Adam Sandler’s latest 2025 Netflix release , Jay Kelly, has him paired with a co-star I didn't have on my bingo card, George Clooney, but I’m all for it. In the film, Sandler and Clooney play out the deep friendship between a famous actor and his agent during their European travels. In real life, Clooney and Sandler have been friendly for some time but, early on, one of their outings served as a truly humbling experience for the latter.
Given Adam Sandler and George Clooney were actors who dominated in the ‘00s, I’m surprised it’s taken them this long to work on a film together. Both stars reflected on their relationship while speaking with The New York Times and recalled that they first met after Clooney hosted SNL in 1995. Around that same time, Sandler -- a breakout cast member on the show -- believed he was “becoming a star” until the pair attended a New York Knicks game:
