Adam Sandler: the best and worst in comedy
- mwoldridge02
- Jul 9
- 5 min read
Published by Mason Oldridge, 9 July 2025
CONTAINS SPOILERS!
Adam Sandler is one of the most popular and successful comedy actors in the movie industry, and while he has been at the helm of much comedy gold, he has also had his fair share of some golden raspberries too. This summer is set to see one of his greatest hits get its long-awaited sequel nearly 30 years on, so grab a tub of popcorn and a glass of high quality H2O as we take a look back at three decades of both his highs and his lows!

We start back in the 90s with a hat-trick of classics. First up is Billy Madison (1995) in which Sandler plays the titular character, a manchild who must go back to school to prove his worth in order to inherit his successful father’s company, an enjoyable watch on the whole. Happy Gilmore (1996) sees Sandler play the titular character again, this time an avid hockey fan whose anger issues lead him to professional golf instead and he enters a competition to raise funds for his grandmother’s house. His short fuse provides much of the comedy and the film contains a strong supporting cast too as Carl Weathers plays Chubbs, Gilmore’s one-armed (following an alligator attack) former pro mentor and Ben Stiller is hilarious as Hal L, the abusive carer at the retirement home. The sequel coming this summer will see Happy come out of retirement to fund his daughter’s ballet school. Another sports comedy rounds off the trio: 1998 film The Waterboy. Bobby Boucher is a mentally challenged adult waterboy for a university football team, who becomes one of their star players. The film has gone on to develop a cult following.
Earlier in the year, The Wedding Singer, the first of three romcoms co-starring Drew Barrymore, was released. Set in the 80s, it tells of a wedding singer and a waitress who fall in love. The comedic highlight is Julia’s unfortunate would-be married name, while the romance makes it a well-rounded wholehearted movie. In 1999, Big Daddy was released, in which a slacker begins parenting a five-year-old to prove his responsibility to his ex-girlfriend. The chemistry between Sandler and the Sprouse brothers, who would go on to play Zack & Cody, and the mischief they get up to makes for a fun watch. Little Nicky was released in 2000 and Sandler’s first flop. It sees him play the youngest son of Satan who must return his brothers to Hell when they rebelliously possess people in New York. A fantasy-comedy starring a possessed talking bulldog, the ridiculousness of the film leaves it as a mess.
In 2002, Sandler received praise as the lead in Paul Thomas Anderson’s Punch-Drunk Love. That same year, he starred in Mr. Deeds, a remake of the 1936 film by Frank Capra. It sees a small-town pizzeria worker learn that he is the heir of a billionaire and whisked off to New York City. Despite a negative reception, the film excels thanks to the comedy of butler Emilio, the romance between Deeds x Babe and the enchanting locations, making it one of Sandler’s best entries that flies under the radar. He then co-starred alongside Jack Nicholson in the 2003 comedy Anger Management. In 2004, he reunited with Drew Barrymore for their second romcom 50 First Dates, this time starring Sandler as a veterinarian who falls for an art teacher with amnesia, and attempts to impress her all over again every day. Later that same year, Sandler starred in another romance film, this more the more drama-orientated Spanglish. It follows Mexican immigrants in America working for a chef (Sandler’s character). The film is incredibly stale and drab, essentially a whole lotta nothing, another to join the disappointment list.
2005 and Sandler is back with another sports comedy The Longest Yard, a remake of the 1974 original in which a football player goes to prison. You better like sports films for this one as it’s otherwise unenjoyable. In 2006 came one of his biggest successes Click, in which he plays a husband and father who has a remote that can control reality. Christopher Walken is a great choice as Morty, the Angel of Death, the moral about cherishing time with family is a good one and the scene in which a broken Michael is dying outside the hospital is surprisingly heartbreaking, showcasing his talent outside of comedy. Sandler co-stars with Kevin James in 2007’s I Now Pronounce You Chuck & Larry as they play two firemen who pretend to be gay for life insurance. The film has some good laughs, though attracted much controversy for its homosexual stereotypes (as well as use of yellowface) and simply wouldn’t be made today. You Don’t Mess with the Zohan (2008) sees Sandler in a vastly unconventional role for him as an Israeli soldier who fakes his death to realise his dream of becoming a hairstylist in New York. Zohan’s Scrappy Coco alias and superhuman powers make him a hilarious character and the film can be praised for its daring detailing of the Israeli-Palestinian conflict. Later that year, he starred in Disney’s Bedtime Stories as a hotel handyman whose tales he tells to his niece and nephew come true in what is a more enchanting offering with Sandler.
In 2010, Grown Ups was released, starring Sandler alongside regular collaborators Kevin James, Chris Rock, David Spade and Rob Schneider as a group of childhood friends who reunite for a weekend away. They find their childish antics don’t quite play out the same as adults with families and responsibilities and, while the film isn’t great, it is still a fun watch, with its box office success spawning a sequel. He then starred with Jennifer Aniston in 2011 romcom Just Go With It, as a plastic surgeon who convinces his colleague to pretend to be his separated wife so he can seduce a younger woman. Nick Swardson, who usually has a minor role in Sandler productions, delivers the funniest moments as a fake German sheep seller, and the whole ruse sees the leads fall in love. Later that year, in Jack & Jill, Sandler appears as Jack and his twin sister Jill in a cliché that is as bad as it sounds. Then in 2012’s That’s My Boy, he plays the alcoholic father of Andy Samberg’s character in what was another flop.
2014’s Blended marked the third romcom with Sandler and Barrymore, this time starring as single parents who are forced to holiday together after an unsuccessful blind date, with them and their children forming the titular family dynamic. The format works really well, particularly as they help each others’ children of the opposite sex. Later that year, he starred in The Cobbler as the titular character who can assume the identity of his customers. Despite being generally panned, the story is original and delights in its magic realism. In 2015 came Pixels, in which a group of arcade champions are enlisted to help defend Earth against an alien invasion using classic characters. Nostalgia heavy, the film pays homage to classic 80s video games and serves as an epic sci-fi movie.
Pixels would be Sandler’s last film before signing an exclusive deal to move to Netflix, which marked a significant downgrade in quality. Starting with The Ridiculous 6 in 2015, a terrible attempt at a Western-themed comedy, a trail of poor productions followed; notably, 2017’s Sandy Wexler is one of the worst films of all time. The few exceptions are The Meyerowitz Stories (New and Selected) (2017) and Uncut Gems (2019) in which he earned praise for his dramatic performances and 2020’s Hubie Halloween, in which he returns to his classic local idiot role and is the optimum movie for the spooky season.
Despite the recent string of flops, there is still hope as Sandler’s next leading film is the sequel to one of his best and most successful comedies Happy Gilmore, though only time will tell if it lives up to its predecessor three decades prior. Despite being a tale of two sides, Sandler’s hits overshadow the shits to cement him as a comedy great.