How Many Movies Have Adam Sandler And Drew Barrymore Made Together?

Adam Sandler and Drew Barrymore's on-screen chemistry has taken over the big screen on multiple occasions over the course of their respective acting careers. The first film they starred in together, "The Wedding Singer," was released back in 1998. Their collaboration for the film was a massive box office success, grossing over $80 million in the United States and Canada alone, per Rotten Tomatoes. 

The film's director, Frank Coraci, knew it was going to be special from the beginning, but didn't anticipate just how successful it would be. On the 20th anniversary of "The Wedding Singer," Coraci told E! News that he noticed Barrymore and Sandler's chemistry "right away." He added, "That's what I think, for me, made the movie really amazing. There were so many moments to it, but the fact that they bonded like friends is what made you believe...that [Robbie and Julia] falling in love is legitimate."

Prior to acting together in "The Wedding Singer," Barrymore had a feeling that they would work well together, and even pitched Sandler the film in hopes he would agree to star in it. In an interview with Entertainment Tonight, she revealed, "I was just trying to convince him of my plot, because I was scheming. I was a scheming MacPherson because I knew we were supposed to partner up." Thankfully for moviegoers, "The Wedding Singer' was only the beginning of Sandler and Barrymore's journey as collaborators and long-term friends.

Following the massive success that came from "The Wedding Singer," Drew Barrymore and Adam Sandler decided to team up again for the 2004 blockbuster hit "50 First Dates." The film did exceedingly better than "The Wedding Singer" and grossed $120 million in the United States and Canada alone. According to The Guardian, Sandler asked Barrymore to star in the film as his love interest, as well as co-produce it with him. The film follows the life of Barrymore's character, Lucy, who suffers from short-term memory loss after getting into a car accident. Lucy lives the same day over and over again as Sandler's character, Henry, attempts to swoon her every day because she is incapable of remembering him.

In 2020, the actors did a short mock sketch of "50 First Dates" on Barrymore's morning talk show, "The Drew Barrymore Show," and Sandler poked fun at catching Barrymore up on the new way of living during the pandemic. After the sketch, Sandler shared some touching words regarding his friend's success and new show. "I could honestly not be more excited for you. You have your own show now," Sander said (via Entertainment Tonight). "You are going to make people so happy every day, every time they see you. You are magic."

Luckily, "50 First Dates" did not mark the end of Sandler and Barrymore's journey as collaborators and in 2014, they returned to the big screen together.

Drew Barrymore and Adam Sandler reunited a third time for the 2014 film "Blended." While promoting "Blended," Sandler opened up in an interview with Collider about his friendship and working relationship with Barrymore. "We've always stayed in touch and we've always been good friends. We check in on each other, as much as possible," Sandler said. "No matter what's going on, I'm always pulling for Drew, and she's the same way, whenever I'm doing something. I know she's pulling for me. We just have a nice friendship."

The duo was definitely happy with their performances in "Blended," despite mixed reviews from critics. In an interview with ABC, Barrymore told Sandler, "I love you in this movie." She added, "You are so good. There's so many versions of things I love about you in this movie. I told you, you're like a quilt in this movie." In terms of how their friendship has evolved over the past two decades, Barrymore revealed, "We've like grown up together. When we did 'The Wedding Singer,' life was different. When we did '50 First Dates,' life was different."

Sandler and Barrymore now both have families of their own, but have remained committed to their craft over the past several years. And judging by their collaboration history, they're due for a reunion on the big screen very soon.