Beyond the Big Laughs: Unearthing the Legacies of Adam Sandler’s Deceased Co-Stars

Love him or hate him, there’s no denying that Adam Sandler has carved out an indelible mark on Hollywood. Since the 1990s, this former “Saturday Night Live” standout has delighted audiences with a veritable profusion of comedy movies—some undoubtedly great, others perhaps not so much—that have consistently sparked laughter, and occasionally, a few groans, from viewers worldwide. Throughout his extensive career, Sandler has not only established a core team of dependable comic friends like Chris Rock, Kevin James, David Spade, and Rob Schneider, but he has also collaborated with some of the biggest names in the industry, including Jennifer Aniston, Steve Buscemi, and, of course, Drew Barrymore. He is, if nothing else, a truly skilled collaborator who brings out the best in his ensemble casts.

Over the decades, Sandler’s flicks have been graced by a diverse slew of talented cast members, featuring everyone from NBA stars to musical icons, all contributing memorable performances in supporting roles. Some of these incredible talents were one-offs, appearing in just a single film, while others returned for more on-set laughs across multiple projects. Given that the Sandman has been actively making movies for well over two decades, it’s an unfortunate and inevitable reality that some of these cherished former costars are, sadly, no longer with us. Their passing leaves a void, but their cinematic contributions, especially alongside Sandler, continue to entertain and inspire new generations of fans.

Join us as we take a heartfelt journey through the careers of some beloved actors from Adam Sandler’s movies, stars whose passing you might not have known about. Each brought their unique spark to the screen, creating moments of humor, pathos, and unforgettable charm that are deeply woven into the fabric of Sandler’s cinematic universe. We’ll explore their lives, their most memorable roles, and the enduring impact they’ve left on both their colleagues and their adoring public, keeping their spirits alive through the magic of film.

1. **Richard Kiel**

When you think of towering figures in cinema, Richard Kiel immediately springs to mind, almost certainly most recognized for his iconic portrayal of the notorious steel-toothed Bond villain, Jaws. He struck fear and awe into audiences in both 1977’s “The Spy Who Loved Me” and 1979’s “Moonraker.” However, before his passing, Kiel also made a truly unforgettable appearance alongside Adam Sandler in the beloved comedy “Happy Gilmore,” proving his versatility extended far beyond villainy and into the realm of comedic genius.

In “Happy Gilmore,” Kiel’s immense physical presence, standing at an impressive 7 feet, 2 inches tall, was perfectly utilized to create an intimidating figure in the gallery at Gilmore’s golf tournaments. Yet, despite his imposing stature, he consistently found himself in hilariously awkward and often antagonistic situations with Gilmore’s smug rival, Shooter McGavin, played by Christopher McDonald. His deadpan reactions and silent menacing glares added a unique layer of humor to the film, making his character, Mr. Larson, an unexpected fan favorite who always crossed paths with Shooter McGavin in the most amusing ways.

Beyond the screen, it appears a genuine camaraderie blossomed between Kiel and Sandler on set. When Richard Kiel passed away in September 2014, Adam Sandler publicly mourned the loss of his friend on X (then known as Twitter), sharing a heartfelt tribute: “Richard Kiel was one of the nicest, funniest guys I’ve ever met. I’ll never forget hanging out with him and how good he was to everyone.” This sentiment speaks volumes about the man behind the formidable characters.

It is widely believed that the towering actor died of a heart attack, though his death certificate also indicated he suffered from coronary artery disease, contributing to his ultimate demise. Regardless of the specific medical details, Kiel’s legacy as one of Hollywood’s truly greatest giants, celebrated for both his intimidating presence and his surprising comedic timing, is undeniably cemented. His work in “Happy Gilmore” remains a testament to his ability to steal scenes with minimal dialogue but maximum impact.

2. **Ray Liotta**

The world was truly rocked by the news of Ray Liotta’s death in May 2022. A mega-talented actor, he was perhaps best known for his gripping portrayal of the main protagonist, Henry Hill, in Martin Scorsese’s seminal 1990 gangster classic, “Goodfellas.” Liotta passed away peacefully in his sleep while diligently working on the upcoming movie “Dangerous Waters” in the Dominican Republic, leaving behind an incredible body of work at the age of 67.

Throughout his distinguished career, Liotta amassed a slew of movie credits and garnered impressive awards, including a well-deserved Emmy win for outstanding guest actor in a drama series for his powerful work in “ER.” While his passing is, by now, relatively common knowledge among film enthusiasts, it might come as a surprise to some that this esteemed actor also starred in one of Adam Sandler’s Netflix movies before his death, showcasing his willingness to explore diverse roles and collaborate with various comedic talents.

