Adam Sandler’s two best movies, according to George Clooney: “I really loved that”
George Clooney has a list of iconic co-stars a mile long.
He’s been adrift in space with Sandra Bullock, married to Meryl Streep in fox form, pulled off heists with Brad Pitt, Matt Damon, and eight others, and (regrettably) battled with Arnold Schwarzenegger and Uma Thurman while wearing an incredibly tight batsuit.
Not long ago, the silver fox himself added a surprising new name to his Rolodex. As part of Noah Baumbach’s upcoming flick Jay Kelly, George Clooney found himself working side by side with none other than Adam Sandler. Due to hit Netflix in November 2025, the film follows Clooney’s character – a washed-up movie star – as he embarks on a tour of Europe with his long-time manager Ron, played by Sandler. What starts as a bit of a jolly quickly turns into a proper soul-searching road trip. A Clooney-Sandler double act on an emotional Euro adventure? Go on, then.
Sandler is an incredibly divisive figure. Once an untouchable superstar with a roster of hits to his name, he’s now the archetypal Hollywood has-been; an annoying hangover of a previous age still coasting on his past glories. Clooney doesn’t think so, however. He clearly has a soft spot for him and some of his works, as he revealed when both parties were interviewed by Empire.
“I thought Punch-Drunk Love was amazing,” he told his colleague. “That was the first time we’d seen you do something where it wasn’t just a straight-up comedy. I also have to say that you were so beautiful in The Meyerowitz Stories. And not just because it’s Noah. I really loved that. I thought you and Ben [Stiller] were great together. I felt like that movie got short shrift. Somehow it didn’t get the attention.”
Punch-Drunk Love routinely comes up in counterarguments against Sandler’s decline. Directed by the esteemed Paul Thomas Anderson, the film sees the comedian play a hopelessly awkward man who ends up embarking on an unlikely love story with his sister’s co-worker (Emily Watson). Nobody expected Sandler to give this sort of performance; earnest, vulnerable, flawed, but likeable. It is often cited not only as his greatest achievement, but also as one of the top entries in the category ‘Comedy Actors Doing Serious Movies’.
The Meyerowitz Stories (New and Selected) was Sandler’s first proper go at working with Noah Baumbach, and it’s a solid reminder that he’s got real acting chops when he fancies using them. He plays one of a group of slightly messed-up siblings reuniting to celebrate their grumpy artist dad, played by Dustin Hoffman. It’s a bit like The Royal Tenenbaums, only with less incest, more stone carving, and Ben Stiller still kicking about for good measure. People never seem to mention it when they talk about Sandler’s “serious” phase – probably because Uncut Gems nicked all the headlines – but honestly, this one’s well worth a watch.
Clooney has routinely come to his co-star’s defence during the press tour for Jay Kelly. There’s every chance that this could just be to promote the movie – he shouted out one of the director’s other movies, lest we forget – but Clooney is a big film fan, so there’s every chance he actually has seen a bulk of Sandler’s work. It would be nice if he were being genuine.
Poor Adam probably couldn’t take the betrayal.
