The 1995 comedy “Billy Madison” tells the story of dimwitted Billy (Adam Sandler), who is poised to inherit a chain of hotels from his father, Brian (Darren McGavin). However, Brian reveals that while his son was growing up, he had bribed Billy’s school to give him passing grades. Now Billy must prove himself capable of running the business by going back to school and passing all twelve grades within six months. If he fails, the business will go to the hotel’s evil vice president, Eric Gordon.
Initially, Sandler wanted to cast Bob Odenkirk as the villainous Eric, the two having worked together on “SNL.” But Odenkirk, then virtually unknown to movie audiences, was vetoed by studio executives. After an extensive audition session, Sandler fell in love with the performance of a young actor named Philip Seymour Hoffman. However, the executives were reluctant to hire him. Sandler was finally able to convince them, but a new problem arose – Hoffman refused to play the role.
In “Fly on the Wall,” a podcast hosted by David Spade and Dana Carvey, Sandler detailed how he called up Hoffman to see what was going on (via The Playlist). “I go, ‘Hey, I saw your tape, you’re so great, buddy, and they said you don’t want to do it … So, do you want to do it?’” Sandler recalled. “And he goes, ‘Aww, I can’t.’ And I go, ‘Oh, why not?’ And he goes, ‘Aww … I just don’t want to.’”
Fortunately, the role was delightfully filled by “The West Wing” star Bradley Whitford, while Hoffman and Sandler eventually worked together on the film “Punch-Drunk Love.”