Goofs

When being told of the challenge, Monty closes the case that holds the Million Dollars and locks it. No one re-opens it, but just before he leaves the office, it is shown open again.

When Spike makes a profit of 10 million, Brewser ask to be alone. When they walk out the door closes and in the next frame they open the door and you hear the door close again.

On the cover of USA Today it shows a picture of Monty Brewster in front of a podium with his "None of the Above" slogan. The article was to highlight the Yankees exhibition game, and before Brewster had decided to start his mayoral campaign.

Brewster agrees to the deal with the limitations that he can't give the money away. Within 7 minutes he asks 20 strangers in a group at the front of the building if they want to go to lunch, on him. That's giving it away. He shouldn't have gotten the 300 million.

At the end of the movie, Monty needs to spend $20,000 and gives it to Angela as a "retainer." A legal retainer is essentially prepaying for legal services. This would be considered an asset and so Monty would have not met the will requirement of not having any assets.

Monty is told Rupert was his great-uncle but then after the film starts, Rupert tells him that he is Montys great-grandfather.

However, this information isn't presented as fact; it's just a character error.

It is often claimed that by using the rare postage stamp to mail a postcard Monty violated the clause of the will forbidding destruction of inherently valuable property. However, as Monty was using the stamp for its originally intended purpose this would not go against the terms of the will.

In the opening baseball scene when Brewster is facing Rudy, he is wearing a batting helmet with ear covers over both ears indicating he is a switch hitter. When facing Brewster, a right handed pitcher, he is batting right handed instead of left handed which would have been to his advantage. However, as with even lower levels of play, in the minor leagues there is certainly not always the luxury of having a single-flapped helmet for each batter and often non-switch-hitters end up wearing two-flap helmets as well since those type are often the ones carried most by teams since they can be used for right-handed or left-handed batters.

Warren says he wanted to meet Brewster "mano to mano", meaning man-to-man. But "mano" is the Spanish word for "hand". This is to illustrate Warren is self-important and not as smart as he thinks.

However, this the above explation is incorrect. "Mano a mano" is a Spanish phrase. Whilst the direct transaction is "hand to hand" it's commonly used to mean "man to man". It describes a situation where two people are competing, fighting, or arguing directly with each other. Warren is using the term correctly.

Toward the end of the movie in the boardroom, when Warren is talking and says "a couple of rabbits" the bald side of his forehead is on the left. When he talks again, you can see the bald side of his forehead on the right flipped around. The next shot of Warren it returns back to normal. It takes place all within a few seconds.

When Brewster is asked to go into the board room at the beginning of the film they first call him Mr Rooster and then Brewster each time after. Even the subtitles reflects this.

In the opening scene, they're supposedly playing at Hackensack New Jersey's home field, but the wider shots clearly show mountain ranges beyond the ballpark.

The train that cuts through the outfield of the Hackensack stadium says "The Pine Tree Route", a slogan for the Maine Central railroad.

Monty wakes up at 3pm (according to the concierge), changes his clothes and checks out of his hotel shortly after 3pm the last day of his bet. He shows up at Granville and Baxter just before midnight, but there isn't an explanation of where he was in that 8 1/2 (or so) hours.

However, just because something isn't explained it doesn't make it a plot hole. His whereabouts during this time are irrelevant to the plot.

(at around 19 mins) The tip of a boom mic is visible.

The shadow of the boom mic can be seen moving on Salvino's left shoulder during the meeting with Heller.

The stamp dealer who sells Monty the rare "Inverted Jenny" stamp claims that "of the one hundred of these stamps originally printed, this is the only known copy in existence." In fact at least 90 specimens of the "Inverted Jenny" are known to survive in the hands of collectors.

When Monty runs for mayor of NYC, the lawyers say that he is running TV ads in all 52 States. There are only 50 States in the USA.

In the courtroom scene the judge says, "So you were making advances to a woman who was clearly involved with another man," however, in Monty and Spike's previous statement just before she said that, they both clearly stated that they did not know the woman had a fiance. Even though their statement was untrue, the judge did not know that at that moment.