In 2020’s “Hubie Halloween,” the “Shades of Blue” actor took on the role of Pete Landolfa, one of Hubie’s many bullies. Although Liotta’s character in the film was undeniably a major jerk, Adam Sandler was quick to emphasize that the actor was the polar opposite in real life. Sandler tweeted a touching tribute, describing Liotta as a “tremendous actor” and a “sweetheart of a dad,” further adding, “[He was] such a great funny man to know. Prayers are with his whole family.” This heartfelt message painted a picture of a man beloved by his peers, despite the tough guy characters he often embodied onscreen.

Liotta’s ability to transition from intensely dramatic roles to comedic ones, even if his “Hubie Halloween” character was an antagonistic one, demonstrated his remarkable range. His passing left a significant void in Hollywood, but his powerful performances, from the streets of “Goodfellas” to the quirky town of “Hubie Halloween,” ensure his memory and talent will continue to be celebrated by audiences for years to come. His willingness to dive into any role, no matter how small or seemingly out of character, made him a truly unique and respected artist.

3. **Alexis Arquette**

One could reasonably argue that some of Adam Sandler’s most cherished works are his delightful romantic comedies, particularly those he shared with the incredibly talented Drew Barrymore. The two stars possess a magical chemistry that truly brings out the best in each other, and their three collaborative films—1998’s “The Wedding Singer,” 2004’s “50 First Dates,” and 2014’s “Blended”—are all, quite honestly, phenomenal movies that are both heartwarming and genuinely hilarious. Interestingly, there was almost always another memorable presence who tagged along whenever Barrymore and Sandler teamed up: Alexis Arquette.

Arquette was a truly talented character actor, celebrated for her distinctive portrayals, and also a passionate transgender activist who courageously transitioned into a woman in 2004, living her truth openly and inspiring countless others. Sadly, she passed away in late 2016 after suffering a heart attack, a tragic event that occurred while she was also courageously battling AIDS. Her untimely passing was a profound loss to both the acting community and the LGBTQ+ advocacy space, where her voice was vital and her presence powerful.

In a moving statement released after her death, her siblings—Patricia, Rosanna, Richmond, and David Arquette—praised her unwavering commitment to living authentically, as reported by The Guardian: “Despite the fact that there are few parts for trans actors, she refused to play roles that were demeaning or stereotypical… She was a vanguard in the fight for understanding and acceptance for all trans people.” This powerful testament highlighted her integrity and her significant role in advancing trans rights and visibility in an industry often resistant to change.

Alexis Arquette’s final appearance in a feature film before her passing was in 2014’s “Blended,” where she had a brief but memorable cameo as Georgina/George Stitzer. This was the very same character she had brilliantly played in 1998’s “The Wedding Singer.” In both movies, she delivered an uncanny and captivating performance as a Boy George impersonator, doing it so remarkably well that the iconic musician himself, Boy George, tweeted his sorrow upon learning of her passing, noting she was “another bright light gone out far too soon.” Her ability to inhabit such a unique character with grace and humor left a lasting impression, cementing her place in Sandler’s comedic legacy and beyond.

4. **Cameron Boyce**

While the pain of losing anyone is profound, there is arguably nothing quite as heartbreaking as losing someone who still had an entire lifetime of potential stretched out before them. This is precisely the tragic reality in the case of Disney Channel breakout star Cameron Boyce, who in 2019, at the incredibly young age of 20, died of SUDEP (Sudden Unexpected Death in Epilepsy). Boyce was widely adored and probably best known for his vibrant roles in popular Disney TV shows like “Descendants” and “Jessie,” where his charisma shone brightly for a young audience.

However, what many might not realize is that he also starred as Adam Sandler’s son, Keithie, in the highly lucrative and widely successful “Grown Ups” franchise. This connection brought him into the Sandman’s comedic fold, creating a familial bond onscreen that extended into real life. When speaking to Young Hollywood, the teenage star openly admitted that Sandler was actually the very first person he had been starstruck by, a charming anecdote that highlighted the depth of his admiration for the veteran comedian.

Boyce fondly recalled that since he was only nine years old when they first met, Sandler’s trademark immature jokes and slapstick humor were perfectly suited to his youthful sensibilities: “A nine-year-old likes their fart jokes. So, he’s good at those.” This early bond, however, clearly developed into something much deeper and more meaningful, as the news of Boyce’s passing profoundly impacted the comedian, who took the loss incredibly hard, reflecting a genuine paternal affection.

