BRANDON T. JACKSON AS CHARMAINE DAISY PIERCE IN BIG MOMMAS: LIKE FATHER, LIKE SON (2011)
Reason for cross-dressing: Jackson, who plays Lawrence's son, witnesses a murder and must disguise himself as Big Momma's niece to hide from his would-be murderers. Complex says: Brandon T. Jackson is black and has a nice blossoming career going for him, so it was inevitable that we catch him in a dress. Now here's the sick shit: No matter how terrible this movie looks (and really, just take a glance at that trailer) you know it's going to be a hit. Why? Because the first two were huge. Which just tells us this shit will never stop.