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It’s become an affectionate running joke over the years that Christopher Nolan has a regular cast of actors he routinely casts in his movies. The likes of Michael Caine, Cillian Murphy, Tom Hardy, Christian Bale, Anne Hathaway, and Matt Damon have all returned to Nolan many times and experienced great success. In truth, though, Nolan isn’t the only person in Hollywood who does this. After all, how many times have Spike Lee and Antoine Fuqua cast Denzel Washington, and how many more collaborations could Martin Scorsese and Leonardo DiCaprio have in them?
There is one person in the business whose drive to work with the same people over and over again arguably exceeds even these luminaries, though. This man became the highest-paid actor in Hollywood in 2023 despite not appearing in a theatrically released film in nearly a decade. For years, people joked that this star seemed to only make movies so he could hang out with his pals in exotic locations – and in 2015, Adam Sandler pretty much admitted this was the truth.
When speaking with Howard Stern about why he makes so many movies with his longtime comedy buddies Kevin James, David Spade, Chris Rock, and Rob Schneider, the mind-bogglingly successful star confessed the answer is simple. “I grew up with these guys,” he shrugged. “We have such a great time together. And, honestly, life’s short. Why not do what makes you happy with people you love?”
Sandler’s usual comedy repertory company also includes the likes of Maya Rudolph, Drew Barrymore, Nick Swardson, Tim Meadows, and Andy Samberg. However, there is one actor whose time in the Sandler trenches eclipses everyone else – and that is Steve Buscemi.
Sandler first worked with beloved character actor Buscemi in 1994’s Airheads, and they must have struck up quite the relationship because the Fargo star has lent his talents to 16 Sandler movies in total. He doesn’t tend to have big roles in the films but will reliably show up for a short cameo or small supporting turn.
Buscemi’s most memorable Sandler appearances include Billy Madison, The Wedding Singer, Mr Deeds, Big Daddy, Grown Ups, and Hotel Transylvania. In fact, Sandler once revealed all he had to tell ‘The Boosh’ – his inexplicable nickname for Buscemi – about Hubie Halloween, their 16th collaboration, was that he’d be playing his neighbour. Buscemi immediately said, “You just tell me when.” In truth, the acclaimed actor’s consistent involvement in Sandler movies is always a fun curiosity because, as he joked when presenting The Kennedy Center’s Mark Twain Prize to Sandler in 2023, “I was a serious actor before I met you, man!”
Which filmmaker has directed the most Adam Sandler movies?
Sandler doesn’t just ensure he works with the same actors over and over again, though – he also has his preferred filmmakers, too. From the moment he started Happy Madison Productions in 1999, Sandler has built a family of directors, writers, and crew members who all consistently work on his films. As Buscemi marvelled, “He does this for all his friends. He does this for so many people – all of the guys you came up with, they’re either writing, or directing, or producing, or acting in your films.”
Sandler’s regular directors include Steven Brill, who has helmed five movies and the standup special Adam Sandler: 100% Fresh; Frank Coraci, director of five Sandler pictures; and Peter Segal, who made three Sandler movies in a row between 2003 and 2005.
However, the most profilic Sandler director is Dennis Dugan, who has been the man behind the camera on eight Sandler-starring movies, and one Sandler-produced effort. Fittingly, he has picked up four nominations at the Golden Raspberry Awards for ‘Worst Director’ – all for movies starring the ‘Sandman.’
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