Sandler poured out his grief and love on his social media accounts, writing a deeply moving tribute: “Too young. Too sweet. Too funny. Just the nicest, most talented, and most decent kid around. Loved that kid.” He continued, expressing the profound sense of loss: “Thank you, Cameron, for all you gave to us. So much more was on the way. All our hearts are broken.” This raw outpouring of emotion underscored the powerful connection they shared. Sandler even ensured Boyce was honored in the credits of his later film, “Hubie Halloween,” where a few minutes after the movie concludes, a poignant picture of the late actor appears on screen, accompanied by a heartfelt message that reads: “You live on forever in our hearts and are truly missed every day.” It was a beautiful and fitting tribute to a bright light extinguished far too soon.

5. **Chris Farley**

Adam Sandler has arguably worked with more top-notch comedians than almost anyone else in the history of Hollywood, making his collaborations legendary. Yet, during the most touching and profoundly heartfelt song of his uniquely musical Netflix special, “100% Fresh,” Sandler sings with a poignant sincerity, “When they ask me who’s the funniest guy I ever knew, I tell ’em hands down without a doubt it’s you.” He is, of course, “singin’ about [his] friend Chris Farley,” a testament to their incredibly close bond and Farley’s unparalleled comedic genius.

Farley and the Sandman were not just colleagues, but incredibly close buddies who came up together on “Saturday Night Live” in the early 1990s, forming a comedic powerhouse. Beyond countless hilarious “SNL” sketches that have become cultural touchstones, the dynamic duo also co-starred together in a string of memorable films, including “Coneheads,” “Airheads,” and the iconic “Billy Madison.” Their synergy on screen was palpable, their improvisational skills legendary, and their shared history undeniable.

In “Billy Madison,” Farley delivered an absolutely scene-stealing performance as the wildly unhinged bus driver, a character so memorable he arguably provided more infamous and quotable lines than any other character in that beloved movie. His raw energy, physical comedy, and sheer commitment to the role cemented his status as a one-of-a-kind comedic talent, leaving audiences roaring with laughter and marveling at his unique abilities. He was a force of nature, a true original whose presence lit up every frame.

As probably everyone now knows, however, Farley’s “wild man” personality, which brought so much joy to millions, tragically came with severe consequences in his personal life. On December 18, 1997, he was found dead in his apartment due to an accidental drug overdose, a devastating loss that shocked the world and left countless fans and colleagues heartbroken. Chris Farley was only 33 years old at the time of his passing, leaving behind a comedic legacy that, though cut tragically short, continues to inspire and entertain, reminding us of the brilliant, explosive talent that was Chris Farley.

6. **Joseph Bologna**

For fans of Adam Sandler’s filmography, 1999’s “Big Daddy” holds a special place, not least because it contains what is arguably one of the most tearjerking and emotionally resonant scenes in any of his movies. In the film, Sandler’s character, Sonny, grapples with an estranged relationship with his father, Lenny, a role beautifully brought to life by the Oscar-nominated screenwriter and accomplished actor Joseph Bologna. Their dynamic formed a poignant emotional core to the otherwise comedic narrative, exploring themes of family and reconciliation.

This strained father-son relationship reaches a critical point when, during a pivotal hearing to determine whether Sonny was indeed a good and fit father to Julian, Sonny makes a deeply vulnerable request: he asks his own father to question him. What unfolds is a truly powerful and emotionally charged scene that, for many viewers, serves as a poignant reminder of the importance of family, perhaps even making you want to call up your own dad and tell him, “I love you.” Bologna’s performance here was understated yet profoundly impactful, lending significant weight to the film.

While “Big Daddy” marked Bologna’s sole appearance in an Adam Sandler flick, it was, without a doubt, an incredibly memorable one. So much so that, when he passed away in 2017, it was arguably one of the parts he was most remembered for by a wide audience, despite the fact that he had been a fixture in TV shows and movies since 1971, accumulating a lengthy and distinguished career. This speaks volumes about the emotional resonance of his “Big Daddy” role.

Joseph Bologna died from pancreatic cancer at the age of 82, leaving behind a legacy as a versatile and respected performer who could seamlessly blend comedy and drama. His contribution to “Big Daddy” added a layer of depth and sincerity that elevated the film, demonstrating that even in Sandler’s often zany world, there was room for profoundly touching human connection. His ability to deliver such a powerful performance in a single role for Sandler truly underscored his veteran acting chops and enduring appeal.

