Adam Sandler arrived at his Happy Gilmore 2 premiere in New York City on Monday just as we’d expect, dressed in a floral shirt and salmon-coloured basketball shorts, smiling next to his wife of 21 years, Jackie, and their two teenage daughters, Sunny and Sadie. And he was ready with kind words for someone who meant a lot to him.
One of Sandler’s earliest roles was on The Cosby Show, playing a friend to Theo Huxtable, played by Malcolm-Jamal Warner – who died in a drowning accident the day before the film premiere. “Malcolm was so nice to me,” Sandler said. “I was 18 and Malcolm was probably 17, we would take walks together and pick up food, talk, play basketball, hang out on the weekend, go to parties together. Malcolm was a true great person, hilarious, smart kid and meant a lot to America.” Later that night, Sandler sat in the audience at The Late Show With Stephen Colbert – along with the hosts of all the other late-night talk shows – to give his fellow comedian post-cancellation-announcement support.
In good times and bad, Sandler shows up and strikes the right note. He may have started out as a goofy kid on Saturday Night Live, putting a spoon on his nose and calling it a Halloween costume, but these days he’s grown into one of Hollywood’s few remaining bankable stars that you’re always genuinely happy to see: ridiculously charming in that relatable, down-to-earth dad sort of way.
We’re all hip to the Adam Sandler film cycle: a sequel with his buddies; another mystery with Jennifer Aniston; an animated flick where he might voice a septuagenarian lizard or an overprotective Dracula dad; a dramatic turn that deserves an Oscar nomination but never gets one; and, in the last few years, a heartwarmer co-starring his teenager daughters, Sunny and Sadie. (Sometimes it’s a mash-up: Happy Gilmore 2 (July 25) is both a sequel with his friends and a family collab, as Jackie and the girls appear in the movie.) It’s all comfort viewing, but not exactly must-watch – save for a couple of those dramas.
For fans who’ve grown up with Sandler, it doesn’t really matter if this return to his hot-headed hockey-player-turned-pro golfer character in Happy Gilmore 2 is a hole-in-one or a scratch because the real-life Sandman is already way ahead on the comedic scorecard of 2025 – thanks to his appearances at the Golden Globes, Oscars, Conan O’Brien’s Mark Twain Prize ceremony and the Saturday Night Live 50th anniversary special.
During her Golden Globe monologue, host Nikki Glaser namechecked Sandler while teasing Timothée Chalamet: “Timothée, you’re just so great at playing these beloved eccentrics. Dylan, Willy Wonka, who’s next? Adam Sandler?” But then it hit her, the name Chalamet is similar to the Cajun-esque gibberish words Sandler would likely use as a silly greeting, like “A Chalamet to you!” Finding Adam in the audience, she asked him to give her a quick “Chalamet,” and, of course, he acquiesced, bringing the house down with his off-the-cuff vocal stylings. (Turns out, Timothée and Adam are friends who play pickup basketball together.)
At the Oscars, Sandler did a call-back, running up to the young actor, who was sitting in the front row, and grabbed his face for a joyous Chal-a-maaaaaaaay. This came at the end of a whole other hilarious bit in which that night’s host, Conan O’Brien, embarrassed Sandler for being “dressed like a guy playing video poker at 2 a.m.” Wearing his usual hoodie over a Hawaiian shirt, long basketball shorts and sneakers, Sandler shot back, “You know what Conan, I like the way I dress. Because I’m a good person … Do my snazzy gym shorts and fluffy sweatshirt offend you so much that you have to mock me in front of my peers? I’m going.” As he leaves the theatre, he invites the audience to a game of five-on-five basketball at Veteran Park, midnight tip-off – and many people in that room would have loved to follow him out.
Sidenote: Sandler’s wardrobe has been a going concern in Hollywood and with the media for years. Back in 2021, at the height of the pandemic, Vogue named him “fashion icon of the year,” noting that “Adam Sandler beat out Harry Styles, Lizzo and Britney Spears to be the top search for celebrity style.” And now he’s won over a whole generation, says GQ. “After years of being clowned on as one of the worst-dressed celebrities, Sandler has emerged as a singular style icon,” the magazine said just last year. “Gen Z eats his big-shirt-big-shorts-mismatched patterns vibe up with zero irony – or maybe so much irony it just circles back around to a kind of warped sincerity.” Turns out, Canada even plays a big part in Sandlercore. When the actor was asked who or what he’d bring if he was relocating to outer space, he quickly replied, “Probably a lot of Roots sweatshirts, I like the way they fit. I like the way they keep me warm up in space.”
But he cleans up nice when he’s showing up for someone else. When Conan O’Brien received the Mark Twain Prize at the Kennedy Center this year (an honour Sandler was given in 2023), Sandler arrived in a perfectly tailored suit and killed it with a faux-arrogant bit on the differences between the Sandman and his buddy (and neighbour) Conan. “Gets mistaken for a young James Caan: Sandman; Gets mistaken for one of those blow-up thingies outside a car dealership: Conan,” he joked. “Can walk in and get a table at any restaurant in the world: Sandman. Can walk in and get a table at Panda Express in the mall if he gets there a half hour early and, to be honest, on Fridays it’s still iffy: Conan.” Of course, Sandler followed it up with words from the heart: “You’re faster than all of us, you’re nicer than all of us, and I’m so happy this life was yours, buddy.”
