White Chicks (2004)

Plot hole: In the scene where Tiffany is trying on clothes, the sales associate walks into the room unexpectedly, "Tiffany's" shirt is partially off. But the sales associate doesn't notice that she is actually black with fake breasts and a wig. (00:37:00)

Gary Day

Plot hole: Kevin and Marcus's plan is flawed because, if Kevin had to "valet" park the car and he used it to drive Denise to the house he would have to: drop her off, return the car as Kevin, and somehow change into the girl disguise on. Unless he dropped off the car with the girl disguise on, it would be impossible to do that unless he brought a bag with him. Also he would have to somehow travel to the club and get there before Marcus. (01:04:00)

Plot hole: Given that the FBI was constantly monitoring the Wilson sister's room with a camera outside the door, they would have seen Kevin leaving the room dressed as himself and recognized him.

jerimiah

Plot hole: Kevin and Marcus are supposed to be bringing Brittany and Tiffany to the hotel in the Hamptons. But they get into a car crash on the way and have to stop somewhere else. When at the stop, they tell the girls to stay in the hotel and they become the girls. The problem, when they get to the hotel dressed as the girls, the two men (Marcus and Kevin) are supposed to do the hand off to the FBI agents at the hotel. But they aren't even there because they are dressed up as the girls. How does the FBI go the entire movie without once contacting them and especially, how do the FBI agents accept the girls without the correct handoff from Kevin and Marcus?