7. **Mary Pat Gleason**

If you were a fan of sitcoms in the 1990s, there’s a very high probability that you had the pleasure of seeing Mary Pat Gleason in action, even if you didn’t know her name at the time. This incredibly talented and prolific actress seemed to be virtually everywhere during that era, gracing huge and popular shows like “Saved by the Bell,” “Friends,” and “Will and Grace” with her distinctive presence and impeccable comedic timing. Her versatility, however, extended far beyond the small screen, as she also starred in a plethora of movies throughout her lengthy and impressive career, ranging from charming teenage romcoms like 2004’s “A Cinderella Story” to weighty historic dramas like 1996’s “The Crucible.”

Despite her great range and ability to tackle various genres, one could easily argue that Gleason’s undeniable forte truly lay in the world of comedy. She possessed a natural and effortless ability to make people laugh, often needing only the briefest of appearances or the simplest of lines to do so. For instance, in the two Adam Sandler movies where she popped up, 2007’s “I Now Pronounce You Chuck and Larry” and 2014’s “Blended,” Gleason had very limited lines – indeed, in “Blended,” she’s only featured in one memorable scene. Yet, despite her minimal screen time, she consistently contributed to some of the films’ biggest and most enduring laughs, showcasing her innate comedic prowess.

What remained largely unknown to most of her adoring public was that Mary Pat Gleason courageously did the majority of her later acting work after having been diagnosed with cancer. She faced her health challenges with incredible strength and resilience, continuing to pursue her passion for performance. Sadly, she ultimately succumbed to the disease at the age of 70 in June 2020, joining a tragic slew of other beloved actors and actresses that the world lost that year, marking a truly difficult period for the entertainment industry.

In a moving statement released via CNN, her manager confirmed the immense strength and unwavering spirit of this incredibly tough woman, noting that Gleason “continued to work on shows like ‘The Blacklist’ and ‘Mom’ even through the pain.” This testament to her dedication and resilience paints a picture of a remarkable individual who loved her craft and faced adversity with grace. Mary Pat Gleason’s ability to bring laughter and warmth to the screen, even in the face of her personal struggles, is a poignant reminder of her enduring talent and the quiet strength of so many unsung heroes of film and television.

Navigating the vast comedic landscape created by Adam Sandler means encountering a constellation of talents, many of whom have left an indelible mark on our screens and hearts. While the first seven actors we explored brought their unique brilliance to the Sandman’s projects, even more iconic figures graced his films, whose passing might come as a surprise. These are the legends whose expansive careers and specific impact echo through Hollywood, reminding us of the enduring power of their craft. Let’s delve into seven more unforgettable talents whose legacies continue to thrive.

8. **Cloris Leachman**

In early 2021, the entertainment world collectively paused at the news of Cloris Leachman’s passing due to natural causes. An absolute titan of acting and comedy, Leachman was an Oscar-winning star who made her screen debut way back in 1947. Over an incredible span of 70 years, she amassed a staggering list of acting credits, appearing in more than 280 films and TV shows.

It’s a delightful tidbit, easily overlooked, that this revered actress, known for iconic roles like Frau Blücher in “Young Frankenstein,” actually graced not one, but two of Adam Sandler’s films. Her versatility shone through in 2004’s moody romantic drama “Spanglish,” where she played Evelyn, Sandler’s alcoholic mother-in-law.

Leachman then brought her comedic genius to 2005’s remake of “The Longest Yard.” She embodied the warden’s assistant, with an hilariously aggressive crush on Sandler’s Paul Crewe. Her ability to pivot between dramatic nuance and hilarious physical comedy demonstrated her unparalleled range.

Upon learning of her passing, Sandler declared her “a true legend” and “one of the funniest of all time.” This high praise, from a comedian who worked with so many A-list talents, speaks volumes about Leachman’s lasting impression, solidifying her status as an enduring comedic force.

9. **Conchata Ferrell**

Conchata Ferrell is iconic as sassy housekeeper Berta on ‘Two and a Half Men,’ but her career was far richer. She starred in popular TV shows and films, including a memorable turn as Jan alongside Adam Sandler in 2002’s ‘Mr. Deeds’. Her no-nonsense demeanor and sharp wit in ‘Mr. Deeds’ provided an authentic comedic layer.

Sadly, Ferrell’s illustrious run closed in October 2020, when she passed away at 77 due to medical complications after a cardiac arrest. Her death prompted an outpouring of grief from fans and colleagues, including ‘Two and a Half Men’ stars Charlie Sheen and Jon Cryer.

Adam Sandler shared a heartfelt message on X: “RIP. Great lady. Will be missed terribly. So sorry to her family.” This tribute underscores the genuine respect she earned. Ferrell’s legacy is a testament to her consistent ability to deliver compelling performances, forever etched in pop culture.

