It took this hour long conversation with Leonardo DiCaprio at SAG for me to realize that a) I had never really heard the man behind the actor talking at length about his career and craft and b) that I have been following his work since Growing Pains (!) and, without realizing it, have pretty much watched everything he’s done.

DiCaprio has had, very early on, an interesting and unconventional career, focusing first on many indie dramas up until Titanic, that opened him the gates to a whole new sets of projects and filmmakers, and gave him the opportunity to start producing films he was passionate about and needed his name to get green lit.

In this one hour long conversation at the SAG Foundation, DiCaprio looks back at his career and shares about his growth and development as an actor. I think the full session is mandatory -and inspiring- for any active or inspiring actor, but in case life doesn’t give you 1h, here are five highlights:

The 4 Elements to Break Into Hollywood

DiCaprio was born and raised in Los Angeles from New-Yorkers parents but always felt like an outsider as a kid when it came to the Hollwyood System. Even though he lived so close to Hollywood, he admits that he probably wouldn’t have made it if his mother didn’t take his passion and ambition for becoming an actor seriously, and thus didn’t make time to take him to auditions after school. “[Making it] is a combination of being in the right place at the right time, being prepared for it, being aggressive about it, and sticking with it.”

Dealing With Auditions

DiCaprio started as a kid actor and during the auditions, he used to present himself as a jack of all trades, always saying yes to any request from casting directors. After getting only No’s for a full year at around 13, he changed the way he handled the process. “The truth is it was that year of rejection where I suppose I took a different attitude toward the audition process and I started to get jobs after that. And I think it was really because I said to myself: I’m not dependent on this job. This isn’t gonna define me. I started to sell myself less, prepare more for the roles, really investigate the characters as much as I could and not feel like my self-worth was dependent on whether I booked the job or not. And I think that what clicked with me and I started realizing that casting directors weren’t necessarily looking for the broadway showmen that could do whatever they wanted but somebody that had a different attitude about the audition process. Because you know, you focus more on the work, you focus more on the character rather than selling yourself constantly to these people.”

Learning the Rope of the Job

DiCaprio’s break through role came with his This Boy’s Life performance against Robert De Niro, a role he won over 400 other kids during casting sessions. That was his first experience on a film set and one that set the foundations of his life as an actor. “I’m the most nostalgic about that movie and I remember every single day on set because everything was so new to me. Having come straight from a Sitcom where everything was very relaxed on set, everyone was constantly joking around to having De Niro walk on set and the difference, the sort of dynamic and presence that he had wit the crew, I was just like “What is going on here? I don’t quite fathom why is everyone so serious about?” And then I started to see his process, the improv, just the technical work was something that I witnessed every single day and really blew me away. Because I didn’t know how to conduct myself on a set, I was just sort of a wild animal and it was really Michael Caton-Jones that gave me some of these incredible fundamentals about making a movie. You know every time I would sort of get tired of a scene or not want to persist, he’d go “Pain is temporary, Film is forever. You go back in there and you give it everything you possibly can.“

About His Collaboration with Martin Scorsese

“The truth is, we work well together. I think we are different generations but we share similar taste in materials and the type of movies that we want to do, and I think accidentally after The Aviator things have come together simultaneously or we’ve developed things together and I suppose I’ve been convincing a few times with him and persuading him to do certain materials because I just felt there was nobody else for the job.”

DiCaprio doesn’t say this lightly as the Wolf of Wall Street took 7 years to get made, after Scorsese decided to opt-out of it few years ago, seeing the Studios wouldn’t give them the financing and freedom he wanted to have on his films. The movie kept being pushed by the Studios, but DiCaprio couldn’t convince himself doing it with anyone else but Scorsese, and waited until they finally gained full creative freedom to make it happen.

Scorsese’s Best Advice

While shooting the Wolf of Wall Street, a film pretty much filled with characters with zero moral compasses, Martin Scorsese gave an advice to Leonardo DiCaprio that rang true, he said: “Look Leo, I’ve done many films in my life and I have to say, as long as you’re honest and authentic in your portrayal of who these people are, no matter how despicable at times, no matter what part of the darker nature of humanity you’re exploring, audiences will always connect with that, and go along with that journey with you. And that’s what I found in my career.”

On that inspiring note, I let you enjoy the full conversation:

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