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Every Cameo From Adam Sandler Movies Ranked

Whether you love him or hate him, there is no denying that Adam Sandler has been one of the most influential and successful actors of recent times. The comedian's movies, often made under his own Happy Madison Productions banner, have grossed a total of more than $3 billion according to The Numbers — a figure that is all the more impressive given that most of his releases over the last seven years have been released exclusively on Netflix.

While Sandler's films have taken in many different genres and settings, there is one constant throughout all of them. The actor is certain to include a wide range of cameos in pretty much every movie he makes, often casting his friends in minor roles. It's something he has done throughout his career, from "Happy Gilmore" and "Billy Madison" all the way to "Hubie Halloween."

As you might expect, though, not all of these cameos are hits. There have been quite a few misses over the years and many of these brief appearances haven't landed with audiences. Let's go through every major cameo from Sandler's movies to see which ones were worth it and which ones should have been left out.

27. Rob Schneider

If there is one person that people associate with Adam Sandler films other than the actor himself, it would undoubtedly be Rob Schneider. A quick glance at Schneider's IMDb page reveals that he has appeared in more than a dozen Sandler films over the years, while also starring in his own Happy Madison Productions projects. Invariably he has played a comic sidekick of sorts, appearing in cameos where he would invariably motivate Sandler's characters by screaming "You can do it!"

Schneider ranks so low here not only because his cameos are usually painfully unfunny, but also because they are often actually offensive. As The Daily Beast notes, his cameos often involve him playing characters of various races. This has included playing a Latino character, a Middle Eastern character, an Hawaiian, and a Palestinian terrorist. Most of these roles have involved insensitive stereotypes that are simply not representative of the people they are supposedly mocking.

26. Tim Herlihy

The name Tim Herlihy might not be instantly recognizable to filmgoers but he has played an important part in Adam Sandler's career. As a writer on "Saturday Night Live," he provided sketches for many of the performers but struck up a relationship with Sandler. According to Entertainment Weekly, the two worked together on many of Sandler's earliest films, co-writing "Happy Gilmore" and "Billy Madison" while setting up a partnership that continues to this day. 

Herlihy went on to collaborate on the screenplays for "The Wedding Singer," "The Waterboy," "Mr. Deeds," "Big Daddy" and "Grown Ups 2" while also serving as an executive producer on several other Happy Madison Productions projects. While the two have not worked together as frequently in more recent times, Herlihy continues to have cameos in Sandler's movies, where he has played minor characters such as Bear in "Hubie Halloween" and Mr. O'Mally in "Sandy Wexler." None of these parts were particularly memorable or even that funny, suggesting that his talent was firmly in writing.

25. Dan Aykroyd

Unlike many others on this list, Dan Aykroyd has only had a single cameo in an Adam Sandler movie. He played the master of ceremonies for the championship tournament in "Pixels." The cameo was less than inspired and didn't come with any jokes. CinemaBlend suggests his appearance may have even had something to do with his Crystal Head Vodka, which is predominantly displayed later alongside a host of other obvious product placements.

Even if Aykroyd's performance in "Pixels" had been better, it would likely not have made his part any more memorable. After all, the film was widely panned by critics and fans alike, holding an approval rating of just 18% on review aggregator Rotten Tomatoes. In the end, it was just another example of the terrible video game movies that have been produced over the years — putting the "Ghostbusters" and "Blues Brothers" star's cameo low on this tally.

24. More than two dozen NBA stars

"Hustle" is Adam Sandler's latest movie for the streaming service Netflix. In the film, he plays an NBA scout called Stanley Sugerman who spends an inordinate amount of time on the road looking for fresh talent. Stumbling upon an unpolished yet clearly talented player while watching a pick-up game in Spain, he puts his career on the line to either get the recruit signed or into the NBA draft. Certified as fresh on Rotten Tomatoes, with an approval rating of 92%, it has been widely praised, with The New Yorker saying that Sandler "dominates" the film with his performance.

