Believe it or not, there was a time when Adam Sandler wasn’t the king of Netflix or the guy who could get a $200 million comedy greenlit with a single phone call. Long before he was Billy Madison or Happy Gilmore, he was just a 22-year-old kid from NYU with a weird haircut and a dream of not being a waiter anymore. But here’s the kicker: his first foray into cinema wasn't a hit. It wasn't even "good" by most conventional standards.
The Adam Sandler first movie is a bizarre, low-budget fever dream titled Going Overboard. Released (if you can call it that) in 1989, it’s a film that feels like it was made by people who had never seen a movie before, yet somehow had access to a cruise ship.
Most fans think Sandler’s career started on Saturday Night Live. It didn't. He had already starred in a feature film before Dennis Miller ever spotted him at a comedy club. Going Overboard is that "skeleton in the closet" that every superstar has. It's awkward. It's messy. Honestly, it's kinda fascinating to watch now just to see how much of the "Sandler persona" was already there, even if the jokes were landing with a thud.
The Cruise Ship Comedy That Almost Sank a Career
The plot of Going Overboard is basically a thin excuse for a bunch of weird sketches. Sandler plays Schecky Moskowitz. Schecky is a struggling comedian working as a waiter on a cruise ship. He's desperate for a shot at the stage, which is currently occupied by an insult comic named Dickie Diamond.
When Dickie gets locked in a bathroom, Schecky gets his big break.
The movie isn't just a straightforward story, though. It uses this meta-narrative where a General (played by Burt Young of Rocky fame) is watching the movie on a VHS tape. He stops the tape, talks to the camera, and eventually sends terrorists to the ship because he's offended by Miss Australia. Yes, terrorists. In a cruise ship comedy.
✨ Don't miss: Henry Golding in Crazy Rich Asians: What Most People Get Wrong
Why the production was a total mess
The backstory of how this thing got made is almost funnier than the movie itself. The crew basically "stole" the production value by filming on a real cruise ship heading to the Miss Universe pageant.
- The Budget: They had about $200,000. In movie terms, that’s basically lunch money.
- The Lenses: Legend has it the camera crew actually forgot a box of lenses at the dock. The cinematographer had to shoot the whole movie with whatever was left, which explains why some shots look... off.
- The Cast: This is the wildest part. Along with Sandler, you've got Billy Zane playing King Neptune (who appears in a vision to give Schecky advice), and a very young, very skinny Billy Bob Thornton as a heckler. Even the legendary Milton Berle shows up as himself to give Sandler a pep talk.
Imagine being 22 and filming a scene with Milton Berle on a boat in the middle of the ocean. Sandler has actually said in interviews that meeting Berle was the highlight of the whole experience. He didn't care that the movie was a disaster; he was just stoked to be an actor.
Going Overboard: What Most People Get Wrong
People often assume this was a big theatrical release that flopped. Not really. It barely existed until Sandler became a massive star in the mid-90s. Once Billy Madison and Happy Gilmore took off, video rental stores were desperate for anything with Sandler's face on the cover.
That’s when Going Overboard was re-released on VHS. If you saw it in the 90s, you probably felt tricked. The cover art usually featured a much older, "famous" Adam Sandler, but the movie inside was a grainy, low-res relic from 1989.
Is it actually watchable?
If you're a die-hard fan, yeah. It’s a time capsule. You can see the beginnings of his "mumbling but loud" delivery. You see his loyalty to his friends starting early, too—Allen Covert, who is in almost every Happy Madison movie today, is in this.
✨ Don't miss: Why Never Let Her Slip Away Still Hits Different Decades Later
But if you’re looking for The Wedding Singer levels of charm, stay away. The jokes are mostly "anti-comedy" before that was a cool thing. Schecky’s stand-up routine is intentionally bad, which is a risky move when the movie surrounding it isn't exactly a masterpiece either.
The Pivot to SNL and Beyond
After the Adam Sandler first movie failed to make him a star, he went back to the grind. He was doing stand-up in Los Angeles when Dennis Miller saw him. Miller told Lorne Michaels, "You gotta hire this kid."
Sandler started at SNL as a writer in 1990. He wasn't even supposed to be on camera much. But then "Opera Man" happened. Then "The Thanksgiving Song" happened. By 1991, he was a cast member. By 1995, he was a movie star.
It's a testament to his work ethic. Most people would have crawled into a hole after their film debut featured a scene where they talk to a hallucination of Billy Zane in a fish suit. Sandler just kept moving.
Actionable Insights for Film Buffs and Fans
If you're planning to track down Going Overboard, here is how to handle it:
- Lower your expectations. Don't go in expecting Uncut Gems. Go in expecting a high school theater project with a slightly better budget.
- Watch the cameos. Seeing Billy Bob Thornton and Billy Zane before they were household names is the best part of the experience.
- Look for the "Sandler-isms." Notice how he breaks the fourth wall. He still does that today, just with much better lighting.
- Check the credits. You'll see names that still work with him today. It’s a masterclass in how to build a "crew" that stays with you for forty years.
Ultimately, Going Overboard isn't a "good" movie, but it is a necessary one. It’s the proof that everyone starts somewhere. Even the guy who eventually signed a quarter-billion-dollar deal with Netflix once had to wear a Speedo and tell bad jokes on a boat to get his foot in the door.
To really understand the trajectory of a comedy icon, you have to see the failures. You have to see the moments where the "voice" wasn't quite found yet. That’s what this movie provides. It's a 99-minute reminder that persistence usually beats a perfect start.