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Top 10 Best Adam Sandler Movies

Top 10 Best Adam Sandler Movies (List) - With ClipsThe top 10 best Adam Sandler movies. Comedian. Actor. Musician. Singer. Writer. Producer. Swell guy (probably). The sum of all these parts makes Adam Sander who he is today; a much loved and much viewed working entertainer. He makes us laugh. He makes it look easy. There are few comedic actors when have been at the top of the box office for as long as The Sandman, so let’s appreciate this multi-talented dude.

10. 50 First Dates (2004)
Top 10 Best Adam Sandler Movies (List) - With Clips
50 First Dates (not to be confused with the similar-sounding 51st State starring Samuel L. Jackson) is the 2nd collaboration between the Sandman and Drew Barrymore after The Wedding Singer.

Set in Hawaii, Sandler is Henry Roth, a ladies man (!) who falls for Drew’s character Lucy Whitmore. After managing to romance her, he wakes up the next morning to find she has forgotten who he is and has no prior knowledge of the previous day’s events. Thus, his resolve to chase Lucy is tested to the maximum as what may have worked for him on a previous day might not work the next.

Dates looked to match the feel-good factor of The Wedding Singer and for the most part it works thanks to the obvious chemistry between its two co-stars (who reunited again in Blended, see 2014 Romantic Comedies Guide), and to the fantastic supporting cast – a staple that is common in Sandler films. Rob Schneider as Ula – Roth’s strange native friend and Sean Astin as Lucy’s lisping, steroid-abusing brother steal every scene that they are in.

Best Sandman Moment: Sandler has a Beach Boys-related breakdown…

9. Reign Over Me (2007)

Top 10 Best Adam Sandler Movies 2009 - With Clips
2002’s Punch-Drunk Love is widely recognised as Sandler’s first successful attempt at a serious role, but I’m not going to talk about that because Reign Over Me is better for several reasons.

The story follows Charlie Fineman (Sandler) whose life was ruined when he lost his family to the events of 9/11. He bumps into his closest and most successful friend from college Alan Johnson (played by the dependable Don Cheadle) and Alan tries to break through the people barriers that Charlie has put up.

The character he plays is very complex and very different from any character he has tackled before. Smart directing in Punch-Drunk Love meant that there wasn’t too much focus on Sandler during the difficult scenes but here, he lays it on the line and the camera is very much depending on him to give an excellent performance. The crux of the entire movie is how believable Sandler is as this deeply hurt, socially inept and depressed human being and he impressively pulls it off. As a performance, Reign could easily be considered Adam Sandler’s Tour De Force.

Best Sandman Moment: Sandler makes the shrink…

8. I Now Pronounce You Chuck & Larry (2007)

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I originally saw this movie while holidaying in the town of Orange in LA. I thought it would be interesting to go to a cinema in America and see how they react to Adam Sandler movies. I can tell you, a packed house did not stop laughing from start to finish.

Adam Sandler and Kevin James are Chuck Levine and Larry Valentine, two hardworking heterosexual New York firefighters. When they have a close brush with death, Larry realises that he’s risking his inheritance to his children by being a single parent. Instead, he cooks up a scheme where he and Chuck would enter wedlock and pose as a homosexual couple. However, they need to convince investigator Clint Fitzer (Sandler regular Steve Buscemi) that they are a genuine couple, while Chuck has to contend with his feelings for their hot, hot, hot female attorney as played by Jessica Biel.

There was some backlash over the portrayal of homosexuality in this movie, which was interesting to me as it didn’t seem that A) those who made the comments had seen the movie or B) realised that this is an Adam Sandler COMEDY where you’re not supposed to take things too seriously!

Sandler and James make a natural duo and are great at riffing off each other. There are lots of memorable scenes including Sandler getting a handful of Jessica Biel (how does he keep getting amazing scenes like this?!), Ving Rhames doing an amazing rendition of Whitney Houston’s “I’m Every Woman”… naked and Rob Schneider’s faux-Japanese vicar who is obsessed with circles.

Best Sandman Moment: Hell yeah!

7. Billy Madison (1995)

Top 10 Best Adam Sandler Films (List) - With Clips
Some regard this entire movie as genius. Others believe you have to be pepped up by 4 ounces of crack to enjoy it. The truth is somewhere in the middle – but I think all can agree that this is the movie that introduced Adam Sandler as a bankable leading man.

