Ranking Adam Sandler's 23 Films From Worst to First

By Dustin Rowles | Lists | November 10, 2011 |

By Dustin Rowles | Lists | November 10, 2011 |

Adam Sandler’s Jack and Jill arrives in theaters tomorrow, and with any other A-list actor, you look at that trailer and you immediately think, “That’s got to be the worst movie he will ever star in.” How could any movie be as bad as Jack and Jill looks? And how the hell can Al Pacino not only show up in the movie, but play himself. Play himself in love with a man dressed up like a woman? A woman that looks like Adam Sandler. Jack and Jill looks like a new low, the booger on the face of American cinema.

But then again, I wonder how it could possibly be worse than the last ten movies on this list, which ranks Sandler’s oeuvre from worst to best, a list that includes six good movies, three decent movies, there more watchable movies, and ten movies I wouldn’t force on my worst enemy, and right about now, that’s Adam Sandler. It’s like he’s daring himself to to see how bad a movie he can make before audiences stop showing up.

It’s worth noting that these 22 movies also made $1.8 BILLION at the box office, and nearly $3 BILLION worldwide. Note, too, that only movies in which Sandler played lead are included.

23. I Now Pronounce You Chuck & Larry

22. Grown Ups

21. Just Go With It

20. Little Nicky

19. You Don’t Mess with the Zohan

18. Bedtime Stories

17. Eight Crazy Nights

16. Click

15. Mr. Deeds

14. The Waterboy

13. Bulletproof

12. The Longest Yard

11. Anger Management

10. Reign Over Me

9. 50 First Dates

8. Airheads

7. Spanglish

6. Big Daddy

5. Billy Madison

4. Funny People

3. Happy Gilmore

2. Punch-Drunk Love

1. The Wedding Singer