The role Quentin Tarantino wrote for Adam Sandler

Scheduling conflicts can be a cruel mistress, especially when it robs audiences of the chance to see Adam Sandler starring in a Quentin Tarantino movie, something that’s never going to happen now unless the filmmaker decides to cast the resurgent star in his upcoming tenth and final feature The Movie Critic.

Tarantino has developed a reputation for taking popular stars and deliberately casting them against type, a recurring theme throughout his career that resuscitated John Travolta post-Pulp Fiction, let Kurt Russell ham it up as a serial killer in Death Proof, and allowed Leonardo DiCaprio to break bad as a villain in Django Unchained, to name just three prominent examples.

As for Sandler, he’s made a habit of offering fitful reminders that he’s a tremendously talented dramatic actor, albeit one that had gotten far too comfortable staying firmly in the wheelhouse of churning out a string of forgettable comedies with his friends. There’s been a shift in that regard recently, though, but that was far from being the case a decade and a half ago when Inglourious Basterds was coming together.

Tarantino and Sandler were already friends by that point, but despite writing a character in the revisionist World War II epic specifically for the Happy Madison Productions founder, another one of his regular cohorts swooped in to get there first, ruling the star out of becoming part of the titular Nazi-hunting brigade.

When Tarantino was prepping Inglourious Basterds, Judd Apatow was putting the pieces together for Funny People, with Sandler committed to the latter, something the comedy powerhouse regretted in retrospect. “I feel bad because when I did Funny People with Sandler, I wasn’t aware that that was the exact time you were trying to use him for Inglorious Basterds,” he said on Bill Maher’s Club Random podcast.

Tarantino admitted that he’d been toying with the idea of casting Sandler as Donnie Donowitz for almost a decade at that point when the pair co-starred in Little Nicky. “I wrote the Bear Jew for Adam Sandler. When I was doing Little Nicky, he’s telling me like, ‘Oh man, I get to fucking beat up Nazis with a bat? Fucking great! Fucking awesome! I can’t fucking wait! I can’t fucking wait,'” he said. “He was like telling every Jewish guy, ‘I’m going to fucking play this guy who beats up Nazis with a fucking bat.’”

Some things just aren’t meant to be, with Tarantino drafting in his buddy and fellow filmmaker Eli Roth to play the role instead. Most folks would agree that his performance as Donowitz is far from being a highlight of Inglorious Basterds, something that wouldn’t have been true of seeing Sandler collaborate with one of Hollywood’s most exciting directors on a blood-soaked wartime thriller.

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