Now one of Hollywood’s most recognisable A-listers, Leonardo DiCaprio rose to prominence in the early 1990s as one of America’s most promising young talents following several spellbinding performances. In 1993, DiCaprio drew crucial attention with two breakout roles: This Boy’s Life, his first role alongside Robert De Niro, and What’s Eating Gilbert Grape, his first and only collaboration with Johnny Depp.

For a comical and deeply moving portrayal of Gilbert Grape’s mentally disabled brother, Arnie, DiCaprio earned his first Oscar nomination. Although fans were hopeful on the evening of the awards ceremony in 1994, the 19-year-old lost his ‘Best Supporting Actor’ nod to the more experienced Tommy Lee Jones, who gave a similarly impressive performance in Andrew Davis’ The Fugitive.

In 2016, DiCaprio finally won his first Academy Award. The ‘Best Actor’ trophy was presented for the star’s gripping lead role as Hugh Glass in Alejandro González Iñárritu’s The Revenant. Just a few months before his win, Time Out asked the actor what an Oscar win would mean to him.

“Honestly? It’s never ever what I’m thinking about when I’m making movies,” he said. “There’s nothing I’ve done for the specific reason of getting an award. Every single time, you just go in there trying to bat a thousand, trying to give it your all.”

With the conversation moving onto his missed chance in 1994, DiCaprio was asked whether he had an acceptance speech prepared after What’s Eating Gilbert Grape. “No! I had absolutely nothing prepared,” he asserted. “I didn’t think there was a shot in hell I’d get it. It would have been an absolute catastrophe if I had.”

Throughout his innumerable interviews over the past three decades, DiCaprio has never failed to convey a humbleness foreign to the Hollywood stereotype. When he accepted his Oscar in 2016, the actor was sure to mention climate change, a cause close to his heart: “I thank you all for this amazing award tonight. Let us not take this planet for granted. I do not take tonight for granted. Thank you so very much.”

Of course, DiCaprio’s humbleness isn’t entirely foreign to the showbiz elite. Off the top of my head, Keanu Reeves’ legacy as the ultimate “nice guy” is only just outweighed by his acting and musical exploits. As for DiCaprio, his humility stems from an ordinary working-class background and high-grade parenting.

In the same Time Out feature, the interviewer referenced DiCaprio’s childhood in a “tough part of LA” when asking whether he still feels like an “outsider” in Hollywood. “Do you ever still feel like that?” DiCaprio said, repeating the question, answering, “I think I will always feel like an outsider”.

To explain his point, DiCaprio mentioned one of his closest confidantes, filmmaking hero Martin Scorsese. “Marty was the same,” he pointed out. “He came from the streets of New York and didn’t feel like he belonged in Hollywood. I can remember getting rejected systematically by casting directors as a young kid. I felt like the biggest outsider there ever was, that I’d never belong in that club. I had this idea that one day they reach out, bless you and say: ‘You are now part of this elite. You are the chosen one.’”

As to whether DiCaprio feels blessed now, he said, “Hell yeah!”

DiCaprio may always feel bound to the streets from which he came, but they are a vital part of his story and helped shape him into the grounded individual his fans appreciate today. Hollywood may never have extended a branch in rough waters, but DiCaprio’s talent and graft saw to it that the cream rose to the top.

Watch Leonardo DiCaprio’s Academy Award acceptance speech below.