To help give the film a sense of authenticity and realism, there are a host of real-life basketball stars littered throughout the film. According to Vulture, these include Tyrese Maxey, Tobias Harris, Matisse Thybulle, Dirk Nowitzki, Julius Erving, Kyle Lowry, and Seth Curry. Coaches Doc Rivers, Dave Joerger and Dell Demps also appear, along with the likes of Brad Stevens and Mark Jackson. While none of these cameos are all that exciting or great on their own, they all contribute to making the world of "Hustle" feel genuine.

23. Jackie Sandler

Jackie Sandler may well look familiar to anyone who has seen an Adam Sandler film. She has some 38 IMDb acting credits to her name, with her first appearance coming in the 1999 movie "Big Daddy," where she played a waitress under the name Jacqueline Titone. Since then she has had minor roles in a wide array of Happy Madison Productions movies, including "50 First Dates," "Grown Ups," "Pixels," and "Sandy Wexler." However, Sandler has also appeared in other projects such as "Hotel Transylvania" and the 2022 movie "Deported."

Starting off as a model working for big fashion brands, she met her now-husband Adam Sandler on the set of "Big Daddy," according to People. The pair went on to marry in 2003 and have two daughters together. Her romance with the actor and comedian is likely the reason that she has appeared in so many of his films, but her performances are solid enough if not spectacular.

22. Peyton List

Peyton List is an actress and model who was born in 1998. Getting her break in the Disney Channel series "Jessie" in 2011, she went on to have lead roles in "The Thinning" and "The Thinning: New World Order" for YouTube Premium. More recently, she has appeared in "The Outcasts," "Valley Girl," and "Paper Spiders," as well as having a significant role in "Cobra Kai."

What some fans may not know, though, is that she also has a brief role in the 2020 comedy "Hubie Halloween." In the horror movie spoof, she plays Peggy, a haunted house employee who frightens Sandler's character thanks to her scary costume. Dressed as a ghost, she certainly has a striking appearance, but her on-screen time is so limited that many people won't even have realize who she is — especially when she is wearing so much makeup. That's the only reason it's not ranked higher among the cameos in Sandler's films.

21. Robert Smigel

Robert Smigel began his career as a writer on "Saturday Night Live" in the mid-1980s. He continued to write for the show and other series, going on to create Triumph the Insult Comic Dog on "Late Night with Conan O'Brien." Vanity Fair reports that this crass puppet continues to appear on "The Late Show with Stephen Colbert" to this day.

When it comes to working with Adam Sandler, Smigel has collaborated with the comedian several times. IMDb confirms he first appeared in "Billy Madison" and then in "Happy Gilmore," as the IRS agent that Happy throws through the door.

Smigel would go on to provide the voice for the dog Mr. Beefy in "Little Nicky" in what was perhaps his best performance, although it wasn't strictly a cameo. He's also shown up in other Sandler films and co-wrote "You Don't Mess with the Zohan" and "Hotel Transylvania 2."

20. Dennis Dugan

Despite not being a prolific actor, any avid fan of Adam Sandler's filmography will recognize Dennis Dugan's face. In the 1996 film "Happy Gilmore" he plays the commissioner of the Pro Golf Tour, the man responsible for deciding whether Happy can remain on the Tour. He clashes with both Happy and Shooter McGavin throughout the movie. His role in the movie was bigger than that, though, as he was also the director. This is a responsibility that Dugan also had on "Big Daddy," "I Now Pronounce You Chuck and Larry," "You Don't Mess with the Zohan," "Grown Ups" and others.

Before working as a director with Sandler, Dugan had appeared in a number of television series and films. Along with a recurring role in "Hill Street Blues," he also turned up on "M*A*S*H" and "The Rockford Files." Often appearing in his own movies, the director has cameos in several other Sandler releases, playing minor roles in "Big Daddy" and both "Grown Ups" films. Other than his "Happy Gilmore" performance, which was far bigger than simply a cameo, none have been important to the plot or particularly funny.