The Sandman is titular character Billy Madison, the heir to his father’s vastly wealthy hotel chain. The only problem is Billy is a lazy, immature, slack-off, pot-head who his lives day-to-day by way of swimming pools and nudie magazines. In order to prove his worth to his father, Billy has to complete his scholastic education from Grades 1 to 12 in 24 weeks.

Billy Madison is pretty much Adam Sandler playing one of his “retard” characters turned to the maximum. His childish antics and funny voices made him like the dirtier version of Jim Carrey, his speciality mostly dick and fart jokes. But again, what makes Billy Madison so endearing is that is so damn funny – I guess you won’t really know if you like this kind of comedy until you see it. But for me, there are some things in this movie that you can’t help but just laugh at it. Some of the scenes and one liners in this movie have taken on a cult status almost of their own.

Oh yeah, Shampoo is better than conditioner and O’Doyle Rules!

Best Sandman Moment: High School is baaaaaaaaad!

6. The Longest Yard (2005)

Top 10 Best Adam Sandler Movies (List) - With Clips
The highest grossing film on Sandler’s resume, raking in $190m worldwide, it’s fair to say that The Longest Yard could be the most popular Adam Sandler movie ever made. It’s only number 6 on my list though.

The Longest Yard is a remake of the 1974 Burt Reynolds film of the same name. Sandler is Paul “Wrecking” Crewe, a disgraced NFL quarterback who after a major dismeanour involving drinking and driving, is dumped in Allenville Penetentiary. Crewe finds himself among rough company where the inmates don’t like the fact that a famous celebrity is among them, except for one, The Caretaker (Chris Tucker). Prison Warden Hazen (James Cromwell) wants Crewe to help the Prison Guard (American) Football team in exchange for a shorter sentence. What Crewe has to do is form a team of inmates designed to lose to the Guards, instead, he sees it as an opportunity to get even with them.

The Longest Yard is the biggest box office success on this list because it’s the most accessible. It’s a sports movie, a prison drama, a remake, and it has a hip cast, with the likes of Chris Rock, some former NFL players in Michael Irvin and Bill Romanowski and a whole host of pro wrestlers including “Stone Cold” Steve Austin, Bill Goldberg, Kevin Nash, Dalip “The Great Khali” Singh and Bob Sapp. The tone of the comedy is more accessible too with Sandler playing the straight man for the most part and letting the craziness come from his co-stars.

One more thing, Terry Crews as Cheeseburger Eddy is definitely a highlight of the movie. He’s always great. He even made White Chicks watchable.

Best Sandman Moment: Sandman one-on-one with The Playmaker…

5. Happy Gilmore (1996)

Top 10 Best Adam Sandler Movies (List) - With Clips
[Happy breaks into a fight with former Price Is Right host, Bob Barker.]
Happy Gilmore: [to Bob Barker] “The Price is Wrong, Bitch!”

[Shooter McGavin taunting Happy…]
Shooter McGavin: “You’re in big trouble though, pal. I eat pieces of sh*t like you for breakfast!”
Happy Gilmore: [laughing] “You eat pieces of sh*t for breakfast?”
Shooter McGavin: [long pause] “No!”

And I could go on…!

Happy Gilmore (Sandler) is a poor hockey player who still lives with his beloved Grandma. When he is forced to pay $270,000 to prevent his Grandmother’s house from being repossessed, he decides to apply his hockey skills to golf. He eventually meets Chubbs (a great Carl Weathers) a one-handed former pro golfer who becomes Happy’s mentor – helping him to channel his aggression into golf. Now only one man can stand between Happy and his quest to protect his mother’s house, the dastardly Shooter McGavin (Christopher McDonald).

Happy Gilmore was the follow-up to Billy Madison for Adam Sandler and basically improved upon everything that its predecessor set out. It had a better story, a better script, a better cast and definitely better jokes. As usual with most Adam Sandler films, the supporting cast are typically as funny as the man himself and Happy Gilmore is one of the finest examples of this. Carl Weathers is wonderful in a light-hearted role and his warmth in personality is easy to care for. However, Chris McDonald (who hasn’t done anything of massive note since) plays a fantastic foil to Sandler’s character, relaying off of Happy’s amateurish antics with the kind of snarky and snide personality that instantly makes you want to punch him in the face! Half the fun is seeing him not only give it to Happy but also when Happy gets his revenge ultimately. The “Happy Place Ruined” sequence is probably the best in the entire movie. Ben Stiller (in one of his earliest screen performances) and Richard Kiel (Jaws from the James Bond movies) also make neat little cameos too so watch out for when they pop up.

