Sandler was the brothers' first choice to play Howard Ratner, but it took years for them to reach him. They first attempted in 2011 after they were nominated for an Independent Spirit Award for Daddy Longlegs. No luck. They tried again three years later. "We were told 'he's unavailable during the dates that you need,'" Josh explains. "And we gave a pretty wide window -- it was, like, six months. What about the other six months? And then it was made clear to us that he's just quote 'unavailable.'"
When it seemed like Sandler was indeed impossible to land, the Safdies reached out to other actors. Harvey Keitel was once an option, and they even organized a seder for the Pulp Fiction star and basketball player Amar'e Stoudemire. Then Sacha Baron Cohen became attached, and then Jonah Hill. But it circled back to Sandler after he saw their excellent 2017 heist film Good Time, starring Robert Pattinson.
It does feel like Sandler is the only option for Howard. Not only is he one of the most famous Jewish actors alive, he's also a giant basketball fan, as evidenced by his frequent presence at Knicks games. It wasn't the basketball element that initially drew his attention, however. "I heard more about the diamond stuff. And then I heard about gambling and then I heard about the NBA," he says. "That was great because I do watch the NBA a lot. I love it. When it ended up being Kevin Garnett in the part that was exciting because I knew a lot about Kevin. I watched his whole career."
Sandler, per the Safdies, did have a bit of hesitation. "When Sandler read the character of Howard, there were certain parts of him that he didn't necessarily attach to, or subscribe to. And he was very nervous," Benny says. But the brothers assured him that the process of finding Howard would be a collaboration. Sandler's involvement opened more doors in the Diamond District. The filmmakers started throwing him into "insane scenarios," surrounding him with "with jewelers, bookies, degenerate gamblers" during an early screen test for Fox, who would go on to play Ratner's mistress. The crowd was interested in seeing Sandler, but Sandler wanted to observe the crowd.
"He's kind of doing this hybrid of Sandler and Howard and absorbing [everything] like a sponge," Josh says. Howard is, to put it bluntly, an asshole who tests the limits and patience of everyone around him. "When we would do scenes together and I was being the guy, I could tell in their faces these guys were a little disgusted in me, in their eyes," Sandler says. "They don't say anything. But I was just like, 'Stay committed.'"
Menzel reassures him, "We weren't disgusted." To which Sandler retorts, "You sure?" Stanfield volleys back, "I was."