Adam Sandler rose from a standup comic to one of the world’s biggest Hollywood stars in the mid 90s. Along the way, he has brought many of his friends along for the ride. While many of his rat pack of comedians were very much on their own path to success, there’s no denying that Sandler’s fame elevated them to new heights as his name ascended.
Across his storied career, Sandler has become iconic for wrangling together star-studded lineups for his movies. With the majority of his films produced by his own company Happy Madison Productions, he has often had free rein over who he shares the screen with. To that, the same names pop up again and again. So, here are the actors Adam Sandler has worked with most frequently, creating his very own rat pack of comedy.
Henry Winkler
Henry Winkler first collaborated with Adam Sandler in the zany hit comedy movie, The Waterboy. By this point, he was already a huge name in Hollywood after portraying the iconic Fonzie in Happy Days. In The Waterboy, Winkler brought his star power to the movie as Coach Klein, a stern football coach who begrudgingly takes Bobby Boucher (Sandler) under his wing when he reveals himself to be much more than a water boy after brutally tackling another player. Since The Waterboy, Winkler has starred in an array of Sandler’s movies, often playing a father figure of sorts. In fact, in the 2006 movie Click, Winkler took on the role of Sandler’s character’s father. He also starred in You Don’t Mess with the Zohan (2008), Little Nicky (2000), and Sandy Wexler (2017).
Chris Rock
Adam Sandler and Chris Rock first crossed paths in their teenage years when they were both moving up in the comedy world. However, they wouldn’t share the screen together until the 2005 movie The Longest Yard. The movie was a great success for MTV Films, serving as their highest-grossing film at the time of its release. Amongst the star-studded line up, Rock and Sandler’s chemistry was one of the most magnetic factors, as their real-life friendship added a layer of authenticity towards their banter. Since The Longest Yard, Rock has appeared in five more of Sandler’s movies, often in supporting roles or even cameos. Yet, in The Week-Of, the dynamic duo shared leading roles as two fathers with opposing personalities who must come together for their children’s wedding.
Kevin James
Kevin James joined Adam Sandler’s comedy rat pack a little later than the others, first starring in 2007’s I Now Pronounce You Chuck & Larry. The film centers on a widow and his boisterous friend who marry each other in order to receive domestic partner benefits. James starred as the straight-laced of the duo, while Sandler played an eccentric ladies man with a penchant for mischief. This movie kickstarted a string of movies for Sandler and James with Grown Ups following in 2010, and Grown Ups 2 in 2013. James has also shared the screen with Sandler in Pixels, Hubie Halloween, and Sandy Wexler. Additionally, Sandler made a memorable guest spot on Kevin James’ hit TV series The King of Queens, playing an old school mate of Doug (Kevin James), who goes crazy at a reunion.
David Spade
David Spade has starred in an array of Adam Sandler’s films, starting with Coneheads, which was one Sandler’s first major movie roles. Spade’s parts have often been small in Sandler’s movies, however, he shared top billing in the 2016 action-comedy, The Do-Over. Spade has also starred in Happy Madison productions like Joe Dirt, and The Wrong Missy.
Rob Schneider
Rob Schneider is another member of Adam Sandler’s comedy rat pack who often stars in smaller roles. However, although his parts are in the supporting realm, they are usually standouts due to their sheer wackiness, such as his rendition of Nazo in Big Daddy, a takeout delivery driver who is awful at his job but a kind friend to Sonny (Sandler). Schneider has also shared the screen with Sandler in movies like The Waterboy, Little Nicky, Mr. Deeds, Bedtime Stories, Grown Ups, 50 First Dates, and The Ridiculous 6. Outside of these supporting roles, Schneider has shined as a leading man in the Happy Madison repertoir. In 1999, he led the cast of the first ever Happy Madison movie, Deuce Bigalow: Male Gigolo. He then stayed at the forefront in movies like The Animal, The Benchwarmers, and The Hot Chick.
Nick Swardson
Much like Kevin James, Nick Swardson joined Adam Sandler’s comedy rat pack in the 2000s, given that he is the younger of the bunch. He first shared the screen with him in a small role as a Bed Bath & Beyond salesman in Click. However, prior to this, he co-wrote and starred in the cult comedy hit Grandma’s Boy, which was produced by Happy Madison Productions. From here, he has become a righthand man to Sandler, starring in a total of 13 Adam Sandler movies. In June 2024, Swardson confirmed via Instagram that he will be joining the cast of the highly-anticipated Happy Gilmore 2, which is currently in pre-production.
Steve Buscemi
Steve Buscemi is perhaps the most decorated actor in Adam Sandler’s comedy rat pack. He is renowned for working with some of the most prestigious filmmakers of all time – including Joel and Ethan Coen, Quentin Tarantino, and Robert Rodriguez. His breakout performance came from 1992’s Reservoir Dogs, playing a ruthless criminal. He then went on to star in cult classics like Fargo, The Big Lebowski, and blockbusters like Armageddon. However, he has never become snobbish when choosing his roles, often taking small and wacky parts in Sandler’s movies. The two first struck up a bond when they starred in Airheads together. After this, Buscemi has featured in 11 Adam Sandler movies and lent his voice to all three Hotel Transylvania films.
Peter Dante
Peter Dante is a member of Adam Sandler’s comedy rat pack who has shared the screen with the comedy titan a total of 11 times. He also starred in many other Happy Madison films such as Strange Wilderness, Grandma’s Boy, and Bucky Larson: Born to Be a Star. The comedian has never really worked his way up to leading man, mostly starring in cameo roles. Dante hasn’t worked with Sandler since Grown Ups 2 in 2013, with many speculating that Sandler has distanced himself from him after he faced allegations of violent threats and racial slurs.
Allen Covert
Allen Covert first teamed up with Adam Sandler in Going Overboard in 1989. This was both Sandler’s and Covert’s movie debut, and since then, they have become good friends and frequent collaborators. As of writing, Covert has shared the silver screen with Sandler in 21 pictures. He also co-wrote the screenplay for Grandma’s Boy with Nick Swardson, as well as taking on the lead role. Want to read more about Adam Sandler’s career? Here are all of his dramatic movie roles, ranked from worst to best.
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