19. Melissa Villaseñor

Comedian, singer, painter, impressionist, and actor are just a few of the jobs that Melissa Villaseñor has had over the years. Best known for her work on "Saturday Night Live," where she has been a cast member since 2016, Villaseñor has also lent her talents to the likes of "Family Guy," "Adventure Time," and "Toy Story 4." 

In 2020, she had a brief cameo in "Hubie Halloween," playing a cat owner called Karen who's part of one of the funniest scenes in the movie. When Hubie saves her cat from certain death, Karen quickly begins to yell at him but Violent Valentine quickly jumps to his defense. Her threat to beat Karen with "her ugly cat" leads to shocked reactions from both Karen and the cat. The site of the aghast feline is more than enough justification for this cameo and ensures that Villaseñor is a memorable character with a standout scene in the movie.

18. Kevin James

Kevin James is a Hollywood star in his own right and has had a number of roles in Adam Sandler films along with other comedies. He starred alongside Sandler in "I Now Pronounce You Chuck and Larry" and then went on to lead his own film in the form of "Paul Blart: Mall Cop" and its sequel, before reteaming with Sandler for roles in "Grown Ups" and "Grown Ups 2."

Although James continues to be part of the main cast of recent Sandler films, he has also had a few cameos. The most notable was in "You Don't Mess with the Zohan," when he appeared as himself in an uncredited role. He earlier played a factory worker in "50 First Dates." The success of these roles ensured that James developed a strong relationship with Sandler and has been one of his closest collaborators in recent times, with the two sharing a strong bond that they both spoke about in an interview with WWE.

17. Colin Quinn

Like many of those who have had cameos in Adam Sandler's films, Colin Quinn has appeared in more than one movie. Those who have seen "Grown Ups" and its sequel will likely recognize him as Dickie Bailey. This character is a former childhood rival to Sandler's own Lenny and the animosity between them has continued into adulthood. While this confrontation, and later friendship, is one of the better aspects of the two movies, it is too large a part to be considered a cameo.

However, Quinn has had smaller roles in other Sandler movies after working with him for the first time in "Grown Ups." He played a janitor who has a habit of insulting the patrons of the museum where he works in "Hubie Halloween" and also had minor parts in both "That's My Boy" and "Sandy Wexler." Having parts that are actually funny is a big plus for Quinn, ensuring that his cameos are not just another famous face showing up for a few seconds without any purpose.

16. Courteney Cox

Although Adam Sandler has worked with another "Friends" star, Jennifer Aniston, in the likes of "Just Go with It" and "Murder Mystery," he has only shared a brief amount of screen time with Courteney Cox. The two appear together in the 2005 film "The Longest Yard" where she plays Lena. The uncredited character is the girlfriend of Sandler's Paul Crewe character and can be seen at the beginning of the movie. Sick of his behavior, she leaves him, but not before the former quarterback steals her car.

This is arguably one of the better cameos in a Sandler movie. Cox appears as a significant character who plays a major role right at the start of the story. The part isn't played for laughs or made silly, like many other Sandler-based cameos, and the performance is serious enough to get you to understand how far Crewe has fallen since being kicked out of the NFL.

15. Jonathan Loughran

Jonathan Loughran has been a regular fixture of Adam Sandler movies for decades now and his face will almost definitely be a familiar one to many members of the audience. According to the Philadelphia Inquirer, Loughran was working at the Improv comedy club in Los Angeles when he became friends with Allen Covert, who then went on to introduce him to Sandler. The two got on like a house on fire and Loughran soon began working as Sandler's personal assistant. One perk of this was that Sandler has cast him in almost every single one of his movies since.

Thanks to his ability to make himself cross-eyed at will, the actor has carved something of a niche role for himself in Hollywood. In many of his cameos in Sandler films, he uses his cross-eyed skill to comedic effect, portraying funny and unique characters. Although his parts aren't necessarily the most important, they all add something positive and humorous to the overall experience.

