And right when it seemed like things were taking a dip, with four sub–$100 million grossers in five years, between 20, he signed a four-picture deal with Netflix that turned into an eight-picture deal that let him continue with even more freedom. He’s never had to waver from this approach because of his continued success. He’s worked with the same few guys over and over - Frank Coraci, Steven Brill, and Dennis Dugan have combined to direct 17 Sandler films - and he’s famously, and increasingly over time, filled the cast with friends and past collaborators. Since The Wedding Singer, he’s hand-picked the directors (and often, according to an interview with Norm Macdonald, essentially co-directed).
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Excluding some early work and the straight acting gigs with more serious directors, Sandler has written or rewritten essentially every movie he’s been in (though he often doesn’t take a writing credit) and served as an executive producer on all of them since The Waterboy. The thing I ultimately came back to when approaching this list is that Sandler has had an unprecedented amount of control over the movies he has made. (I also wouldn’t say the popular opinion is constantly right this is not a list in order of box-office gross.) Film critics are judging Adam Sandler’s movies against every movie this list is about judging them against themselves.
Though I clearly disagree with the critical consensus on specific movies, I wouldn’t say they are constantly wrong. The difference is that when Sandler makes (as in, stars in and produces) a movie, it’s exclusively big and dumb. That disconnect isn’t unique to Sandler - from the Three Stooges to Jerry Lewis to Mel Brooks to Jim Carrey (save Liar Liar, oddly enough) to MacGruber, there’s been a lot of great comedic work beloved by many but not by reviewers at the time of release. Film critics are in the business of being (and seeming) smart, and that is at odds with Sandler’s intent as a filmmaker. This split arguably stems from the type of movies Sandler chooses to make - big, dumb comedies. It’s the dichotomy that has followed Sandler his whole career: The critics hate him, but audiences love him. Sandler, who in 2019 marks 30 years of making movies, has 11 Razzie nominations for Worst Actor and 11 acting nominations from the People’s Choice Awards. In the same time period, only two movies that he’s starred in and produced have received higher than a 50 percent score on Rotten Tomatoes - Happy Gilmore and The Wedding Singer (though both are inflated by extremely positive DVD reviews). That’s more than Ben Stiller more than Jim Carrey more than Will Smith more than Tom Cruise. How do you reckon with a career as polarizing as Adam Sandler’s? If you account for inflation, the 55-year-old zhlubbyman comic actor has starred in 18 movies that have each grossed more than $100 million worldwide, beginning in 1995 with Billy Madison. This article was originally published in 2019 and has been updated to include Hustle, Adam Sandler’s latest film.
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