Adam Sandler's Most Awkward Moments Ever

Whether he's yelling in people's faces in full-on angry manchild mode, offering them a fight, or giving them the kind of derogatory nicknames you'd expect from a school playground, Adam Sandler's brand of comedy thrives on making those around him feel uncomfortable, unsettled, and downright awkward. But perhaps in a case of karma biting him on the proverbial, the star of comedy classics "Happy Gilmore," "The Wedding Singer," and "The Waterboy" has regularly been on the receiving end of such embarrassments in real life.

Indeed, over the years, Sandler has had to deal with everything from disgruntled parents and scathing critics to oblivious waitresses and protesting Native American actors away from the cameras. And often, these difficult encounters will be of the Happy Madison producer's own doing. Here's a look at 11 times when the Hollywood funnyman, along with those in his vicinity, no doubt wished that the ground would swallow him up whole.

From Drew Barrymore in "The Wedding Singer" and Jennifer Aniston in "Just Go with It" to Winona Ryder in "Mr. Deeds" and Marisa Tomei in "Anger Management," Adam Sandler has had to lock lips with some of the most famous and lusted-after women in Tinseltown. But as a happily married man, the comedian claims he finds his on-screen smooches to be awkward.

In a joint interview with Aniston for W magazine, Adam disputed his co-star's claim that he's a good kissing partner, responding, "She would try to protect me. I'm never excited for romantic scenes." Luckily, the star doesn't have to worry about any jealousy from his other half, Jackie Sandler. He added, "My wife loves the women I work with. She's always saying, 'Come on, make sure you kiss the best you can.'"

Jackie might not have any qualms about seeing her husband pucker up with other women in public, but as you'd expect, their daughters Sadie and Sunny Sandler do. During an appearance on "The Jennifer Hudson Show," Adam explained, "When I have to kiss anybody, they're not thrilled about that. But my wife is always telling them, 'It's OK. It's part of the job. Let daddy kiss.' ... Sadie was always fine with it. Sunny would always be going over to my wife, saying, 'You have to watch them. That's not good. I don't like that.'" The star also insisted he remains tight-mouthed, something which Hudson, who starred alongside him in "Sandy Wexler," confirmed. 

You might expect that a celebrity of Adam Sandler's stature would be able to walk into any Michelin-starred restaurant and instantly be given the best table in the house. But in 2021, the A-lister was told he'd have to wait half an hour to be seated at an IHOP.

The waitress who delivered the news failed to recognize the "Uncut Gems" star at the time. But once the truth emerged, she took to TikTok to humorously apologize to the Hollywood star for her lack of five-star treatment. Dayanna Rodas even included CCTV footage of the moment in question to prove her story, captioning it, "Pleaseee come back." Luckily, Sandler didn't take the snubbing to heart, responding on X, formerly known as Twitter, "For the record, I only left the IHOP because the nice woman told me the all-you-can-eat deal didn't apply to the milkshakes." In her defense, even the biggest Sandler fans may have failed to spot they were in the presence of comedic royalty. Not only was the funnyman sporting a bushy beard, but he was also dining at a time when face masks were required.

But this wasn't the end of the story. Just a week later, Sandler returned to the same IHOP on the same day as a Milkshake Monday promotion designed to raise funds for the Comedy Gives Back charity. As you'd expect, Rodas documented the unexpected reunion online, accompanied by the American Authors' feelgood hit "Best Day of My Life."

Contrary to his on-screen persona, Adam Sandler appears to be a relatively calm, composed, and courteous man in real life. Indeed, as a happily married father of two, he's largely managed to keep himself out of the tabloids during his decades-spanning career. But in 2017, the funnyman made headlines for all the wrong reasons following a visibly awkward appearance on Britain's No. 1 chat show.

Sandler was accused of getting a little too overfamiliar with fellow guest Claire Foy when he continually positioned his hand on her leg while being interviewed together on "The Graham Norton Show." Not only did "The Crown" star seem to look uneasy with the gesture, but Emma Thompson, who was sitting on the other side of the comedian, also appeared to glance at his behavior unfavorably.

Following an internet pile-on, a spokesperson for Foy insisted in a statement (via Yahoo! News) that things had been blown out of proportion: "We don't believe anything was intended by Adam's gesture, and it has caused no offence to Claire." A representative for Sandler, meanwhile, also argued that it was a sign of friendliness, pointing out that the actor had done the same thing on "The Tonight Show Starring Jimmy Fallon" while next to Dustin Hoffman.

