A beloved Adam Sandler comedy nearly cast an Oscar-winning actor, only for Sandler to be hilariously turned down. While Sandler will soon return to his famous role in the upcoming Happy Gilmore 2, Billy Madison remains perhaps the actor’s most popular comedy and a true breakout movie for him.

Sandler embraces his persona of an immature manchild with the story of a spoiled rich adult who must return to complete grades 1 to 12 in order to take over his father’s business. Sandler is hilarious in the lead role, and he is joined by some of his famous friends in smaller roles, including the late comedy legends Chris Farley and Norm MacDonald.

However, the classic Sandler comedy had an interesting bit of casting that didn’t work out. As great as Bradley Whitford was as the scheming villain Eric Gordon in Billy Madison, there were some other notable names, including a future Oscar-winner whom Sandler fought hard to cast.

Adam Sandler Wanted Philip Seymour Hoffman To Star In Billy Madison

Hoffman Ultimately Turned It Down

Adam Sandler revealed on the Fly on the Wall podcast with David Spade and Dana Carvey that his original choice to play Eric was Bob Odenkirk. Odenkirk went on to great acclaim in Better Call Saul and Nobody, but he was only a writer on Saturday Night Live at the times, which helped the studio refuse.

Sandler had to begin auditioning actors for the roles, which is when he came across the audition tape for Philip Seymour Hoffman. While Hoffman went on to become an Oscar winner for his role in Capote and is considered one of the greatest actors of all time, he was still up-and-coming at this time with roles in Scent of a Woman and Nobody’s Fool.

Sandler called the audition “hilarious,” but still had to fight hard with the studio to cast Hoffman. However, once they finally agreed to cast him, Sandler found that Hoffman wasn’t very keen on taking the part, despite auditioning. Sandler recalls their conversation:

“I called him up and said, ‘Hey, it’s Adam,’ and he’s like, ‘Oh hey Adam.’ I go, ‘Hey, I saw your tape, you’re so great, buddy, and they said you don’t want to do it.’ And he goes, ‘Aww, thanks man.’‘So, do you want to do it?’ And he goes, ‘Aww, I can’t.’ And I go, ‘Oh, why not?’ And he goes, ‘Awww… I just don’t want to’… And I go, ‘I really love you.’ And he goes, ‘I know you do,’”

Adam Sandler Eventually Worked With Philip Seymour Hoffman On One Of His Most Acclaimed Movies

They Were Great Together In Punch-Drunk-Love

Despite being turned down for the role, Adam Sandler remembers the conversation with Philip Seymour Hoffman fondly. Luckily, that was not the only chance the two actors had to work together, as they eventually teamed for the first of Sandler’s serious movie roles in Punch-Drunk Love.

While it might be hard to imagine Hoffman appearing in one of those typical Sandler comedies like Billy Madison, it was equally strange for many people to see Sandler appearing in a Paul Thomas Anderson movie with Hoffman. Punch-Drunk Love has Sandler starring as Barry, a socially awkward man who finds love while being blackmailed by a crooked businessman (Hoffman).

Despite having limited interaction in the movie, Sandler and Hoffman are able to go head-to-head as protagonist and antagonist in Punch-Drunk Love after missing the opportunity in Billy Madison. Their fiery phone call and climactic confrontation are highlights of the movie and make us wish they had more opportunities to share the screen.