Happy Gilmore: Happy Gilmore is a classic Sandler comedy that never gets old. The emotional Happy Gilmore is constantly trying to get a shot at professional hockey with no luck, and he inadvertently discovers he can hit a golf ball over 400 yards. Happy, with some training from former PGA-pro Chubbs Peterson, works his way into the PGA tour and defeats the infamous Shooter McGavin in the biggest golf tournament. Happy Gilmore never fails to make one laugh. Happy's ridiculous anger-fueled shenanigans are unlike anything the upper class country club members have ever seen before, which leads to many more laughs as well.
Grown Ups 2: Although Sandler is included in my best and worst movie, it's not completely his fault. Grown Ups 2 is the absolute worst movie ever created. There is absolutely no plot to the movie, it basically just follows up on the lives of the character from the original. There are little to no laughs, and the "funny" scenes will maybe make you chuckle, definitely don't expect your sides to be hurting. They also put Shaq in the movie for some added fame, and he is awful. Just awful.