If you look at the landscape of Hollywood today, it's pretty weird to realize that two of the biggest titans in cinema history—Johnny Depp and Leonardo DiCaprio—only ever shared the screen once. Just one time. It happened in 1993, long before the Jack Sparrow eyeliner or the Oscar-chasing intensity of The Revenant.
The movie was What’s Eating Gilbert Grape.
Honestly, it’s a bit of a miracle the film even exists in the way it does. You have a 29-year-old Depp, who was already a bit of an indie darling thanks to Tim Burton, playing the "straight man" to a then-unknown 19-year-old kid named Leo. At the time, nobody knew DiCaprio was going to become DiCaprio. They just saw a scrawny teenager who was so convincing as the intellectually disabled Arnie Grape that some audiences actually thought the production had cast a non-actor for the part.
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Why the collaboration was so tense
It wasn't all sunshine and brotherly love on that Texas set. Johnny Depp has been pretty open about the fact that he was "torturing" Leo during filming.
Depp was going through a dark patch personally. He was moody. He was tired. And here comes this 19-year-old kid, full of more energy than a golden retriever, constantly talking about video games. Depp famously admitted at the Santa Barbara International Film Festival years later that he’d lose patience with him. Leo would try to sneak a drag of Depp's cigarette while hiding from his mom, and Depp would just shut him down.
"No, I will not give you a drag from my cigarette while you hide from your mother again, Leo," he’d tell him.
It sounds harsh, but that friction actually served the movie. In What's Eating Gilbert Grape, the relationship between the brothers is defined by a deep, weary love buried under layers of frustration. Gilbert (Depp) is trapped. He’s the caretaker for Arnie and their morbidly obese mother, Bonnie. He’s a guy whose life is on a permanent "pause" button while everyone else moves on. That genuine irritation Depp felt toward the energetic kid on set translated perfectly into Gilbert’s quiet desperation.
The casting drama you probably didn't know
Here is a wild bit of trivia: Leonardo DiCaprio almost didn't get the role.
The producers were looking at several young actors, including Corey Feldman. Yeah, the Goonies star. Feldman has since claimed that Depp was the one who pushed him out of the running, but most film historians point to director Lasse Hallström’s realization that DiCaprio was simply "the one."
Leo went deep for this. He spent time at a home for mentally ill teens in Austin, researching mannerisms and speech patterns. He didn't want to do a caricature. He wanted to make Arnie human. When you watch the film now, his performance is the thing that still hits the hardest. It’s messy. It’s loud. It’s incredibly vulnerable. It earned him his first-ever Academy Award nomination, and honestly, he probably should have won.
A one-and-done legacy
People always ask why there isn't another Johnny Depp and Leonardo DiCaprio movie.
The short answer? Career trajectories.
- Depp leaned hard into character acting and blockbusters (Pirates, Alice in Wonderland).
- DiCaprio became the king of the prestige drama, working almost exclusively with directors like Scorsese and Tarantino.
They became two different kinds of stars. Depp became a brand; Leo became a genre.
But What’s Eating Gilbert Grape remains this weird, beautiful time capsule. It’s a movie about the weight of family and the suffocating nature of small-town life. It’s also a reminder that before they were the faces of billion-dollar franchises, they were just two actors in the dirt of Manor, Texas, trying to figure out how to be brothers.
There’s a spot in Manor, Texas, on E Parsons Street, where Johnny Depp actually signed his name and left a footprint in wet concrete during filming. It’s still there. It’s a literal mark of a time when the biggest movie stars in the world were just a couple of guys in flannel shirts wondering what was next.
What you should do next
If you haven't seen the film in a decade, go back and watch the scene where Gilbert finally snaps and strikes Arnie. It’s one of the most heartbreaking moments in 90s cinema because you can see the exact moment the "knight in shimmering armor" cracks.
To truly appreciate the evolution of Johnny Depp and Leonardo DiCaprio, follow this viewing order:
- Watch What's Eating Gilbert Grape (1993) to see the raw, unrefined talent.
- Move to Donnie Brasco (1997) to see Depp at his absolute peak of subtle, dramatic acting.
- Finish with The Aviator (2004) to see the moment DiCaprio fully transitioned from a "teen idol" into a powerhouse lead.
The contrast between their 1993 performances and their later work tells the entire story of modern Hollywood.