Onscreen gangsters, real-life civil rights activists, and extraordinary comedians gone
too soon.
Adam Sandler has shared the screen with many legendary entertainers, but do you know who
he considers the funniest?
Here are some of the Sandman's latest and greatest costars.
Although he's almost certainly best known as the notorious steel-toothed Bond villain,
Jaws, from 1977's The Spy Who Loved Me and 1979's Moonraker, Richard Kiel made an unforgettable
appearance alongside Sandler in Happy Gilmore.
At 7 feet 2 inches, Kiel perfectly played the behemoth spectator in the gallery at Gilmore's
tournaments.
Despite his intimidating presence, Kiel's character added a great deal of comedy to
the film by hilariously crossing paths with Gilmore's rival, Shooter McGavin, played by
Christopher McDonald.
Apparently, he and Sandler developed a great bond while on set.
When Kiel passed away in September 2014, Sandler mourned the loss of his pal on Twitter, saying,
"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."
It is believed that the towering actor died of a heart attack, but TMZ also reported a
death certificate indicating that he also had coronary artery disease.
Regardless of the cause of his ultimate demise, Kiel will always be remembered as one of the
greatest of Hollywood's giants.
Ray Liotta's death in May 2022 rocked the world.
The mega-talented actor, best known for playing protagonist Henry Hill in Martin Scorsese's
1990 gangster classic Goodfellas, passed away in his sleep while working on the upcoming
movie Dangerous Waters.
He was 67 years old, with a slew of movie credits and impressive awards, including an
Emmy win for Outstanding Guest Actor in a Drama Series thanks to his work in ER.
While Liotta's death is pretty common knowledge at this point, some fans might be surprised
to learn that he actually starred in one of Adam Sandler's Netflix movies before he died.
In 2020's Hubie Halloween, the Shades of Blue actor played Pete Landolfa, one of Hubie's
many bullies.
"He did love to laugh.
Okay.
And I know he would get a great chuckle out of this."
Although Liotta's character in the flick was a major jerk, Sandler noted that he was the
polar opposite in real life.
After the actor's death, Sandler took to Twitter to memorialize his friend.
He expressed appreciation for Liotta's acting, as well as his parenting and sense of humor.
It seems the on-screen tough guy was quite the renaissance man.
One could argue that some of Sandler's best works are the romantic comedies he stars in
alongside Drew Barrymore. 1998's The Wedding Singer, 2004's 50 First Dates, and 2014's
Blended are all heartwarming and hilarious films where the stars bring out the best in
each other.
Notably, Barrymore and Sandler were almost always joined by another actor when they teamed
up for these movies: Alexis Arquette.
Arquette was a talented character actor and a major transgender activist who transitioned
into a woman in 2004.
Sadly, she passed away in late 2016 after suffering a heart attack while also stricken
with AIDS.
In their statement about her death, her siblings Patricia, Rosanna, Richmond and David Arquette
praised her for living her truth, saying,
"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."
Arquette's final appearance in a feature film before she died was actually Blended, wherein
she had a brief cameo as Georgina Stitzer, an homage to the character she played in The
Wedding Singer.
In both movies, she played a Boy George impersonator, and she actually did it so well, George himself
tweeted that she was, quote, "another bright light gone out far too soon" when he learned
of her passing.
While losing someone always hurts, there's arguably nothing worse than losing someone
who still has a whole life ahead of them.
That's precisely what happened to Disney Channel breakout star, Cameron Boyce, who in 2019
died of Sudden Unexpected Death in Epilepsy at the young age of 20.
Boyce was probably best known for his roles in Disney TV shows like Descendants and Jessie,
but he also starred as Adam Sandler's son, Keithie, in the highly lucrative Grown Ups
franchise.
When speaking to Young Hollywood, the teenage star admitted that Sandler was one of the
first people he felt starstruck by.
Boyce noted that when he first met Sandler at age 9, the older actor's trademark immature
jokes were right up his alley.
