TYLER PERRY AS MABEL “MADEA” SIMMONS IN DIARY OF A MAD BLACK WOMAN (2005) MADEA'S FAMILY REUNION (2006), MEET THE BROWNS (2008), MADEA GOES TO JAIL (2009), AND I CAN DO BAD ALL BY MYSELF (2009)

Reason for cross-dressing: There is no apparent reason for Tyler Perry to play this matriarch.
Complex says: Tyler Perry is as polarizing a black actor as you can get. Black women love his work (which is kind of ironic, since his playing Madea takes one more role away from a black actress) but outside of that circle there have been numerous critics of his programs. We won't say it, but Spike Lee’s ether a couple of years ago sums up the criticism pretty nicely. Still, Perry has made himself a fortune with Madea. You can always buy self-respect, right?

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