Continuity mistake: During one scene in Camryn's Halloween birthday party (where she is wearing a silver mask), it is actually Tia playing this role instead of Tamera.
Factual error: The movie is supposed to take place in and around New York City, however during the car chase where Angelina and Brad are fighting off the three BMW's, a wide shot clearly shows a street sign announcing Los Angeles.
Other mistake: In the beginning of the song about Augustus Gloop, computer generated Oompa Loompas can be seen running through the Chocolate Room, preparing to sing their song. In the DVD release, some Oompa Loompas can be seen running to places that no real person could possibly stand on. This mistake was later corrected in the Blu-Ray release.
Continuity mistake: When Adam Sandler reverses into the police car, he damages the Bentley he is driving at the back end. When the police chase him, the back end is not damaged at all. (00:06:35)
Character mistake: In the scene where Steve and Josie prepare to leave to fight the giant robot at the beginning of the movie, Steve tells Will "Oh, Will, a reminder: a lot of the kids at Sky High will only have one super hero parent, not two." When he says "one super hero parent", he holds up two fingers. When he says "not two", he holds up only one finger.
Continuity mistake: In the scene where Vince Vaughn is complaining to Harvey Keitel in Harvey's office about the hitman he hates his gold necklace is either tucked into his shirt and red tracksuit or hanging out. This alternates throughout shots but during the same conversation.
Visible crew/equipment: When Shane is talking to Mrs. Plummer before she leaves, throughout the scene the camera man is reflected in her window (he is in black, not to get confused with Shane's white shirt) and as the car drives away the camera is shown backing up in the black door.
Continuity mistake: Look at the dirt when Herbie backs away from the nose of the newer Beetle, between the races out in the desert. Although Herbie drove straight up to the newer Beetle, tire marks can be seen where the crew moved the car back and forth to get him lined up.
Continuity mistake: When Vanessa is outside of the beauty shop playing her keyboard with her headphones, and Willie is talking to her, she takes off her headphones and puts them around her neck. In between shots the headphones disappear.
Continuity mistake: After Casey has turned down Harvard and is skating on the pond, she falls many times. When she falls for the fourth and final time, her hat falls off. In an overhead shot, the camera even shows it laying on the ground above her head. When she gets back up upon seeing Teddy with the zamboni, her hat has disappeared. (01:12:05)
Continuity mistake: After Evangeline has left with Aunt Adelaide, Nanny McPhee enters the children's room, and as she and Chrissie walk to the bed they pass Eric's, Lily's and Tora's beds, with the bare wood floor at the center - there is no rug. However, when Nanny McPhee leaves their room the long red and white rug is at the center of the floor, between all the beds. (00:51:55 - 00:52:55)
Continuity mistake: Throughout the movie Bailey's hair gets longer and shorter.
Continuity mistake: After his father's funeral, when Drew turns on the ignition and in following shots, the leather band that he wears on his right wrist (not the watch) is clasped with its strap facing his thumb, yet when he passes the sign for 60B, the band goes round the opposite way. Then, when he listens to The Hombres the leather band is flipped back, but when he picks up Global Business Today magazine it's switched yet again, and so on. (01:43:00)
Continuity mistake: In the scene when the Sherminator is talking with Matt after returning from band camp, Matt is wearing a purple shirt. But when Matt asks if "everyone hated his brother", in the reflection of the star trophy on the desk, you can see Matt's reflection, and he is wearing the orange and black striped shirt from the earlier scene where the Sherminator sends him to band camp. Clearly the two scenes were cut together. (01:21:50)
Continuity mistake: Why and how would/could Sara dry clean and return Hitch's shirt when, in the process of it being trapped in the cab door, you could see and hear it being ripped to shreds? (00:40:00)
Continuity mistake: The Tina Turner wig that Sam is wearing changes between scenes. In the traffic jam it is noticeably more spiky than the one she was wearing in the drag club. (01:20:50 - 01:31:00)
Continuity mistake: When the car blows up at a rest stop, when the children run to Ice Cube, the boy is on his left. However, when they turn around and sit, the boy is on his right.
Other mistake: It was established in the first Mask that the mask does not work in the daytime, but it works during the day in this movie.
Factual error: When Debra Messing and Dermot Mulroney 1st arrive in London Debra goes to a pub to change her outfit, the shot showing the outside of the pub you can see an American style traffic lights eg walk, don't walk which are nothing like the English green man red man traffic lights.
Suggested correction: The movie takes place over the course of several months, of course her hair changes length. Therefore not a continuity error.