‘The Wedding Singer’ Turns 20! Looking Back on Adam Sandler and Drew Barrymore’s First Onscreen Romance

This video is unavailable because we were unable to load a message from our sponsors.

If you are using ad-blocking software, please disable it and reload the page.

Remember when Billy Idol could see what a jerk Glenn was, but Julia couldn’t?

Thankfully, Drew Barrymore’s character came to her senses and The Wedding Singer can now celebrate 20 years since Adam Sandler’s Robbie declared his love for her in the movie’s final moments. Even in a pre-Punch Drunk Love world, it became clear in that moment that the comedian behind Billy Madison, Happy Gilmore, and Opera Man had many layers to spare.

While the movie’s setting was a mere 12 years before its production, it was still more than enough time to examine many of the styles and trends everyone had left behind. Well, most everyone. “You know what's beautiful is, I'm still so out of date anyways that my clothes still match the '85 style,” Sandler told ET on the 1997 set.

“I have to admit. I thought that my Brady wardrobe couldn't have gotten any worse,” said Christine Taylor, who had starred in The Brady Bunch Movie and A Very Brady Sequel before taking the role of Barrymore’s best friend. “Well, little did I know. Welcome to the mid-’80s.”

On his third leading movie, Sandler was about to play the most grounded, level-headed role of his career up to that point. To maintain the standard level of insanity fans had come to expect in his films, Sandler brought out the big guns -- one of them being Steve Buscemi, who gave the best 1-minute-and-52 second-long performance ever put on film. It’s astounding how many funny things were packed into that short window. Even more incredible is how the movie is barely out of the opening credits when this transpires, and somehow the film just gets better after that. Equal parts sweet and side-splitting, The Wedding Singer had an unusually impressive screenwriting braintrust to showcase Sandler’s vulnerable side.

“This is one of the best scripts I've ever read in my whole life. We have Tim Herlihy and Carrie Fisher and Judd Apatow writing it. That's the most brilliant combination you could have for a screenplay,” Barrymore told ET. That’s right: Princess Leia had a hand in writing The Wedding Singer. Among the late Carrie Fisher’s many hats was as a script doctor, which included uncredited work on Hook, Sister Act, and Scream 3. Apatow also lent some jokes to Happy Gilmore, most notably for the movie’s epic Bob Barker fight sequence.

“On Saturday Night Live, we were always trying to come up with a way for me to be a wedding singer,” said Sandler. Having written jokes for Sandler’s stand-up act while they both attending NYU, Herlihy is one of his oldest collaborators and the former SNL head writer has co-scripted 11 movies for the star.

While The Wedding Singer established Sandler as a leading man, the film also marked a pivotal moment in Barrymore’s life and career. Fresh off her infamous performance in Scream, it was a period of reflection for the third-generation actress.

“The other day I was on The Oprah Winfrey Show, actually, and that to me is sort of an epitome of doing something right in your life,” said Barrymore. “And I remember being there and she said, ‘How do you feel about your life?’ And I said, ‘I think my life has become like a fairy tale.’ And I've never thought that before, that I could have a life like that, but I do.” (It’s worth mentioning that Ever After would be released the following summer.)

The Wedding Singer

Drew Barrymore and Adam Sandler in 'The Wedding Singer.'

New Line Cinema

While Sandler has a small circle of frequent big-name co-stars, Barrymore is the only actress who has played his onscreen love interest more than once. After 2002’s 50 First Dates and 2014’s Blended, the two have co-headlined a romantic comedy in each of the last three decades.

When the two sat down with ET in 1998 to promote the movie’s release, they recalled meeting each other for the first time over coffee. “We had a nice time talking about real stuff,” said Sandler. “I knew her for one minute and thought I could tell her everything. Just being with Drew you feel very safe.”

“I always knew that I found him so wonderful and talented. And he writes music and plays instruments and acts and does comedy. He's an incredibly witty person. I was fascinated to get to know him,” said Barrymore.

Performing opposite Sandler turned out to be a dream scenario for her. Having acted since age 6, when she made her screen debut in E.T. the Extra-Terrestrial, Barrymore had been around the industry long enough to appreciate the actor’s enthusiasm and positive attitude throughout the shoot. With microphones and guitars always nearby for the film’s multiple wedding scenes, Sandler was known for keeping momentum up on 12-hour days and making his co-star laugh.

“Drew gets the giggles, and who can tell Drew to stop laughing?” said Sandler. Barrymore added, “It was so nice, because I think the important thing is the experience and to have a wonderful experience. That's what we had.”

As the pair promoted their rom-com Blended in 2014, she described to ET how they’ve remained compatible partners 16 years later.

“We have each other’s back. Always.”



Drew Barrymore Hilariously Recalls Striking Out on Dating Apps -- Watch!

'Charlie's Angels' Reunion! Drew Barrymore and Cameron Diaz Share Sweet Pic Together

Bob Barker Punches His Way onto the Big Screen in 'Happy Gilmore' (Flashback)