The success of Happy Gilmore and Billy Madison played a large part in establishing Sandler as a credible leading man for comedies. It had such a profound effect on his career that he decided to name his own production company, Happy Madison, after these two movies.

Best Sandman Moment: Happy’s Happy Place RUINED!

4. You Don’t Mess With The Zohan (2008)

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You Don’t Mess With The Zohan is as funny-as-hell if you’re the sort of person who enjoys good Adam Sandler movies. As a half-Arab myself, I have to admit that I went into this film a little bit anxious. Sandler is a well-reknowned Jewish actor, he’s playing a Mossad agent and he will be presenting the Israeli-Palestinian conflict in one of his comedy movies. Gulp! There was a massive risk here that he could deeply offend either one or both groups. Amazingly. He doesn’t. And it’s funny. Obviously, it was never going to be steeped in reality at all but the sentiment behind the movie is politically correct. Zohan is not here to bash Palestinians nor the Israelis at all – instead, the uselessness of fighting and also a man’s love for hummus (which I can totally understand). It could easily have turned into a “Arabs are terrorists let’s make fun of them” kind of movie and for the most part, Sandler manages to avoid this situation and also, more importantly so, keep it funny.

Zohan (Sandler) is a legendary super-human Israeli Counter-Terrorist agent who fakes his own death to avoid a tireless life of fighting a never-ending war. He resurfaces in New York where he can now pursue his real aspiration – as a hairdresser. He is astonished to find in his local neighbourhood that Jews and Muslims live in peacful co-existence. It is there however that he meets the stunning Dahlia (the very beautiful Emmanuelle Chriqui), an Arab hairdresser herself and begins to fall in love with her. However, when Palestinian operative Salim (Rob Schneider) spots him, it’s not long before his arch-nemesis The Phantom (John Turturro) makes another appearance to battle Zohan to the end.

I like Zohan a lot because it’s a rarity in the sense that it’s one of the few movies in existence that portrays Arabs as anything but backward terrorists. The number of times I have seen Saïd Taghmaoui play that character (and this is not a shot at him as an actor in any way because he is very talented) and every other generic Arab character in movies starts to get annoying after a while.

Putting personal feelings aside, this is still an off-the-wall hilarious movie that demands you do not take it seriously. Sandler is charming as Zohan who although has many reasons to be arrogant due to his apparent super-human capabilities, never is. Again, a great supporting cast including Turturro, Schneider and newcomer Daoud Heidami who are all very funny in their roles as the Arabs. There are many visual gags involving hummus, old ladies and funky dancing. Up to this point, there had been a section in Sandler’s career where he played the “straight man” continuously from Punch-Drunk Love in 2002 to 2007’s Chuck & Larry so it’s great to see that he still has these great and memorable characters he can portray.

Best Sandman Moment: The trailer sums it up very nicely…

3. Funny People (2009)

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The most recent addition to the Adam Sandler canon, Funny People marks his first on-screen collaboration with Judd Apatow – a man resonsible for many modern-day classics such as TV’s Freaks and Geeks, The 40 Year-Old Virgin and Knocked Up. What’s apparent in all of those works is that there is always a fine balance between outrageous comedy and very human drama – something that Adam Sandler is a master of.

Funny People tells the story of George Simmons (Sandler) – a depressed Hollywood actor and former stand-up comedian who is disillusioned with the emptyness of the riches in his life. Having learned that he is dying of a rare blood-disease, he decides to go back to his stand-up roots only to be heckled by up-and-comer Ira Wright (Seth Rogen). He decides that the best way to get back in touch with his former successes is to hire Ira as his personal assistant and gag-writer. George pines for Laura (Leslie Mann) who has moved on with a husband (Eric Bana) and two kids. Having learned that he may be free of his disease, he makes one last stand and reclaiming the former love of his life.

The two main stars of this movie are Sandler and Rogen – both with an equal amount of screen-time to display their comedic and dramatic talents in equal measure. What separates Funny People from most of Sandler’s other films, is that for probably the first time, he gets to play a complete character with both good points and bad points on display. George Simmons could easily be someone who lives in the real world and at times you wonder how closely is George modelled on Sandler’s own life if not on any other comedian-turned actor. Funny People is a movie that can be split in two – the first half being the comedy with a bit of drama and the second being the drama with a bit of comedy. What makes it work as a film is that the gut-wrenchingly funny moments make the heart-wrenching drama moments. The movie is effectively about living with regrets and whether as people we can change to prevent further mistake. This balance between chasing what you want and knowing when not to is very much encapsulated in Sandler’s terrific performance.

