The Director of ‘The Wedding Singer’ on Turning Adam Sandler into a Rom-Com Star

His Meet Cute with Sandler

I first met Adam Sandler when I was a freshman at NYU. Adam was in my dorm, and he would do comedy shows. One night, my roommate (future Happy Madison Productions co-founder) Jack Giarraputo was like, “Let’s go hang out with Adam and (future screenwriter) Tim Herlihy.” We ended up having such a fun night, then we came back and hung out in the dorm and probably smoked weed. We made each other laugh all night.

That was toward the end of freshman year, and we made sure we lived next to them in the dorm the year after that. We ended up being buddies all through college. We’d go see Adam’s stand-up. We’d write songs together. We used to do a show in the dorm called Adam Sandler and the Four Skins — I was one of the Four Skins.

Back then, we talked about doing movies together, but when Adam did Happy Gilmore, I hadn’t directed a movie yet so it was too early on. When The Wedding Singer came around, though, I had already done a movie so it was timed perfectly. In 1995, Adam was in L.A. working on his second comedy album, What the Hell Happened to Me?, and he told me to come out there to help him with it. I wrote on a bunch of those tracks, and I directed the music video for “Steve Polychronopolous,” which was kind of a precursor to The Wedding Singer because the guy was a 1980s guy who wore stonewash jeans and had a bi-level haircut.

The album went double platinum, and Adam did a rock-and-roll tour after that. I did the visuals on the tour, which included a bunch of videos onstage. One of the skits from that was about a talking goat that became a stoner classic. For our final date in Los Angeles, the head of New Line saw the show and said, “I want you guys to do the goat movie.” We said, “That’s awesome, but we think Adam’s ready for a romantic comedy.”

Writing ‘The Wedding Singer’

Adam and Tim had the idea for a movie about a wedding singer who gets his heart broken, but then has to go back and do weddings. I was also pushing for the idea of an 1980s movie. We pitched the idea to New Line, and they loved it.

It took about a year to write the script. Tim and Adam wrote a draft and it was funny, but it needed more of a feminine touch to it, so we hired Carrie Fisher, who was known for writing romantic comedies like When Harry Met Sally. She was so funny and brilliant. I spent almost every day with her for six months. She liked to sit in bed; so me, her and Jack Giarraputo would sit in bed, watch old movies and work on the script. 

Through that, we layered in a lot of the heart for The Wedding Singer. For example, the scene I’m probably most proud of came out of watching old movies with Carrie Fisher. One thing I realized about romantic comedies is that a lot of the greats have a near-miss moment between the two leads. For us, it’s when Robbie Hart is going to tell Julia he loves her. That’s while she’s saying “Julia Gulia” in the mirror, and it makes her cry. Then she starts saying “Mrs. Robbie Hart” instead, and she starts smiling.

Unfortunately, that’s when Robbie catches her and she looks happy, so he decides not to tell her how he feels. There’s this beautiful shot of her through the window, practicing saying Robbie’s name, but he doesn’t know that. It’s one of those moments that you’re dying for them to be together. 

In that scene, Robbie is rehearsing to himself what he’s going to say to Julia, and at first, Adam was a little skeptical about it, fearing it was a little too “typical romantic comedy.” That ended up working for that scene, but there were other aspects we ended up dialing back. Adam was always very smart about pleasing his fanbase, and there was some worry from him about alienating his fans with this movie. But we found a happy medium. When you’re making a movie, it starts to find its own soul, and you have to be true to whatever that is. 

Casting Drew Barrymore

New Line had a movie they owed to Drew Barrymore, so they mentioned her for Julia. The minute we met her, we knew she’d be great. She’s so accessible. She oozes love and goodness, and she was a perfect leading lady to play opposite Adam. A romantic comedy works on believing the two people should be together, and Adam and Drew’s on- and off-screen chemistry made you really want them to be together.

Shooting ‘The Wedding Singer’

It was really a low-budget movie, and I had to shoot it in 34 days. We shot it all in Los Angeles, but we found places that looked like back East. It was cool to see Adam’s acting in that movie because sometimes Adam likes to be Adam in a movie, and other times he becomes a different person. In The Wedding Singer, he became Robbie Hart. 

The Sounds of ‘The Wedding Singer’

“Love Stinks.” It was fun to see Robbie, who’s this sweet guy, get angry, and “Love Stinks” was the perfect song to do that with. It was a chance for Adam to tap into the Happy Gilmore sound a little bit. Plus, all that stuff with “Table Nine” was really funny. I heard that became a thing at weddings afterward — that Table Nine was the loser table.

“Somebody Kill Me Please.” I was a big Cure fan, and Sandler loves The Cure because of me — that’s the sound we were going for with “Somebody Kill Me Please.” It was Adam’s idea that Robbie wrote half the song when he and his ex were still together and the other half after they’d broken up. Also, for a PG-13 movie, you only get one “fuck,” so we’d always try to save it for the perfect place. We knew it was going to go here.

“Rapper’s Delight.” Ellen Dow was a no-brainer when we were casting the role of Rosie — she was so sweet and so funny. We were, though, having a bit of trouble with her singing “Rapper’s Delight.” I knew she had it in her, but she just couldn’t get through it. It wasn’t until I told her to dance while she was singing it that she finally got it down. It was such a stroke of genius to put that moment in the trailer because I think that was part of the reason why we did so well on opening night. You’re always a little afraid to put one of your biggest jokes in the trailer, but it worked here and it was still funny when you saw it in the movie. 

“I Wanna Grow Old With You.” The concept of “growing old with you” was there early on in the movie, and Sandler took that and wrote this amazing song for the end. The magic in that scene really comes from Drew. I made sure she didn’t hear the song until we shot her angle, so those tears are real tears. I think she really fell in love with the character of Robbie Hart as he sang to her. 

Getting Billy Idol

We were trying to think of who would be a good rock star to see on the plane at the end. We thought of Eddie Van Halen, but he said he wasn’t good on camera. Then we all thought Billy Idol would be perfect, and it turned out his son was a big Adam Sandler fan. That guy was so cool and funny and charismatic. I remember I told him, “I used to dress like you to get girls,” and he said to me, “I used to dress like me to get girls!” 

Opening Night

Now they have metrics for this kind of thing, but back then you didn’t know what a movie was going to open at. So, me, Drew, Adam, Jack and Tim flew to New York, rented a bus and went theater to theater in Manhattan. We’d ask if we could peek our heads in, and we were told things like, “All four screens are sold out.” It was this surreal dream.

We were able to duck into a few screenings, stand in the back and see people laughing their asses off. It was far beyond our expectations and the start of Adam and I making a bunch more movies together — just like we said we’d do in college. I’m amazed that people are still watching The Wedding Singer 25 years later. It may not have any awards or anything, but that’s the ultimate reward as a filmmaker — to turn the TV on and still see your work playing.