What's Leonardo DiCaprio's Biggest Career Regret?

I think it's pretty indisputable that the last movie star working right now is Leonardo DiCaprio. There are a few names in contention from the younger generation (look at you, Chalamet), but DiCaprio is the gold standard for which we'll measure all of them.

And you don't get to be in the upper echelons of that kind of career by just taking crappy roles; you have to be selective.

But not every choice you make is perfect. We just looked at how Denzel Washington passed on Se7en. If you're going to be successful, you have to take risks, be okay with falling, and then bounce back on the other side.

So, it's no surprise that a guy like Leonardo DiCaprio has a role he passed on — but wishes he hadn't.

In a recent interview in Esquire Magazine, where DiCaprio talks to Paul Thomas Anderson about their upcoming film, One Battle After Another, DiCaprio says he wishes he hadn't turned down a role in this PTA classic.

DiCaprio expanded, "I’ll say it even though you’re here: 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. It’s ironic that you’re the person asking that question, but it’s true."

Well, the two of them are finally working together on this new movie, and it looks like it's going to be another wild ride.

DiCaprio picked to be in this movie for a very simple reason: "I know One Battle After Another has been on your desk for a long time. It was a personal story for you in a lot of ways and certainly pertinent to the world that we’re living in right now. But ultimately, wanting to do this movie was pretty simple: I’ve been wanting to work with you—Paul—for something like twenty years now, and I loved this idea of the washed-up revolutionary trying to erase his past and disappear and try and live some sort of normal life raising his daughter."

I love that DiCaprio has a regret of not being in a PTA movie, so you knew he wasn't going to pass on another one. He's a guy who likes to correct these past visions and ideas and always picks forward-thinking roles.

In the interview, both of them unpack who they are as artists, and I like the idea of a filmmaker and his actors working in concert to think not only what this movie is about, but what each of them can bring to the process that informs the choices on the screen.

That was a lesson DiCaprio learned when he was 30 and trying to pick his next role. He tells the story as he reflects on his past movies, and the only one he watches over and over.

DiCaprio says, " 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 had worked with Marty [Scorsese] on Gangs of New York, and I’d been toting around a book on Howard Hughes for ten years. I almost did it with Michael Mann, but there was a conflict, and I ended up bringing it to Marty. 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 learned how to be a star and how to write his own fortune at such a young age, and that's helped him pick roles moving forward and to sustain the mythos of just being a movie star.

If he's in a film, I stop to watch it.

And I cannot wait to see what he brings to the table in this newest venture.

Let me know what you think in the comments.