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.

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.

"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.

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.

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.

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.

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.

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.

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.

"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.

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.

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.

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.

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."