Leonardo DiCaprio’s Favorite Leonardo DiCaprio Film—and His Biggest Career Regret

Leonardo DiCaprio was five years old when he first appeared on television. 

That was 1979. In 2026, we know him as Arnie Grape in What's Eating Gilbert Grape, Jack Dawson in Titanic, Jordan Belfort in The Wolf of Wall Street, Dom Cobb in Inception, Jay Gatsby in The Great Gatsby…the list goes on! 

The actor is among the most well-known in the entertainment industry, having collected numerous Golden Globe Awards, an Academy Award, a BAFTA, and a SAG Award, along with several nominations. While audiences around the world revisit classics like Titanic and The Wolf of Wall Street, DiCaprio is most fond of his work in a 2004 biographical drama directed by Martin Scorsese. Just as he has films he’s proud to have made, the icon admits there are a few career regrets; one that stands out above the rest.

Here’s a look at Leonardo DiCaprio’s favorite Leonardo DiCaprio film and the role he regrets turning down.

LEONARDO DICAPRIO'S FAVORITE LEONARDO DICAPRIO FILM

In a 2025 conversation with director Paul Thomas Anderson for Esquire, DiCaprio shared that while he doesn’t typically rewatch his own movies, there is one he simply can’t resist replaying from time to time: a film he feels deeply connected to.

"I rarely watch any of my films, but if I’m being honest, there’s one that I have watched more than others. It’s The Aviator. That’s simply because it was such a special moment to me...I was thirty. It was the first time as an actor I got to feel implicitly part of the production, rather than just an actor hired to play a role. I felt responsible in a whole new way. I’ve always felt proud and connected to that film as such a key part of my growing up in this industry and taking on a role of a real collaborator for the first time."

DiCaprio has collaborated with Martin Scorsese, the visionary behind The Aviator, on several major films over the past two decades, including Gangs of New York, The Departed, Shutter Island, The Wolf of Wall Street, and Killers of the Flower Moon.

LEONARDO DICAPRIO'S BIGGEST CAREER REGRET

In the same interview, DiCaprio admitted his career hasn’t been without regrets. He admitted there’s one part he never should have turned down, though he remains happy for the actor who took it and turned it into the “masterpiece” it’s considered.

"My biggest regret is not doing Boogie Nights. It was a profound movie of my generation. I can’t imagine anyone but Mark [Wahlberg] in it. When I finally got to see that movie, I just thought it was a masterpiece."

Mark Wahlberg received Golden Globe and MTV Movie Award nominations for his role as Eddie Adams in the 1997 film, while DiCaprio won an MTV Movie Award for playing Jack Dawson in Titanic, which premiered that same year.

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