7. Dennis Dugan
Filmography:
Problem Child, Brain Donors, Happy Gilmore, Beverly Hills Ninja, Big Daddy, Saving Silverman, National Security, The Benchwarmers, I Now Pronounce You Chuck & Larry, You Don't Mess With the Zohan, Grown Ups, Just Go With It, Jack and Jill If you make a career directing Adam Sandler movies then there is a good chance you are going to end up on a list like this. Dugan is responsible for such things as Jack and Jill, Just Go With It, Grown Ups, You Don't Mess With the Zohan, Big Daddy and so on, the list of terrible movies directed by this man is endless. Every single one of Dugan's movies is a massive stinker, yet he has grossed over $1 billion at the box-office, mainly because of the mystifying popularity of Adam Sandler, who has never done anything worthy of recognition outside of Paul Thomas Anderson's Punch Drunk Love. Dugan is as prolific as any director working in the mainstream and he had two big movies out in 2011. Sadly, those two movies were Just Go With It and Jack and Jill, the later of which stars Sandler twice. As a boy and a girl. Hilarity, of course, ensues. As well as his collaborations with Sandler, Dugan has dabbled in television where he directed episodes of Columbo, L.A. Law and Ally McBeal and also directed Problem Child, another horribly unfunny movie. Dugan has no concept of being able to set up a joke, unable to make use of Sandler's limited talent and each one of his films are a trudge to the end as his poorly directed movies cause more pain than laughs.