The Shocking Connection Martin Scorsese, James Cameron And Paul Thomas Anderson's First Oscar Wins Share

The 98th Academy Awards, which we covered extensively on our live-blog, have come and gone, and among the 2026 Oscar winners was beloved director Paul Thomas Anderson for One Battle After Another. With PTA’s win, an Oscar’s connection pops up that actually makes you stop and think. One very specific thing links the first Oscar wins of three wildly different directors: Martin Scorsese, James Cameron, and Paul Thomas Anderson. And no, it’s not a shared genre, a studio, or even a similar style.

All three filmmakers earned their first (and, so far, only) Academy Awards for movies starring Leonardo DiCaprio. Once you see it laid out, it’s hard to ignore. Their connection comes from these movies starring the former teen heartthrob:

• The Departed (Martin Scorsese)
• Titanic (James Cameron)
• One Battle After Another (Paul Thomas Anderson)

Three directors. Three very different careers. One surprisingly consistent through-line. DiCaprio.

The Leo Pattern Is Hard To Ignore

To be clear, these directors are not in the same position regarding their Award wins, though each of them, in my opinion, could be categorized as shocking Oscar wins.

Martin Scorsese famously had to wait decades before winning Best Director for 2007's The Departed, despite building one of the most respected filmographies in cinema history.

James Cameron, on the other hand, didn’t just win for Titanic; he dominated the Oscars with it, which led to his now infamous 'I'm the King of the World' speech. While his other films, like Avatar, have won Academy Awards across his career, his first major breakthrough and the only time he personally took home trophies came with a DiCaprio-led film.

The same goes for Paul Thomas Anderson. After years of critical acclaim and multiple nominations, One Battle After Another finally got him over the finish line, as he won Best Picture, Director and Adapted Screenplay. (Though I would hardly categorize it as one of PTA's best movies.) Like Cameron, his movies have won Oscars (Daniel Day-Lewis won for his performance in There Will Be Blood, for example). However, PTA's personal trophies didn't come to him until he worked with DiCaprio on OBAA.

So while their careers look very different on paper, there’s a strange overlap in how their Oscar stories actually played out.

The Leonardo DiCaprio Factor

What makes this even more ironic is Leo’s own Oscar history. Despite being at the center of these major wins, he only has one Academy Award himself, and it's for The Revenant. And notably, that win has nothing to do with any of the films that helped these directors secure their Oscars.

In other words, the Inception actor has been a key part of multiple Oscar-winning moments for directors, without personally winning for those same projects. That’s kind of wild.

It also says something about the roles he chooses. The Once Upon a Time… In Hollywood lead has built a career around working with filmmakers at pivotal moments, whether that’s helping bring massive projects like Titanic to life or collaborating on prestige films like The Departed and One Battle After Another.

He’s consistently in the mix when something big is happening, even if the awards don’t always land directly in his hands.

It’s easy to write this off as a quirky stat, but it also highlights how certain collaborations shape awards history in ways that aren’t always obvious. DiCaprio has spent years aligning himself with ambitious directors, and those partnerships have clearly paid off, even beyond his own accolades.

Three directors with multiple Oscars between them, and in each case, a Leonardo DiCaprio-led film played a key role in getting them there, especially when it came to that first big win. At the very least, it’s one of those connections that would make an awesome little piece of trivia at your next Oscar night party.

This year's best picture winner and the movie that got Paul Thomas Anderson his first Oscar, One Battle After Another, is streaming with an HBO Max subscription.