Best Sandman Moment: Just go see it while you still can… The great thing is, most of the jokes in the trailers are not even in the final movie!

2. The Wedding Singer (1998)

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If Happy Gilmore and Billy Madison made Adam Sandler a favourite with the guys, then there’s no doubt that The Wedding Singer made him a hit with the girls.

Set in the 80s, Sandler plays Robbie, a former rock star turned wedding singer who is down on his luck after being dumped by his long-time girlfriend on their wedding day. At the same time, Julia (the delightful Drew Barrymore) is preparing to marry her fiancée Glenn (Matthew Glace) and decides to hire Robbie to help set up the wedding. As time goes on, Robbie and Julia start growing on to one another and sparks fly. Robbie knows that Glenn is cheating on Julia and Julia feels guilty that she is having second thoughts about Glenn…

If you haven’t seen The Wedding Singer then stop reading this and go watch it now. Seriously. Turn the computer off and go. You can download the best of Jenna Jameson later.

For those of you left behind, you probably know exactly why this is so high on the list. It’s a GREAT movie, and because it’s set in the 80s it’s timeless too. There’s no doubt in my mind that 30 years from now it will be regarded as one of the classics from the 90s. It has a great story, fantastic soundtrack, sharp script but crucially, the chemistry of the leads in Sandler and Barrymore is both sweet and electric at the same time. What The Wedding Singer tends to conjure up in you are those first feelings of innocent love that you might have felt in your earlier years before you became a bitter, resentful and drug-using kleptomaniac (or is that just me?). Either way, I’m sure you’ll know what I mean when you watch this movie – that feeling of meeting someone that you can’t help but feel enamoured for and will stop at nothing to protect them. It’s a classic love story with a “pre-modern” day twist and was the first indication that Sandler had a softer side from most of his usual shouty, semi-retarded-type characters. It brought to people’s attentions that the Sandman could do rom-coms without losing his personal touch, as evident in his songs in the film “Somebody Kill Me” and “Grow Old With You”. Oh and he’s a talented singer-songwriter to boot with a great voice. Some guys have all the luck, eh?

It’s a sweet movie and to paraphrase Zach Braff describing his own movie Garden State (another favourite of mine)… “This is the kind of movie that you would take the girl you’ve always liked but been too afraid to ask out to in the cinema”.

Best Sandman Moment: Somebody Kill Me Please…

And here it is, the number 1 all time top Adam Sandler movie –

1. The Waterboy (1998)

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1998 was the year of Adam Sandler. Not only did The Wedding Singer drop but so did The Waterboy. Make no mistake about it, this was Vintage Sandler.

Bobby Boucher (Adam Sandler) is the waterboy for colleage football team, the Mississippi Mud Dogs as coached by Coach Klein (Henry Winkler). Bobby takes water aid seriously, much to the chagrin of his team which often leads to Bobby getting bullied by his teammates. Bobby’s Mama (Kathy Bates) loves him dearly, to the point that she passive-agressively prevents him from fully growing up into an independent man, which of course makes it difficult for Bobby to get the with school bad girl Vicky Vallencourt (the smoking hot Fairuza Balk). One day, the bullies push Bobby too hard and he snaps – unleashing a fury and anger that makes him a star in the team. Can Bobby gain his independence, win the adulation of the college and become his own man?

The Waterboy is number one for the simple reason that it’s classic Sandler. It’s perfect. From start to finish, it’s a laugh-a-minute movie that has me giggling every time I see it, no matter how many times I’ve seen it. The characters that he has portrayed throughout his film career, the Billy Madisons, the Happy Gilmores, the Little Nickys, the Zohans, etc are all great in themselves but have never been as perfectly executed as Bobby Boucher – The Waterboy. Sandler has created a memorable and original character that is both hysterical but also sympathetic as well.

The supporting cast is very, very good. Henry Winkler in definitely his best film role ever. Kathy Bates is unlike anything we’ve seen before – bloody funny. Fairuza Balk – oh my God, she was hot! What the hell happened to her?! Everyone else in this movie has at least one hilarious moment including all of Sandler’s crew – Rob Schneider, Peter Dante, Allen Covert, Jonathan Loughran but also Clint Howard, Blake Clark and freakin’ Lawrence Taylor!

Lots of standout quotes and one-liners, mostly from Sandler. It’s the movies where he’s playing a character instead of the straight man where he gets the most laughs and that’s what makes The Waterboy the ultimate Adam Sandler film.