In 1996, "The Price Is Right" presenter Bob Barker made a rare big-screen appearance in "Happy Gilmore," playing himself as the unfortunate celebrity paired with Adam Sandler's titular crazed golfer in the Pepsi Pro-Am tournament. Following the shoot, the unlikely duo also went out to dinner together. Unfortunately, the film's leading man, just like his character, soon made things awkward.

Sandler recalled the incident while guesting on the "Late Show with David Letterman," explaining, "I sat next to him, and he's a big animal rights activist. And I forgot. But I ordered chicken marsala, and I was sitting next to him eating chicken, and he was eating his pasta with vegetables on top." The comedian added, "I started feeling guilty because I remember once I had my chicken, he'd look at me like, 'Why? Why do you hurt the chicken? ... That chicken has a family.'"

The quick-witted Sandler then quipped, "You can tell the family that they raised a tasty little chicken." While the funnyman's story was unlikely to endear him to PETA, it didn't appear to offend Barker. In fact, the pair remained friends despite the uncomfortable dinner, as evident by Sandler's glowing tribute following the TV legend's death. "The man. The myth. The best. Such a sweet funny guy to hang out with," he wrote on X in August 2023. "Loved talking to him. Loved laughing with him. Loved him kicking the crap out of me."

We're not sure this story of inappropriate workplace behavior would land quite as well a decade on. But back in 2013, Adam Sandler thought nothing of recalling the moment he tried to catch his "Grown Ups 2" co-star, Shaquille O'Neal, in the shower.

Appearing on the talk show "Conan," Sandler explained how his idea came about. "We play basketball. We gotta get back to the movie set. Shaq has to take a shower. So, everyone's like, 'Alright, we'll see ya later, Shaq.' In my head, I'm like, 'I've gotta see [Shaq naked].' ... I can't pass up that opportunity." The actor then walked through the moment he walked to the nearby locker room shower O'Neal was lathering up in.

Luckily for the NBA star, he had some protection. Sandler said, "His bodyguard is there. His bodyguard is just so strong and big. He has a thick neck, bald head, and this one eye. He's looking at me with this one eye. So, I said, 'Sorry. I was just trying to see Shaq's penis. I apologize, and I'm outta here. Please don't tell Shaq.'" O'Neal did eventually find out about this peeping Tom mission, but thankfully for Sandler, he took it all in good humor.

It's fair to say that Adam Sandler isn't exactly a critical darling. The funnyman has enjoyed the odd glowing review, usually when he plays against his type in more serious-minded movies such as "Punch-Drunk Love," "The Meyerowitz Stories," and "Uncut Gems." In fact, he was even tipped to bag an Academy Award nomination for his performance in the latter tense thriller. But his own Happy Madison Productions are generally lucky to receive two stars.

Luckily, Sandler can usually brush off any sideswiping when it's aimed directly at him. But thanks to his habit of casting his nearest and dearest, he finds it much harder when the negative comments affect his co-stars. In a 2015 chat with one-time nemesis Howard Stern (via the Daily Mail), the comedian admitted, "The bad reviews that I get on everything I do, that part pisses me off because I ask my f***ing friends to be in it."

Sandler, whose lowest scoring Rotten Tomatoes rating is the dreaded 0% for "The Ridiculous 6," went on to add, "I'm promising them, 'I think it's good.' And then I do screenings for an audience and it all works, and I'll call them up after and say, 'Hey, that one thing you said really did great.'" He continued, "And then that Friday, every Friday, literally every one of my movies is destroyed."

Adam Sandler didn't exactly help dispel his overgrown manchild reputation with the way he celebrated inking his lucrative deal with one of the world's biggest streaming giants. Indeed, in a 2014 statement (via Fast Company), the funnyman joked, "When these fine people came to me with an offer to make four movies for them, I immediately said yes for one reason and one reason only ... Netflix rhymes with Wet Chicks."

Yes, that was a quip made by a man who was in his late 40s at the time. Understandably, Sandler received some pushback for his fratboy sense of humor, most notably from Rose McGowan. "I mean, what? What in the f*** is going on? No!" the "Scream" star responded in a 2015 interview with Entertainment Weekly.