14. Blake Clark

Blake Clark is probably best known as a stand-up comedian rather than an actor, but he has still appeared in a number of films over the years — the vast majority of them being Adam Sandler movies. According to IMDb, he has appeared in some 12 Happy Madison Production projects, including "Little Nicky," "Mr. Deeds," "Grown Ups," and "I Now Pronounce You Chuck and Larry." Almost all of these appearances have been small cameos, with Clark playing a humorous character who can fit into several different molds to suit the movie in question.

Perhaps his most famous cameo is in "The Waterboy," where he plays Farmer Fran. He is the assistant coach to Henry Winkler's Coach Klein. A proud local, he seemingly speaks nonsense and helps show just how far the Louisiana Mud Dogs have fallen by having a person like this as part of the staff. In that sense, he plays an integral role, making this cameo an important piece of the movie.

13. Tim Meadows

Actor and comedian Tim Meadows is probably best known for his stints on "Saturday Night Live" along with the sitcoms "Schooled" and "The Goldbergs." He has also frequently appeared in Adam Sandler movies in cameo roles over the years. Most of the time, these minor parts are not all that important to the plot and he often doesn't have all that much screen time. Since 2010, he has appeared in "Grown Ups" and its sequel, "Grown Ups 2," along with "Jack and Jill" and "Hubie Halloween."

Although he has some funny lines in the two "Grown Ups" movies, it is "Hubie Halloween" where Meadows shines the most. Sharing a scene with Maya Rudolph, he's part of a bickering married couple who share a love for messing around with Hubie. The interactions between them are some of the most hilarious moments in the film and stand out among the many cameos in "Hubie Halloween."

12. Dan Patrick

Although he isn't known for his movie appearances, and works primarily as a sportscaster and radio personality, Dan Patrick nevertheless has had roles in some 35 films. Many of these have been in Adam Sandler projects, as you might imagine, with his first Happy Madison production being "The Waterboy" in 1998. Since then, he has had roles in more than 10 Sandler movies, ranging from "The Longest Yard," where he played a police officer, to "Grown Ups," in which he showed up as Norby the Ride Guy.

His most recent roles were as a school principal in "Hubie Halloween" and a cameo in "Hustle" playing himself. Despite not being an actor by trade, Patrick has a sense of comedy and can definitely deliver a funny line when needed. His cameos have usually been some of the better ones in Sandler movies, not relying on catchphrases or silly antics to get laughs. That, at least, makes his appearances feel worthwhile.

11. Chris Farley

Chris Farley was something of a titan of comedy before his untimely passing in 1997. His film career had only really started to hit its stride when he died, so it means that he didn't appear in all that many films. One of these was an uncredited role in "Billy Madison" as the school bus driver, according to IMDb. A recurring part in the film, his performance is genuinely one of the funniest elements of the entire movie.

The bus driver himself is a creepy and somewhat perverted character who has a thing for Veronica Vaughn (Bridgette Wilson). He often talks to Billy about what he would like to do to the school teacher and also has a strong dislike for the children he has to transport around the city. TV Guide pointed out that the bus driver was a highlight of the film, adding that it might have benefited from more absurd elements such as his cringe-inducing character.

10. Billy Idol

"The Wedding Singer" might well be Sandler's greatest comedy film. Sandler stars as the title character, a performer named Robbie Hart who is attempting to win the heart of a waitress named Julia Sullivan (Drew Barrymore) as both of their other relationships fall apart. Featuring the additional talent of Christine Taylor, Allen Covert, and Angela Featherstone, the movie is a heartfelt but also hilarious story.

Near the end of "The Wedding Singer," Billy Idol appears on an airplane among a group of passengers who listen to Robbie's story about his pursuit of and love for Julia. Idol then helps to convince Sandler's character that he needs to win her back and even helps him perform a song that Robbie has written. When his rival Glenn tries to stop him, Idol and the flight attendants block Glenn's efforts. The extended cameo is a highlight in what is already a great film and Idol's wry smirk adds some extra humor to a few dirty jokes.

