Adam Sandler once teamed up with veteran actor Winona Ryder for their 2002 flick Mr. Deeds. Throughout the course of the film, Ryder showed Sandler that she could even be funnier than the comic himself at times.
How Winona Ryder showed Adam Sandler that she was funnier than him
Mr. Deeds was a 2002 comedy about an honest and earnest working man who comes to inherit a fortune and a huge media conglomerate. Sandler played the titular character Deeds in the film, with Ryder filling in the role of his co-star. One of the reasons Ryder gravitated towards the feature was simply because she was an admirer of the comedian’s work.
“I’ve always been a fan of Adam Sandler. I’m, like, very strange that way. I can be the biggest snob. Then I realize I’m not a snob at all. One of the things that’s so cool about Adam is he doesn’t do press,” Ryder once told W Magazine.
Sandler had equal words of admiration for his co-star. Ryder managed to win the comic over by proving she was every bit as funny as he was on set. The competition between the two started when the Beetlejuice actor repeatedly told Sandler that she was funnier than him.
“Winona kept leaving messages on my answering machine, boasting, ‘I’m way funnier than you, Adam Sandler, and you’d better recognize it.’ Finally, after the 23rd insult to my comic abilities, I *69ed little Miss HaHa and threw down the gauntlet,” Sandler said.
The two actors would wager which one was funnier by using pizza as the prize.
“‘Winona Ryder, if you think you’re so damn funny, then prove it to me on the silver screen. Me versus you. Mano a mano. The person who receives the most laughs gets a fresh pizza pie of their choice, paid for by the loser,’” Sandler remembered telling Ryder. “Fifty-two days later, after a long, grueling movie shoot, Ms. Ryder happily devoured a large mushroom-and-green-pepper pizza, at my expense. My hat’s off to you, doe eyes. You are one funny diva.”
Why Winona Ryder chose to do ‘Mr. Deeds’ even though she swore off remakes
Mr. Deeds was a remake of the classic 1936 comedy Mr. Deeds Goes to Town. The film was directed by Frank Capra and starred legendary actor Gary Cooper. When Sandler went to remake the film, his goal wasn’t to make a movie that completely mirrored the original. He felt the quality of the classic wasn’t something that could’ve been replicated.
“I loved the original, but I didn’t think I should be redoing a Capra movie. I mean how can you top Capra? Then one day I was talking to my dad and I told him that we were thinking of making an updated version of the film,” Sandler once told Tribute. “He said that was one of my grandma’s favorite movies and that I should do a movie that she would like. That was good enough for me. If my pop tells me to do something, I usually do it. No questions asked!”
Ryder, however, once swore off doing remakes of original works long ago. So when she agreed to star in Mr. Deeds, it raised a few eyebrows.
“That’s the other thing about doing press—if you change your mind, they say, ‘She lied!’ I didn’ t lie, I just changed my mind. But the original Mr. Deeds Goes to Town is a great movie. It is weird to talk about this, because of what has happened in the world since we made the movie—but the reason I wanted to do it was I felt the world needed a family-type movie,” she said.