O’Brien was a writer on SNL when Sandler arrived in 1990 and started taking notes. At 30 Rock, the younger comedian fine-tuned his silly voices, temper-tantrum-like yelling, wacky accents and gibberish talk, becoming the ultimate class clown on the show – during an era often described as “the Frat Boy years” – alongside Chris “In a Van Down By the River” Farley, David “Buh-Bye!” Spade, Rob “Makin’ Copies” Schneider and Chris “I’m Chillin’” Rock. These media-dubbed “Bad Boys of SNL” became lifelong friends (although Farley died in 1997) and the stars of one of Sandler’s most successful franchises: Grown Ups.
In those early years, Sandler had a few recurring SNL skits, including the “Herlihy Boy” who just wants to stay at your house when you’re on vacation, and Brian, host of “The Denise Show,” who repeatedly melts down on his cable access call-in program while discussing his recent breakup with his girlfriend of eight months: “If you’re just tuning in, we’re taking calls, tonight’s subject is Denise. Have you seen her? Has she said anything about me?” This is the skit that inspired celebrated indie director Paul Thomas Anderson to write Punch Drunk Love for Sandler, allowing him to prove his dramatic chops, which we’d see again in the Safdie Brothers’ 2019 crime thriller Uncut Gems.
Also at SNL, Sandler diligently worked on his schticky songs, with odes to his red-hooded sweatshirt (“What is it about you that makes me so jolly? / Is it your 50 cotton or your 50 poly?”) and Thanksgiving (“I love to eat the turkey at the table / I once saw a movie with Betty Grable”). But it was The Chanukah Song that revealed a new kind of authentic, endearing sweetness and vulnerability that Sandler could pair with his brash bro-ness. “When I was a kid, this time of year always made me feel a little left out because in school there were all these Christmas songs and all us Jewish kids had was the song Dreidel Dreidel Dreidel,” Sandler said in his intro to the tune. If there had been viral videos back in 1994, this would have broken the Internet: “Chanukah is the festival of lights / Instead of one day of presents, we have eight crazy nights / When you feel like the only kid in town without a Christmas tree / Here’s a list of people who are Jewish just like you and me.” He then revealed that David Lee Roth lights the menorah and that “Paul Newman’s half Jewish, Goldie Hawn’s half too / Put them together, what a fine lookin’ Jew.”
A year later, he was off the show. “I was fired, I was fired,” Sandler explained in a monologue song when he returned to SNL as the host in 2019. “NBC said that I was done / Then I made over 4 billion dollars at the box office / So I guess you could say I won.”
Monetarily speaking, Sandler is the most successful SNL alumnus – there are 167 of them. And when all those former cast members came together for SNL50 earlier this year, it was Sandler that took home the unofficial title of best performer of the night. Walking into the anniversary event, he was his calm, cool and collected self. When asked before the show about his favourite sketch of all time, Sandler said, “I always loved Dan Aykroyd’s Fred Garvin [Male Prostitute],” giving props to the Canadian comedy legend from the original cast. “Me and my friends used to do that around the house, that’s a good one.”
Then, in front of the likes of SNL greats like Bill Murray, Eddie Murphy and Tina Fey – and seemingly every A-lister who ever hosted the show – Sandler took to the stage. He could have whipped off an Opera Man or Canteen Boy skit, but instead he came out as himself, grabbed his guitar and did what he does best, a tribute song: “50 years / Saturday Night Live’s been on for 50 years … 50 years of Tuesday late night pizza / 35 years of Pepto Bismol from Nurse Theresa … 50 years of cast members saying I think our cast is the greatest of all time / But we all know that the first cast was the best.” He even choked himself up with his shoutouts to his late buddies. “Six years of our boy Farley / five of our buddy Norm [Macdonald] / 50 years of one of us getting to say ‘Live From New York, It’s Saturday Night’ / 50 years of standing on home base, waving good night and goodbye / 50 years of the best times of our lives.”
And it’s been 33 years of Adam Sandler ditties that have graduated from novelties to Emmy nominees, as that SNL50 song is recognized in this year’s Outstanding Original Music and Lyrics category. “Only Sandler could do that,” former SNL star Dana Carvey told the Washington Post about his buddy’s musical numbers, like the devastatingly poignant one he wrote for Farley that Sandler often sings with a lump in his throat. “That’s another gear that Adam has. He’ll be really, really silly. But he’s not afraid to go for sentimentality and earnestness.”
This year has already been a standout one for Sandler and it wouldn’t surprise us if at the Emmys he finally gets an award from his peers (to put next to his 12 Kids’ Choice Awards). Let us anticipatorily say, “Congratulations Adam – a Chalamet to you!”
Lead collage photo credit: L to R: Adam Sandler at the premiere of ‘Happy Gilmore 2′, July 21, 2025 (Netflix); in a still from the film (Netflix); in the original ‘Happy Gilmore’, 2010 (Canadian Press); Sandler in 2023, New York City (Jason Howard/Bauer-Griffin/GC Images)
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