneneh" on his own sitcom. Again, his interpretation was one of a woman with major attitude and sass who demanded attention. In this case, Sheneneh was the star and the role really relied on her outrageous behavior.
There was Arsenio Hall in Coming to America who portrayed a depraved, sex addicted woman who was willing to sleep with multiple men at the same time. I think it was funny because it came about totally unexpected, and the thought of him sleeping with himself is just hilarious.
On The Jamie Foxx show, Jamie played a woman named Wanda who was extremely ugly with strong sexual desires and attitude. I don't believe this portrayal worked because it had been done, with mixed reviews by Martin Lawrence.
There was Wesley Snipes actually playing a woman in drag in Too Wong Foo, Thanks For Everything, and Miguel Nunez as a basketball playing woman in Juwanna man.
Eddie Murphy portrayed multiple roles in Coming to America, none of them women, but I believe it was because of the success of his roles in that movie that he expanded to female roles in the Nutty Professor franchise, which by the way, were near genius.
So, why is the portrayal of Black women by Black men so successful and interesting? Well, in my opinion it's because of the importance Black women play in the life of their children. There is no stronger person in my life than my mother. My mother has been everything to me, strong, supportive, sensitive to my feelings, caring, giving, a disciplinarian, loving and the list goes on. I believe most men can relate to this but more so by Black men. More Black men are raised in single-parent households, led by their mother's, than any other race. Because of this, Black women often times play dual roles in the upbringing of their son's, having to be both the mother and the father. Obviously, a mom can't adequately fill the role of a man as a father to his son, and because of this inability to do so, mothers often exaggerate the guidance they give their son's. In a lot of cases, the mother will put their young son's in the role of the missing father, putting adult responsibilities on the shoulders of a child. I digress.
Anyways, most Black men can easily tell you about the strong women in their lives and the memories from their childhood of their mother's, grandmother's, aunts and cousins. I always compare my mother to E.F. Hutton, because when she talks, EVERYBODY LISTENS! My mama didn't play when I was a kid and she don't play forty years later. I remember one time my mother told me to turn my music down. I turned it down a little thinking it was enough to satisfy her request when, out of nowhere, I see her foot crashing through my door, slamming it open, and yelling at me "turn that moth@fu%$#$ music down!" It's funny to recall that now, but when it actually happened it was one of the most terrifying things I had ever seen. What made it so scary was, my mom doesn't curse, so bringing her to that much rage was eye opening and extremely unsettling. My friend who was in the room with me, would not leave my house by going out the front door. He didn't want to walk past my mom to exit the house so he jumped out of my window.
I am certain you can stop any Black man and ask him to share a memory of his mother disciplining him and he will be able to give you many stories of his mother "snapping" and tearing his ass up.
Speaking for most Black men in general, we have a healthy respect for the women that raised us, which is why portraying them is funny. For one, the portrayal of a Black woman by a Black man is his interpretation of what he witnessed and experienced growing up. It is also a way to safely "make fun of mama" without getting your ass whooped. Plus, Black men know that the next Black man can relate to the role because more than likely their own mama's have acted in similar fashion at some point in their lives. Though most of those portrayals aren't very flattering, I believe they were all created out of the love a son has for his mother.