"I knew of him very well.
A nine year old likes their fart jokes, so, he's good at those."
However, that bond clearly developed into something deeper, as the comedian took Boyce's
passing incredibly hard.
On social media, Sandler expressed how heartbroken he was that such a kind and talented young
actor passed away so early into his career.
Sandler even honored Boyce in the credits of Hubie Halloween.
A few minutes after the film ends, a picture of the late actor appears on the screen, as
well as a heartfelt tribute which reads:
"You live on forever in our hearts and are truly missed every day."
It's possible that Adam Sandler has worked with more top-notch comedians than anyone
else in Hollywood history.
However, during the most touching song of his uniquely musical Netflix special, 100%
Fresh, he poignantly sings that he considers Chris Farley the funniest person he's ever
worked with.
Farley and the Sandman were incredibly close buddies.
They came up together on Saturday Night Live in the early 1990s.
Outside of countless hilarious SNL sketches, the duo co-starred together in Coneheads,
Airheads, and Billy Madison.
In Billy Madison, Farley absolutely steals every scene as the wildly unhinged bus driver,
arguably providing more infamous lines than any other character in that movie.
The man was truly a one-of-a-kind comedic talent.
"Everybody on?
Good.
Great.
Grand.
Wonderful.
No yelling on the bus!"
Tragically, many comedy fans know that Farley's "wild man" personality came with great consequences.
On December 18, 1997, he was found dead in his apartment due to an accidental drug overdose.
He was only 33 years old.
1999's Big Daddy has one of the most tear jerking scenes in any Adam Sandler movie.
In the film, it's established that Sandler's character, Sonny, has an estranged relationship
with his father, played by Oscar-nominated screenwriter and actor Joseph Bologna.
The characters' relationship is tested when, during a hearing to establish whether or not
Sonny was a good father to his adopted son, Julian, he asks his dad to question him.
It's a truly powerful scene that still tugs on the heartstrings of many fathers and sons
today.
While Big Daddy was Bologna's only appearance in a Sandler flick, it was most definitely
a memorable one.
So much so that, when Bologna passed away in 2017, many people celebrated the role specifically,
despite the fact that he'd been starring in TV shows and movies since 1971.
According to The Hollywood Reporter, Bologna died from pancreatic cancer at the age of
82.
If you watched any sitcoms in the 1990's, there's a good chance you saw Mary Pat Gleason
in action.
The talented actress was seemingly everywhere during that era, appearing in huge shows like
Saved by the Bell, Friends, and Will and Grace.
She also starred in a plethora of movies throughout her lengthy career, ranging from teenage romcoms
like 2004's A Cinderella Story to historic dramas like 1996's The Crucible.
Although she had great range, Gleason's forte was in the world of comedy.
She just had a natural ability to make people laugh, and she didn't need a big part to do
so.
For example, in the two Adam Sandler movies she popped up in, 2007's I Now Pronounce You
Chuck and Larry and 2014's Blended, Gleason's lines were very limited.
However, she still contributed to some of the films' biggest laughs.
"Good morning uncle Chuck."
"What's it doing, guys?"
"Good morning, Teresa."
"Good morning."
Unknown to most, Gleason did most of her later acting after being diagnosed with cancer,
and she ultimately succumbed to it in June 2020, joining a slew of other actors and actresses
that we lost that year.
In a statement, her manager confirmed that she was an incredibly tough woman, fighting
through her pain to finish out her roles in Mom and The Blacklist.
She is most certainly missed.
In early 2021, the world was rocked with the news that Cloris Leachman, treasured actress
and comedian, had passed away due to natural causes.
Over the course of the Oscar-winning star's 70 year career, Leachman earned more than
280 film and TV credits.
In the process, she performed alongside some of Hollywood's most elite celebrities, including
Gene Wilder to Paul Newman.
Another one of Leachman's reputable costars was Adam Sandler.
