The 8 Best Adam Sandler Movies, Ranked

“The price is wrong, bitch!” – Happy Gilmore

From his early beginnings with SNL, Adam Sandler has become an A-List actor that often writes, produces, and stars in his comedy movies. And while the critics haven’t always been exactly receptive to Sandler over the course of his film career (spanning three decades), his ardent fans and box office returns say otherwise. And, with hits like Happy Gilmore, Billy Madison, and The Waterboy, the quotable lines are still as notable today as they were when they were first spoken on screen. He has acted alongside some of Hollywood’s greatest stars including Jack Nicholson, Kathy Bates, Dustin Hoffman, and Philip Seymour Hoffman, just to name a few. 

Something is bound to be wrong with your medulla oblongata if you don’t like a least a few of the films below.

Extra points if you can name at least 3 actors/actresses that often make a regular appearance in his films.

The Waterboy – 1998

When Bobby Boucher (Sandler) is fired as the waterboy from one football team, he becomes the waterboy for another team coached by Coach Klein (Henry Winkler). Bobby’s mother, Helen (Kathy Bates), is overprotective of her 31-year-old son and is constantly trying to shield him from the “evils” of the world. Bobby takes immense pride in providing the highest quality water for the team until he snaps due to teasing and it’s discovered that he has talent on the field (though he doesn’t completely relinquish his waterboy duties). He goes on to help the Mud Dogs have their first winning season.

Big Daddy – 1999

Some might argue this movie’s inclusion in the list. However, the quotable lines earn it a place in our ranking. Thirty-two-year-old bachelor, Sonny Koufax (Sandler) is a law school graduate but has chosen to instead work as a toll booth collector while avoiding any responsibility whatsoever. That is, until a five-year-old boy shows up on at his door and Sonny becomes an unlikely foster parent. 

50 First Dates – 2004

The first of two movies in this ranking that star Adam Sandler and Drew Barrymore (they have actually starred in three movies together). Henry Roth (Sandler) lives a charmed life in a Hawaiian paradise enjoying the company of endless vacationing women. That is, until he meets Lucy (Barrymore). However, Lucy was in a wreck years earlier and suffers from short term memory loss. With the end of each day, she forgets all of the previous day’s events. Therefore, Henry has to constantly look for new and inventive ways to make her fall in love with him all over again. 

Happy Gilmore – 1996

Happy (Sandler) is a wannabe hockey player who is constantly rejected. It’s discovered that his abilities are better suited to the gold course. He decides to try his hand at the game to raise enough money so that his grandmother can keep her house that was foreclosed on due to unpaid taxes. However, his unorthodox approach to the game will create havoc along the way. And, who can forget the fight scene between Happy and Bob Barker.

The Wedding Singer – 1998

This is our second on the list starring Drew Barrymore alongside Sandler. Set in 1985, Robbie Hart (Sandler) is a popular wedding singer entertaining guests with hits from the 1980s. When he is jilted at the altar on his wedding day, he is devastated. His friendship with Julia (Barrymore) begins to blossom as he helps her prepare for her weeding. As a bonus, Billy Idol makes an appearance as himself.

Reign Over Me – 2007

In contrast to the previous five movies in the ranking, this film looks at one man’s recovery from one of the most monumental events in United States history. This heartbreaking tale is about one man’s struggle to regain his life after a tragic loss. Charlie Fineman (Sandler) lost his entire family in the attacks on 9/11. By chance, Fineman reconnects with his college friend, Alan Johnson (Don Cheadle), who seeks to help him recover from his loss. In the end, Alan, who has become disenchanted with his own life, finds his road back to happiness as well. 

Funny People – 2009

Written and directed by Judd Apatow, Funny People explores the journey of stand-up comedian George Simmons (Sandler) after he discovers that he has a terminal illness. Simmons takes an aspiring young comedian, Ira Weiner (Seth Rogen), under his wing. Simmons eventually shares his prognosis with Weiner who ultimately convinces Simmons to share his plight with others including his ex-fiancée. Things don’t always go as planned. 

Punch Drunk Love – 2002

The only male among his eight siblings, Barry Egan (Sandler) is emotionally abused by his sisters. Egan owns his own company yet he leads a lonely life. He meets two women concurrently: One is a co-worker of his sister while the other is a phone sex operator who tries to extort money from him. The film is a rollercoaster ride as Egan navigates the troubled waters and new love. 

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