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Adam Sandler Comedies: The Good, The Bad, The Ugly

One thing is for certain when it comes to Adam Sandler: love him or hate him, he makes movies that make money. You either jive with the immature goofy humor that changed the comedy landscape in the mid-'90s, or you find his movies pretty detestable. So for this week's edition of "The Good, The Bad, The Ugly," nothing could be more fitting on the eve of his new film Grown Ups than sorting through the highlights and low-lights of a pretty impressive comedy career.

I'm sticking with just Happy Madison Productions films. As always, feel free to state your case in the comments below for any of these films being moved into a different list -- or for the few I left out, feel free to place them.



Billy Madison (1995) – When I attended a sleepover in third grade and my friend said in astonishment “you’ve haven’t seen Billy Madison?” I had no idea that my concept of comedy was about to get flipped on its head. Having previously known few PG-13 movies, the opening scene of Sandler riding a golf cart and shouting in his patented child voice “it’s nudie magazine day!” was a revelation. This movie is quite possibly still Sandler’s best film even though it was his first major role. I also have yet to forget the Spanish Armada was in 1588.

Big Daddy (1999) – The average guy who can barely take care of himself having to take care of a kid was – for someone of Sandler’s talent – a stroke of genius. This film established early on his still-underrated ability to work wonderfully with kids. (If you need any further proof, check out Bedtime Stories.) Be it using newspaper to solve a bedwetting issue, ketchup for breakfast, kangaroo songs or Sandler taking innumerable shots at his ex who works at Hooters, there’s a lot that’s memorable about this film.

The Wedding Singer (1998) – One of my personal favorites, The Wedding Singer is one of the few romantic comedies I’ve ever truly enjoyed and I didn’t even have to know the ‘80s all that well to do so. As you can tell by the interesting next film on “the good” list, I’ve always been impressed by the chemistry between Sandler and Drew Barrymore. Sandler’s song about his ex Linda is one of the top Sandler movie moments and “I Wanna Grow Old With You” is one of few rom-com “declaration of love” moments I haven’t rolled my eyes at.

50 First Dates (2004) – I’m normally a steel trap when it comes to having a bias toward certain films, but I still manage to have a soft spot for any movie that has an interesting twist on time. Such is the case with this movie, which is in large part why I enjoyed it: Barrymore plays a girl with short-term memory loss: she thinks every day is one specific day because she can’t remember anything that’s happened when she wakes up the next morning. The comedy comes when Sandler tries to court her anyway. Concept aside, Sandler is sweet in this film as well as funny (like when he makes asides to his walrus friend) and Sean Astin as the lisping steroid-popping brother to Barrymore’s character is one of the more unique supporting characters in a Happy Madison film.

Happy Gilmore (1996) – Because this film is viewed as part of the one-two punch with Billy Madison that started Sandler’s film career (hence Happy Madison Production), “Happy” stays on my “the good” list. There’s nothing all that wonderful about the film: Sandler plays a bad ice hockey player who becomes a golf phenom with a penchant for anger, but with the memorable Bob Barker fight on the golf course and brilliant quotes from Christian McDonald’s heinous Shooter McGavin, there’s a bit of fond Sandler movie memories in this film.




You Don’t Mess with the Zohan (2008) – The concept was a bit out there for this recent Sandler movie, which I actually quite enjoyed, but I’m one of few audience members who understands the Israeli sense of humor that Sandler milks quite a lot. He plays an Israeli Moussad agent named Zohan Dvir who dreams of nothing but coming to America and cutting women’s hair. With a side plot involving Lebanese terrorists, “Zohan” spins slightly out of control, but it was interesting to see Sandler try an entirely different persona.

Click (2006) – First off, Sandler in real life is not capable of landing Kate Beckinsale – but I’ll save my rants on average guys with smoking hot wives in film/TV for another day. Basically, I’ve never been left more comically confused after a Sandler movie than I was with Click, which tried to combine immature Sandler humor with some emotional lessons and about family. The concept of a remote that does to real life anything a normal remote would do to a TV was pretty solid and it gets some laughs through much of the film. But as the movie goes on, suddenly there are these emotionally intense scenes. Sandler’s brand of immature guy humor is oil and the sensitive family stuff is water. They just didn’t work together.

The Waterboy (1998) – It’s hard for me to demote any ‘90s Sandler movie to “the bad” list, but when you think about it, this movie is exactly like Happy Gilmore in numerous ways: a guy who lives with his mother/grandma who has random anger outbursts competes in a sport no one suspected he would be any good at. The difference is that Bobby Boucher used Sandler’s itty-bitty child voice and was twice as dumb. For those who despise Sandler’s style, this has to be their primary piece of evidence, because no film tries harder to exploit Sandler’s immaturity style and goofy anger than The Waterboy. On the plus side, Rob Schniedier shouting “you can do it! … you can do it ALL NIGHT LONG!” entered modern slang more easily than any other Sandler movie quote.

Anger Management (2003) – Here’s another film that tries to use Sandler’s angry humor to its advantage and hopes to then balance it with a star that has wider appeal in Jack Nicholson. The main issue with “Anger” is that there’s virtually nothing I remember about this movie other than “guzfraba,” which for me and most Sandler fans is a rarity for a Sandler film.




The Longest Yard (2005) – Remaking the classic Burt Reynolds movie was just a poor choice on Sandler’s part. The film isn’t horrid and boasts a decent ensemble that includes Reynolds, Chris Rock and the impeccable James Cromwell as the prison warden. However, most of Sandler’s success has come from originality and creativity in plot and characters, which The Longest Yard has none. Sandler plays a pro quarterback who falls into obscurity after throwing a game to win a bet, hits a rough patch and ends up in prison where he’s asked to coach a bunch of convicts to play football against the prison guards. We’ve seen him do sports and the character provides Sandler no challenges: he’s supposed to be “the normal guy” and the convicts are the goofballs.

I Now Pronounce You Chuck and Larry (2007) – All the concepts for Sandler’s movies had pretty much steered clear of major issues, but suddenly this movie comes along and exploits homophobia for some laughs in a movie about two firefighters pretending to be partners so one can get pension benefits for his family. I consider myself open to all kinds of humor both politically correct and not so much, and I laughed at this movie plenty, but not without feeling odd about it. There’s a message in this movie, but it is most at odds with the humor. Not everyone will see it that way and enjoy this classic Sandler-style comedy, but the conflicting ideology was unexpected to say the least and the film mediocre minus Jessica Biel’s gorgeousness.

Mr. Deeds (2002) – Another example of Sandler trying the remake thing to mediocre results in this update of the Frank Capra classic Mr. Deeds Goes to Town starring Gary Cooper. I can understand his interest: an average guy finding out he’s now the majority owner of a major company is very Billy Madison-esque, but like all below-average Sandler movies, there’s nothing memorable about this film except John Turturro as the butler Emilio.

Little Nicky (2000) – When I heard from someone that Little Nicky was bad, I was in a state of shock. I’d loved or enjoyed everything Sandler had done up to that point and “Nicky” was Sandler’s first bad apple. The reasons are easy to see in hindsight: the supernatural fiction angle with Sandler playing the black sheep/runt son of the devil was way to out there and absurd despite some great names in the cast including Harvey Keitel and Rodney Dangerfield. You can see why Sandler only played normal human characters from that point on.


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