9. Ozzy Osbourne

Ozzy Osbourne has not appeared in all that many films, but the famous heavy metal singer and Black Sabbath frontman did have a significant role to play in "Little Nicky." Sandler's sixth major movie sees one of the sons of Satan, called Nicky, attempting to rescue his father and put a stop to his brother's schemes. According to Box Office Prophets, the film was a financial disaster, bringing in just $58 million against a budget of $80 million.

"Little Nicky" contains a large number of cameos, even by the standards of Sandler's movies. Its IMDb page lists almost 40 cast members, among them many regulars that fans would expect to see. However, Osbourne's appearance might have been a surprise to many. Playing on an unfortunate incident recently retold by Rolling Stone, where he bit the head off a live bat on stage, he appears at a decisive battle and attacks Nicky's brother Adrian when he is in bat form. Not only is this a hilarious callback to an important moment in rock history, but an important contribution to the story.

8. Carl Weathers

One of the stars of the "Rocky" films, Carl Weathers is no stranger to appearing in Hollywood movies. His first collaboration with Adam Sandler came in 1996 when he played Chubbs Peterson in "Happy Gilmore." The character acts as the golf coach and mentor to Sandler's character, helping to guide him to win the Tour Championship and win back his grandmother's house. It was a striking change in tone for the actor who was famous for his action roles but won praise from fans, as evidenced by these IMDb user reviews.

"Happy Gilmore" was not the final appearance of Chubbs Peterson. Weathers reprised the role in the 2000 film "Little NIcky" for a brief scene. Appearing alongside Reese Witherspoon, he is part of a welcome party that ushers Nicky into heaven. Not only is it a nice callback to his previous role, but the cameo actually makes some sense, as Chubbs died in "Happy Gilmore" and could well have made his way to heaven.

7. Lee Trevino

Lee Trevino is a former professional golfer who is widely respected in the game and was described by Sports Illustrated as "one of golf's most memorable and enduring figures." As well as being a successful player, Trevino was also known for his sense of humor on and off the course. ESPN even reported that the golfer was known as Merry Mex, in reference to his antics and his Mexican ancestry, and was no stranger to providing witty one-liners to the press or to his fellow professionals.

In that respect, it makes sense that Trevino would make a cameo appearance in "Happy Gilmore." His sense of humor and connection to the sport make him a perfect choice. His cameo consists of Trevino playing himself and shaking his head disapprovingly at Happy's behavior at various points throughout the movie. His cameo was a welcome addition to the film even if the golfer did regret his appearance.

6. Ben Stiller

Ben Stiller has made two cameo appearances in Adam Sandler movies throughout his career. The first was far more involved, with the actor playing Hal L., an evil orderly at a nursing home who forces the residents to provide free manual labor in "Happy Gilmore." He mistreats all of those staying at the facility, although acts as if he is a gentle and friendly employee whenever Happy is around. Stiller's character is so sadistic that other residents are seen trying to escape to avoid being punished.

With Stiller not appearing in any further Sandler movies in the intervening two decades, many might have assumed they had seen the last of him — until he made a brief appearance in "Hubie Halloween." The actor reprised his role, once again playing Hal in the opening scene of the horror spoof. His original role added some jeopardy to "Happy Gilmore," as it made getting Grandma's house back even more important, while his second appearance was a satisfying reference to the earlier movie.

5. Henry Winkler

Henry Winkler, known for his role as Arthur "Fonzie" Fonzarelli on the sitcom "Happy Days," first appeared in an Adam Sandler movie back in 1998 with "The Waterboy." This role, however, was not a cameo but a major part. He played Coach Klein, who was in charge of the Mud Dogs. Although he helps Sandler's Bobby character gain some confidence and is an inherently good person, he suffers from a mental block that stops him from developing new plays for the football team.