McGowan had previously called out Sandler on X for the casting note she received for one of his films, which advised female auditionees to enhance their cleavage by sporting pushup bras. The #MeToo activist later told EW, "I was offended by the stupidity more than anything. I was offended by the fact that went through so many people's hands and nobody red flagged it." She added, "This is normal to so many people. It was probably even a girl that had to type it up. It's institutionally OK." McGowan admitted she found it strange that the offer for the part even came her way, adding with a laugh, "I don't think I'm a natural pairing. My thing is, watch out what you ask for."

Remember the dodgeball scene in one of Adam Sandler's earliest box office hits, "Billy Madison"? And remember how the titular character makes several kids wince in pain as his dodgeball throws strike them in the face, stomach, and various other body parts? Well, it turns out at least some of those noises were for real.

In a 2017 chat on "Conan," Sandler revealed that he incurred the wrath of several concerned parents after taking all the dodgeball action a little too seriously: "I hit some kid pretty hard, and he gets upset and he starts crying, and then parents all come up to me." He then explained to them, "'That's the scene. I'm a big guy, went back to school, I'm supposed to plug all of these kids. ... Didn't they read the script?'"

Despite being reminded that most of the kids were too young to read, Sandler remained unapologetic. In fact, he continued on the offense, adding, "I think I told the guys to roll anyways, and I nailed a bunch of kids, something awful like that. But those kids grew up and guess who they are today? I don't know."

In 2015, after years of turning down invitations, Adam Sandler finally agreed to appear on the Sirius XM show hosted by his former nemesis, Howard Stern, as previously mentioned. And although the pair ended up burying the hatchet for good, things still got a little awkward during the eagerly awaited encounter.

None more so than when Stern recalled traveling on the same flight as Sandler, only for the "50 First Dates" star to completely ignore him. The latter explained (via the Daily Mail), "That was after you were nasty to me, and I remember the next day you talked about me being an a**hole again. But the reason I didn't say hello was you were saying s*** to me."

Stern had previously moaned about the fact that Sandler had repeatedly snubbed offers to guest on his radio show, claiming that he wasn't the only vocal critic of the "Saturday Night Live" alum's movies. But the big-screen funnyman explained there was a valid reason why he'd been so affected by such comments: "When I was at NYU freshman year, I loved you. That's why it was weird when you used to slam me. It would break my heart because I loved you growing up."

Four years before producing and co-starring in the 2023 comedy "You are So Not Invited to My Bat Mitzvah," Adam Sandler discussed his daughter Sadie's impending real-life ceremony during an appearance on "The Ellen DeGeneres Show." But when their talk inevitably turned to the subject of her dating, the "Sandy Wexler" star ended up creeping the host out.

Sandler said, "You know, I drive around with [Sadie and] her friends, and I hear them talking about boys now. It's amazing, the feelings I had about the same boys like five years ago, when they would mention the kid's name, I'd be like, 'I love that kid.' Now, I get very jumpy." The funnyman then joked about the effects of puberty before the conversation became a little awkward.

"I see them make eye contact with my kid — it's very weird to see your kid lock eyes with a boy while they're talking. Just Like, 'Whoa, you lock with Daddy's eyes,'" Sandler said, half-joking about his over-protectiveness as a father. When DeGeneres pointed out that his tactics are "kinda creepy," her guest agreed, responding, "That's a good one, Ellen, you're right, that is gross. ... Not lock, I just say, 'Engage with Daddy.'" Whether that's any less creepy remains to be seen.

Adam Sandler fans may have been a little perturbed when they switched on "Good Morning America" in 2022 to see the funnyman with a black eye. But as the "Punch-Drunk Love" star soon revealed, there was a completely innocuous, if still painful, reason for his facial injury.

Sandler explained, "I was in bed in the middle of the night. You know how they tuck in your sheets at the bottom, some people? Somebody tucked in the sheets too much, I had my phone in the middle of the bed, I kicked my feet up to untuck it — the phone went flying, hit me in the head." The comedian also revealed that instead of tending to the wound and the blood pouring out, he simply went back to sleep due to his overly tired state. While some may think the shiner "looks so cool," the "Hustle" star quipped of the story, "There is nothing cool about this thing."

Remarkably, other accidents had previously caused Sandler to go on television with a black eye — not once but twice. He showed up on "Jimmy Kimmel Live!" with a similar blemish while promoting "Pixels" in 2015, this time caused by a flying elbow in a basketball game. A year prior, the "Blended" star sported an impressive shiner during an interview on "The Tonight Show Starring Jimmy Fallon." At the time, Sandler joked that the pregnant belly of frequent co-star and fellow guest Drew Barrymore had been responsible, but the real reason has since remained a mystery.