It's easy to forget that the Young Frankenstein actress actually popped up in not one, but
two of the Sandman's movies.
In 2004's moody romantic drama, Spanglish, Leachman played Evelyn, Sandler's alcoholic
mother-in-law.
One year later, she took on a small but quite hilarious role in 2005's remake of The Longest
Yard, wherein she played the warden's assistant with an especially aggressive crush on Sandler's
character, Paul Crewe.
The pair had a natural chemistry that apparently extended even after the cameras stopped rolling.
When Sandler learned of Leachman's passing, he tweeted a memorial to her, which said,
"Cloris Leachman.
A true legend.
One of the funniest of all time.
And such a great lady.
Loved her.
Will be missed terribly."
That's quite high praise coming from someone who has made movies with so many A-list comedians
throughout his career.
Although she's likely best known for playing sassy housekeeper Berta in over 200 episodes
of Two and a Half Men, Conchata Ferrell starred in loads of popular movies and TV shows throughout
her decades-long acting career.
Her filmography boasts credits from popular shows like L.A. Law, Buffy the Vampire Slayer
and Grace and Frankie, and she was even nominated for Emmy awards on three separate occasions.
She also starred as the no-nonsense Jan alongside Adam Sandler in 2002's quirky comedy, Mr.
Deeds.
Ferrell's great run all came to an end in October 2020, however, when she passed away
from medical complications at the age of 77 following a cardiac arrest.
Some of her old costars and celebrity friends took to social media to express their sympathy
over the terrible news, including Two and a Half Men stars Charlie Sheen and Jon Cryer.
Sandler himself even posted a tweet celebrating the actress and extending his condolences
to her family.
One of Adam Sandler's many talents is his ability to seamlessly combine laughs and sports.
With films like Happy Gilmore and The Longest Yard, the Sandman has been responsible for
helping create some of the most memorable sports comedies of all time.
However, his most quotable sports movie was easily 1998's timeless classic, The Waterboy.
Sandler stars as good-hearted momma's boy Bobby Boucher, an oft-bullied waterboy for
the University of Louisiana football team.
After he's fired from UL, Bobby's given a second chance by Coach Klein, played by Henry
Winkler, and his South Central Louisiana State University Mud Dogs, where he learns that
his place on the gridiron is actually on the field.
Sadly, some members of the iconic cast are no longer with us.
Jerry Reed, who perfectly captured Coach Klein's fiercely competitive nemesis, Red Beaulieu,
passed away in 2008 due to emphysema, a dangerous lung condition.
Reed was not only a talented actor, starring as Cledus Snow in three Smokey and the Bandit
films, but also a chart-topping country music star.
During his music career, he took home three Grammy awards, and was even inducted into
the Country Music Hall of Fame in 2017.
Talk about an impressive legacy to leave behind!
You might not know it from his small role as the frequently intoxicated Mr. Herlihy
in Big Daddy, but Edmund Lyndeck was once a big-time Broadway star.
He was actually the very first actor to bring the evil Judge Turpin to life in Stephen Sondheim's
timeless revenge musical, Sweeney Todd: The Demon Barber of Fleet Street.
He went on to star in several other plays during his time on stage.
While Broadway was clearly his forte, Lyndeck did dip his toes into film and television.
He popped up in small roles in Disney's Enchanted and the raunchy teen comedy, Road Trip.
He also appeared in a few TV shows, including an episode of Law & Order: Special Victim
Unit.
Notably, Big Daddy wasn't the only time he collaborated with Sandler.
Nearly a decade later, Lyndeck also made a cameo in 2008's You Don't Mess With The Zohan.
According to Playbill, Lyndeck passed away on December 14, 2015 at the age of 90, though
the cause of death was not specified.
Check out one of our newest videos right here!
Plus, even more Looper videos about Adam Sandler movies are coming soon.
Subscribe to our YouTube channel and hit the bell so you don't miss a single one.