After this, Winkler went on to appear in a variety of Happy Madison Productions films. He had another important part in "Click, " playing the father of the main character. The actor also made cameo appearances in "Little Nicky," "You Don't Mess with the Zohan," and "Sandy Wexler." These cameos involved Winkler playing himself and showing his comedic chops, even in movies that were less than stellar. Any scene involving the veteran star — whose other credits include "Scream" and "Arrested Development" — was sure to at least have a few laughs in it.

4. Shaquille O'Neal

Shaquille O'Neal needs no introduction, as one of the most famous basketball stars of all time. Since retiring from the sport, O'Neal has worked as a sports analyst for "Inside the NBA" and is regarded by many to be one of the greatest athletes to play the sport, according to Bleacher Report.

Over the years, the former center has appeared in a number of movies, going back to his debut in the 1994 basketball drama "Blue Chips." His first appearance in an Adam Sandler film came in 2011, with a cameo in "Jack and Jill," which he followed up with a more significant role in "Grown Ups 2" as Officer Fluzoo.

More recently, he appeared in "Hubie Halloween" briefly as DJ Aurora. Throughout the film, the radio personality narrates the action in a soothing voice. At the conclusion of the action, it becomes clear that the DJ is none other than O'Neal. It's a funny reveal and an unexpected twist that gives the ending of "Hubie Halloween" an interesting extra element.

3. John McEnroe

John McEnroe was not only a brilliant tennis player but was also known for his confrontational behavior. This made him a popular figure among fans but caused issues with tennis authorities. So it was perhaps surprising that he made a transition to television and movies after his sporting career ended. While the vast majority of this has been involved in sports analysis for US and UK broadcasters, he has also appeared in a variety of entertainment projects.

Some of his most well-known movie roles have come in — you guessed it — Happy Madison films. His first, and most successful, was in "Mr. Deeds" in 2002. He played a fictional version of himself who gets drunk with Sandler's character and becomes involved in a series of controversial events. These scenes are among the very best in the movie and one of the parts that people remember the most. McEnroe would later appear in both "You Don't Mess with the Zohan" and "Jack and Jill," playing very similar roles.

2. Steve Buscemi

Although he is a respected actor who has had roles in films such as "Reservoir Dogs," "Armageddon," "Fargo," and "The Death of Stalin," Steve Buscemi has also developed a relationship with Adam Sandler. He has appeared in many Happy Madison Productions movies, ranging from "Big Daddy" to "Hubie Halloween, making a total of almost a dozen cameos in Sandler's filmography.

In these films, he often plays crazed or eccentric characters for comedic effect, creating absurd situations. It's a niche that has made him a valuable addition to many of Sandler's films and is always one of the highlights, largely thanks to Buscemi's considerable acting abilities. His favorite role was in "Billy Madison," where he played a deranged former student who eventually saves Billy near the end of the film. In addition to his work with Sandler and his other big screen roles, Buscemi's extensive TV resume includes the lead in the acclaimed crime drama "Boardwalk Empire," as well as guest stints on "The Sopranos" and "30 Rock."

1. Bob Barker

Without a doubt, the best cameo in any Adam Sandler film was from the legendary Bob Barker, known for hosting "The Price Is Right" for 35 years between 1972 and 2007. While he was a regular on other television shows and has made some cameo appearances in the likes of "SpongeBob SquarePants," his movie career was largely limited to the Adam Sandler film "Happy Gilmore." In the 1996 film, Barker plays himself and is teamed up with Happy in a Pro-Am golf tournament with disastrous consequences.

With Happy failing to impress the game show host, the two soon begin arguing and they get into a fight. The confrontation was named Best Fight on the MTV Movie Awards. One of the best scenes in "Happy Gilmore," it has become a fan favorite and even led to a second round in 2015 as part of "Night of Too Many Stars: America Comes Together for Autism Programs" on Comedy Central. Directed by Tyler Spindel, the sequel battle sees Sandler and Barker throw down once again in a hospital.