Continuity mistake: At Happy's first tournament (the one he goes to with Chubbs), when Chubbs does the 'it's all in the hips' motion there is a lake behind him and Happy. However, when Happy then hits his ball and we see the overhead shot from the ball's point of view, we can see that there's no lake anywhere near them - it's just a green fairway.
Continuity mistake: A number of time when Happy is Teeing of if you watch closely the ball actually goes through his legs not straight ahead.
Continuity mistake: Towards the end in the championships,when Happy swings, his shirt comes up and his stomach shows. The next time, you can see a grey shirt tucked in underneath. Then later, there's just his stomach again.
Continuity mistake: When Happy drives the ball down the street and it hits a house the golf club is resting on his shoulder. A second later he is leaning on it.
Continuity mistake: When Happy is confronted by the IRS man, and is told about having to give up the house, the folder in the IRS guy's hands keeps switching hands from shot to shot.
Other mistake: When Happy Gilmore and Chubbs are at the miniature golf course whenever the ball comes back no one stops it or puts it back in its spot yet it is there every time.
Continuity mistake: In the scene where Shooter is with the other pro golfers, (the ones with the gold jackets) and they're drinking wine, Happy interrupts them wearing an ACDC top. Notice Shooter's wine glass switch hands a number of times, and when he tells Happy to meet them on the 9th green, the wine glass has disappeared totally.
Audio problem: After Shooter calls Happy a freak, there's an over-the-shoulder shot of Happy saying that he entered the tournament for one reason. As he says this line, his mouth doesn't move.
Continuity mistake: When Happy hits the AC in the window it has bigger sides to fill the window space. When the AC falls on the Mista Mista lady the extra sides are gone.
Continuity mistake: When Happy punches Bob Barker for the first time, Bob falls down a few feet away from Happy. You can see him start to get up almost immediately. But, in the shot of Bob from the front as he's standing up, he's much closer to Happy than he was in the previous shot.
Other mistake: When Bob Barker reaches up to grab Happy by the neck, his head is resting on the grass immediately before and after that shot. Happy was standing fully upright, so there's no way Bob Barker's arm could have been that long.
Suggested correction: Happy isn't standing. He's kneeling. You can see him stand after Bob grabs him.
Factual error: Since the tower became a movable object by collapsing it would be considered a movable obstruction. According to rule 24.1a of the PGA Rule book. Happy could have waited for the obstruction to be cleared then putted.
Plot hole: The bet between Happy and Shooter is prohibited, probably legally, but also definitely according to PGA regulations. It is prohibited for any professional athlete to gamble, on their sport in general and certainly on their own performance. Both of them could get suspended or banned from Pro Golf for this, and Shooter would certainly know it (there is room for Happy Not Knowing though, as he of course has never gotten particularly far in even his favorite sport).
Continuity mistake: The wound that Happy gets in his fight with Bob Baker becomes larger and fresher when he is in the subway place, and the next day the wound is gone.
Continuity mistake: While Happy is talking with Shooter and Virginia at the house auction, the sun is changing between shots.
Continuity mistake: When Happy wins the 3 in a row shot bet with the two guys, the sun changes between shots.
Continuity mistake: When Happy makes his last shot and wins the golden jacket, the sun changes between shots.
Continuity mistake: On the last hole, Shooter McGavin overshoots the hole and the ball ends up going past the green. However once he shoots the ball off the man's foot and onto the green, we now see him coming onto the green from the fairway side at the bottom of the screen, not from behind the green past the hole.
Continuity mistake: When Mr. Larson bends Shooter's golf club, he's holding the head of the club in his left hand. When it cuts to a shot behind him, the club's head is in Mr. Larson's right hand. When they show him from the front again, the club head is back in his left hand.