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Revealing mistakes
After Happy knocks Chubbs' wooden hand off with the hockey stick, Chubbs' right hand is clearly visible.
At the beginning when Happy is playing hockey, he hits the puck at the glass which the two coaches are standing behind. The glass clearly gets broken but then in the next close-up shot of the two coaches, the glass is back. A reflection can be seen in it.
Happy's Plymouth Duster has a sunroof when the lady from the nursing home jumps on the hood. In other scenes the sunroof is missing.
When Happy is in the batting cages, Chubbs pulls the plug for the pitching machine causing it to stop. The cable is visibly unplugged in the next scene but when the young boy enters the cage the machine still works.
On the first day of the gold jacket tournament, you can see Donald's VW Bug already lodged against the TV tower, but the car strike incident occurred on the fourth day.
When Happy is signing the woman's chest, the 'Gilmore' section of the signature moves from one side of the chest to the other.
In the final round of the Tour Championships, Happy takes about 6 swipes at his ball in the rough, and when he does finally make contact the ball lands in water. Each swipe should be counted as a stroke, as well as a penalty stroke for the water hazard. Yet, Happy only loses one stroke to McGavin.
When it comes to unpaid property taxes it has nothing to do with the IRS, it is a county assessor issue. If the IRS has unpaid income tax they would not seek to sell your house you are living in to pay the debt.
During the tournament with Bob Barker, there is a person in the gallery making distracting comments during Happy's swing. This would never be allowed during a tournament. They would have been thrown out of the course for making comments.
At his first tournament Happy "addresses" the ball on hole 1, swings, and misses. This counts as a stroke, but on the leader board on 18 it shows he got a hole-in-one on hole 1. This kind of mistake is made repeatedly throughout the movie.
Fans are not allowed on the course during a pro golf tournament nor are they allowed to talk to the golfers. This fact is ignored frequently in the movie.
Shooter has a chip shot where he is in the rough with very little green to work with. His caddy recommends he use a 5-iron. It is not unusual for a skilled golfer to use a club with very little loft in order to hit a "pitch and run" shot instead of a "flop and stop" shot. Commonly, 7 or 8 irons are used around the green frequently for this purpose. 5 irons less so, but not unheard of.
You may grip a club as close to the clubhead as you wish as long as you make a correct stroke (no "sweeping" or straddling the line on the green). This is done frequently to "shorten" a club with less loft (for example) to hit a low shot (in wind, etc) with less distance, i.e., "choking up" on a long iron to hit a short shot with a full swing.
After Bob Barker throws Happy in the water, they roll down the hill together. When they reach the bottom, both are completely dry.
It may seem like they are both dry. But Happy is still wet when Bob Barker is punching him. The back of Bob's pants are wet, as you can tell when he walks away.
During the opening scene for the tour championship. The Volkswagen bug can be seen against the tower. That scene is not until the end of the movie.
When Happy putts the ball too far and it rolls back into the hole, the groove carved in the ground to direct the ball is clearly visible.
When the movers are at Grandma's House, they bet that Happy can't hit the ball. After he swings, the ball can be seen being pulled back through his legs, under the grass. This is visible throughout the movie in several spots.
When Bob Barker and Happy Gilmore are rolling down the hill, at the very end of the shot, you can see Bob's stuntman's face.
Obvious knee pads on the IRS agent Happy throws through the door of his grandmother's house.
No one would have been allowed to climb the tower, at any time, except television employees.
The opening scene shows an old couple looking down at the broken lens of the camera, but the broken glass is laminated and couldn't be the lens of the camera.
The scoreboards through out the entire movie are incorrectly showing the scoring for the players.
The opening scene shows the slap shot which supposedly killed Happy's father. You hear the slap, then the glass breaking, and the camera falls but with out any break in the glass.
The car that crashed in to the tower would have been removed before play would have continued. The tower would have been repaired also because it had a camera and an employee on it.
When Grandma is dressed like Gene Simmons from Kiss, she is wearing a mask with makeup. The band members did not use masks or makeup in 1996.
Shooter McGavin was beaten up off-screen when it clearly should have been seen.
At the bar after the first tournament, when Happy says "I was on this tour for one reason: money" when the camera shows the back of his head, his mouth is not moving.
The flag in the background in the office at the Portland, Oregon, Open is a Washington State flag.
At the Michelob Open, a sign for the Visa Everglades Open is visible in the background.
After his fight with Bob Barker, Happy has a disciplinary meeting with Doug Thompson where he learns of his suspension. In a meeting like this, no other player would be present unless they were involved in the incident. Shooter McGavin would have no reason to attend this meeting, but he is present and reacts to the decision being made.
The IRS doesn't process unpaid taxes in this manner. The IRS would normally try to reach out to the individual over several years. There would be notices, hearings and attempts to setup payment plans, grant hardship extensions or setup payment plans. Foreclosure is the very last option.
When Happy tries to win back his ex girlfriend Terry and sings Til the Night Closes In on the intercom and a strange Asian lady comes to Happy's door. How does the Asian lady know which apartment Happy was in? And how did she get in the building without being buzzed in?
At the AT&T Open, Shooter asks his caddy for advice, the caddy gives it and Shooter ignores it by choosing a different club. Right before Shooter takes his shot the caddy moves forward and to the right, which places him directly in Shooter's eye-line. This would never happen - all caddies know they must stand behind the golfer as to not obstruct him.
Happy's golfing attire on several occasions does not meet the standard dress code for professional golf and would disqualify him from participation.
During the AT&T Invitational, Shooter chips in a putt and ultimately fires his caddie for club choice. However, when Shooter makes the winning putt on 18, that same caddie is seen behind him happy that Shooter won. Not only that, but Shooter's caddie is also tending the flag when he makes the putt. Then when the camera goes on shooter "shooting his gun" again, the caddie is behind him.
Shooter's caddy recommends he uses a 5-iron for a particular shot. Shooter opts for his wedge, and chips the ball onto the green.
A 5-iron has a range of around 160-180 yards, and Shooter's caddy should have known this.
After Shooter McGavin invites Happy to the ninth green at 9pm as a gag, he quickly looks at the camera for a fraction of a second when he turns toward it.