The human elements are there too. As guys, we can all understand that plight from transforming from dependent boys who need their mommas into independent men who want to be the hero and to get the girl. But forget that, if you don’t find this film funny then you have no soul.


Best Sandman Moment: None. Why would I spoil the best film on this list? Go watch the movie – YOU CAN DO EET!

Airheads – doesn’t feature Sander enough but introduced him to Steve Buscemi.
Big Daddy – okay movie, Sandler forced Allen Covert and Peter Dante to do a gay kiss in order to give them their own movie, Grandma’s Boy.
Little Nicky – funny and dark movie, hurts not to put it in, slight overload with the supporting cast though – Harvey Keitel, Reese Witherspoon, Quentin Tarantino, Rhys Ifans.
Anger Management – because it showed Sandler could hang with a big name.
Mr. Deeds – but mostly for John Turturro being hysterical.
Click – for going places you don’t expect it to.

Also see: [News] New & Upcoming Adam Sandler Movies

Author Mahmoud is the creator of YouTube Sketch Comedy channel The Hard Comedy which you can visit & subscribe to here

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  • rude word said

    I just wonder… if you guys hate the guy so much, why are you on a website dedicated to him and his films??? is that how you spend your days? trawling the web for things you want to complain about??? dear me, if you dont like him, just dont watch him, simple as.

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  • connor maxass said

    duhhhhhhhhh………… adam sandler is the bommmmmmmb bbmmbmmbmmb bmmbmmbmmbmmbmmbmmbmmb

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  • jj said

    you forgot big daddy tho…

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  • adamsfilmguypissoffhaters said

    man adam sandler is the greatest but i would get rid of waterboy off the list and replace it with a better adam sandler like click but all his movies are awesome ALL IM collecting them and i have
    anger management
    dont mess with zohan
    big daddy
    the longest yard
    50 first dates
    funny people
    reign over me
    bedtime stories
    billy madison
    happy gilmore
    mr deeds

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  • Uriah said

    All good movies but you should include MR. Deeds

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  • UnicornsAss said

    I can’t stand Adam Sandler. I put him in the same boat as Jim Carrey.
    Both make faces and speak in idiot tones. Two of the worst actors ever. In fact, neither are even actors, they’re just morons on camera.

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  • MAB said

    billy madison, click, mr.deeds, waterboy, zohan are one of his best movies.

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  • puppy said

    ok, so. i LOVE LOVE LOVE adam sandler + his movies. i hate the 1 where he’s gay. anyway, i love the wedding singer, it rules. adam sandler is my hero! marry me adam. adam sandler is the best, chuck out the rest.:)

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  • puppy said

    in my world adam sandler is my husband along with a pomeranian dog, i’d love that life. he;d sing to me like in the wedding singer. p.s. i have EVERY adam sandler movie ever made at my place. I LOVE YOU, SANDLER

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  • puppy said

    every sandler movie rocks! i’d hate 2 be annoying but i’m only showing how much i love adam. s. ok. p.s. i am a pomeranian dog, its true. i want pet-pom-pal. ok, see ya’s soon i have to eat, sleep, play, chat and go 2 the toilet ok bye hunnys

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  • puppy said

    my favourite movie would have to be………….the wedding singer. it was #2 which means it rocked our world. adam sandler is soooooooooooooooooo sexy in the wedding singer. i like grown ups, too. adam is so funny i wet myself watching him say anything. yup. he rules, admit it.

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  • puppy said

    me and sandler says that dogs are better than cats! we have 1. adam has a bulldog called meatball and my name on this is the name of my dog, she’s a pomeranian. hey! adams dog should love my dog and i should love adam, simple. i’m a lovin girl. if u hate sandler i’ll X you. got it. i’m his wife, i wish.

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  • A1 said

    Not a bad top 10 but here is mine:

    10. Reign Over Me
    9. Click
    8. 50 first dates
    7. 8 Crazy Nights
    6. Mr Deeds
    5. Wedding Singer
    4. Billy Madison
    3. Waterboy
    2. Big Daddy
    1. Happy Gilmore

    Dam that was hard don’t hold me to this lol

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  • jayashree said

    u r too good in acting ADAM..i love watching your films

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  • Marisa said

    Realizing you made this list before Grown Ups, Big Daddy is my favourite movie from Adam Sandler and it would have been his highest grossing movie not The Longest Yard, so by that logic, it’s first : )

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