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The Five Worst Adam Sandler Movies

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Comedian, actor and former Saturday Night Live star Adam Sandler became one of the biggest comedy film stars of all time thanks to a run of box office hits running from the mid-'90s through today. Unfortunately, his career is an example of the law of diminishing returns -- his films have continued to get worse and worse over time. Despite their success, Sandler is responsible for some of the worst comedies of the last 20 years. Here's the bottom of the barrel.

1. Jack & Jill (2011)

© Sony
For several years straight, every movie Adam Sandler released was his new worst movie. The streak culminated with 2011's Jack & Jill, still the nadir of Sandler's filmography and one of the worst comedies of the decade. Sandler plays a pair of twins in a comedy so stupidly "high concept" audiences thought it was a meta-joke -- that Sandler had actually made one of the stupid movies he parodied so well in Judd Apatow's Funny People. Nope. We were meant to take Jack & Jill at face value. And for those of us that sat through it, the scars have yet to heal.

2. Grown Ups (2010)

Grown Ups DVD box art
© Sony Pictures Home Entertainment
Sandler's gradual decline into lazy complacency is best personified in his 2010 comedy Grown Ups, a filmed vacation for him and his friends paid for by the American movie going public. With an all-star lineup of Sandler's friends (and Happy Madison stars) including Chris Rock, Kevin James, David Spade and Rob Schneider, Grown Ups should have been enjoyable just for the time spent in this company. Instead, it was lazy and stupid at every possible turn. The height of the film's comedy involved an elderly woman farting. Naturally, it was a big enough hit to spawn a sequel in 2013.

3. Click (2006)

Click DVD cover art
Photo courtesy PriceGrabber
Adam Sandler's movies always have a tendency to get bogged down in mawkish sentiment, but no movie in his filmography is guiltier of this than Click. What begins as another terrible high-concept comedy about a guy who finds a remote control that can be used to control his real life slowly morphs into a sickeningly "touching" story of a guy who grows old and regrets his entire life. What? Are we really supposed to cry for Adam Sandler in bad old age makeup moping because his kids don't love him? In the stupid remote control comedy? Needless to say, thevhalves don't mix. Neither half even works on its own. Here's a Sandler movie that finds two ways to be bad.

4. I Now Pronounce You Chuck and Larry (2007)

I Now Pronounce You Chuck and Larry DVD cover art
© Universal
Sandler teamed with his friend and fellow comedian Kevin James for the first time for this repellant "issue" comedy that probably set gay rights back a couple of years. Sandler and James play firefighters who pretend to be married for the insurance benefits, giving them both lots of opportunities to traffic in ugly stereotypes (several of them courtesy of frequent Sandler collaborator Nick Swardson in a supporting role) and bug their eyes out at the thought of doing anything "gay." By the end, of course, the movie tries to preach a message of tolerance, but it's neither earned nor sincere. After nearly two hours of making jokes at the expense of the gay community, it's too little too late.

5. The Longest Yard (2005)

The Longest Yard DVD cover art
Photo courtesy PriceGrabber
Remaking the gritty 1974 football movie starring Burt Reynolds, Sandler and company try to turn The Longest Yard into a broad comedy. Mostly, though, they just keep the beats of the original movie and add a bunch of stupid jokes about a horny old lady (Chloris Leachman) and an effeminate inmate played by Tracy Morgan. This is a Sandler movie that satisfies no one: too jokey to be a satisfying sports movie, too serious to satisfy comedy fans. Between this and Mr. Deeds, hopefully Sandler learned that turning old movies into Happy Madison comedies does not a good movie make.
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