10. **Jerry Reed**

Adam Sandler uniquely blends laughter with sports, and 1998’s “The Waterboy” stands out for quotability. Sandler plays Bobby Boucher, a bullied waterboy who finds his true calling on the football field. Sadly, some talents from this film are no longer with us, including the multi-talented Jerry Reed.

Reed perfectly captured the fiercely competitive spirit of Coach Klein’s nemesis, Red Beaulieu. He brought a powerful, comedic presence to the role, making his character an unforgettable antagonist. His passing in 2008 due to emphysema, a dangerous lung condition, left a void in both acting and music.

Beyond “The Waterboy,” Jerry Reed was an accomplished artist. He starred as Cledus Snow in three ‘Smokey and the Bandit’ films. Reed was also a chart-topping country music star, earning three Grammys and inducted into the Country Music Hall of Fame in 2017. His dual legacy is truly remarkable.

11. **Carl Weathers**

Carl Weathers built an astonishing career with roles in ‘Rocky,’ ‘Star Wars,’ and ‘Predator.’ His portrayal of golf mentor Chubbs Peterson in ‘Happy Gilmore’ stands out, introducing Weathers to a new generation and showcasing his comedic muscles.

Weathers’ impact as Chubbs was so profound that he reprised the role in ‘Little Nicky’ as Chubbs in heaven. Fans eagerly anticipated his return in ‘Happy Gilmore 2’.

Tragically, Weathers did not live to complete ‘Happy Gilmore 2’ or play Chubbs a third time. He passed away on February 1, 2025, from natural causes at 76. His death necessitated extensive rewrites for the sequel, as Sandler confirmed: “We had a painful change, Carl Weathers had a massive part.”

Sandler described Carl’s excitement for the sequel, and how his passing led to rewrites. ‘Happy Gilmore 2’ incorporated archival scenes from the original film, technically his final screen credit. This homage ensures Chubbs Peterson and Carl Weathers remain cherished in the ‘Happy Gilmore’ universe.

12. **Darren McGavin**

Darren McGavin, a venerable actor, notably embodied high-profile patriarchs late in his career. He played the grumpy dad in ‘A Christmas Story,’ and later the wealthy hotel magnate, Brian Madison, in Adam Sandler’s ‘Billy Madison’.

In ‘Billy Madison,’ McGavin delivered a quintessential performance as Brian Madison, the exasperated yet loving father to Sandler’s character. His portrayal anchored the comedic chaos, providing grounded reality. The dynamic between McGavin’s stern father and Sandler’s immature son was comedic gold.

After ‘Billy Madison,’ McGavin added few credits, stepping away from acting. He passed away at 83 on February 25, 2006, from heart disease. His final film, ‘Still Waters Burn,’ released posthumously in 2008, adds a poignant note to his distinguished career. McGavin’s character and gravitas ensured his legacy as a classic Hollywood figure.

“Dean Charles Davis and Richard Griffiths (18415250758)” by Peabody Awards is licensed under CC BY 2.0

13. **Richard Griffiths**

As Adam Sandler’s career matured, he embraced family films, leading to 2008’s ‘Bedtime Stories’ with Disney. Sandler portrays Skeeter Bronson, a handyman whose fantastical bedtime stories mysteriously begin to come true, blurring lines between fiction and fact.

Richard Griffiths memorably played Barry Nottingham, Skeeter’s eccentric boss. In a story, Barry transforms into a king and promises Skeeter a promotion, which fantastically manifests. While ‘Bedtime Stories’ succeeded, Griffiths was also deeply entrenched in ‘Harry Potter,’ beloved for his portrayal of Harry’s cruel uncle, Vernon Dursley.

Beyond these, Griffiths left his mark in films like ‘Withnail and I,’ ‘Chariots of Fire,’ ‘Gandhi,’ and ‘Hugo.’ British audiences cherished his lead role in the 1994 BBC series ‘Pie in the Sky.’ He passed away in 2013 at 65, following complications from heart surgery. His seamless transition across genres testifies to his immense talent and versatility.

Adam Sandler’s cinematic universe is more than just movies; it’s a vibrant tapestry woven with incredible talent, unforgettable performances, and cherished memories. Each actor, from one-off cameos to recurring presences, contributed a unique spark, elevating storytelling and bringing joy to millions. Their physical presence may be gone, but their laughter, tears, and undeniable magic continue to resonate on screen, keeping their vibrant spirits alive. Their legacy, interwoven with Sandler’s own, ensures they remain integral parts of Hollywood’s comedic heart, reminding us that true talent transcends time.