The movie takes place over a "few days" while Chuck gets the paperwork signed to get Deeds his money. When Chuck and Cecil pick Deeds up from his hometown to take him to New York, the helicopter lands on bright green turf and folks in town are wearing summer clothes. By the time Deeds leaves New York a short time later, it's winter. Ponds are iced over and the snow is thick on the ground, as if it has been winter for some time.
When Deeds first shows up at his mansion there is no table between the staircases in the "echo room", but the next day it is there when he slides down the banister, breaks the table and finds the journal.
The hidden camera on Pam's sweater keeps disappearing/reappearing throughout the scene before the cat rescue. Also, while trying to capture the rescue on film, Pam indicates that it is in the flower, when in fact it was shown in the middle of her collar in earlier shots.
While Pam/Babe is making her speech at the end, her hair parts from one side to the other and back between shots, and her mic switches hands. The middle shot was apparently flipped to maintain direction of movement during the sequence.
In the beginning of the movie when Anderson and Chuck are talking to Deeds inside the town's bar, Anderson's scarf goes from inside his overcoat to outside his overcoat several times. Later on the street while talking with the older ladies, Chuck's scarf is straight, then is twisted in matter of seconds.
After Deeds hands the Oreo and french fry pizza through the jail window to Crazy Eyes, he is immediately shown holding a slice and biting into it. He did not have enough time to put the pizza down, open the box, and take a slice.
Preston Blake is airlifted from the top of Mount Everest - around 29,000 feet - above the maximum altitude possible for most helicopters (the air is too thin). No helicopter was able to reach the top of Mount Everest until 2005.
When Deeds is rescuing the cats, he saves a few before the characters stop in front of a stove and say that there is only one cat left. As the characters are discussing this, there is a cat in plain sight on top of a stove behind them. They do not save this one, however, since the "last cat" they are talking about is the one on fire under a chair, not this one on the stove.
At the end of the movie, when the shares sale is annulled, Emilio Lopez gives Deeds one billion dollars, but Emilio receives the stock of his father and turns to be the major stockholder in Blake Media, but not cash.
The goof items below may give away important plot points.
At the end of the movie in the conference room, Emilio Lopez is announced the major stockholder in Blake Media. After Emilio fires Chuck Cedar, you hear Chuck exclaim, "You can't fire me!" However, Chuck's lips aren't moving to the words.
As Deeds drags Pam out of the ice hole she is soaked and dripping water everywhere. In the next shot as they talk beside the hole, she and her clothing are suddenly dry - except for slightly damp hair.
When the show that Pam Dawson works for exposes her as an undercover reporter they show two side by side photos one of her as Pam Dawson (the virgin school nurse from Wincheastertonfieldville Iowa) and Babe Bennett (the reporter) the second picture of her with black hair is just a still from earlier in the movie before she died and permed her hair.