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It’s hard to believe it’s been 16 years since the world first swooned over heartthrob Jack in the blockbuster hit Titanic.

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But those 16 years haven’t passed in vain. Since then, Leonardo DiCaprio has starred in a number of headlining roles that have catapulted him to new levels of acting stardom, but it didn’t come without levels of insecurity.

The single 38-year-old actor is the selected face for the cover of the May issue of Esquire and in the corresponding interview, he opened up about the pressure that comes with such a high level of fame. 

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Leo suited up for the cover and the spread that served as a reminder that even though he’s left the role of Jack in the past, he still has the ability to steal some hearts. 

Check out some excerpts from the interview below. 

On being single: 

“Six months of being on location or being off in Morocco or someplace like that is not the best thing for a relationship.”

On what propels him: 

“I always thought of myself as the underdog, because I didn’t have nice enough clothes or maybe my hair didn’t look good. And so you have to understand – getting your foot in the door is like winning the lottery. It’s literally like winning the lottery if you get to have a career. And I’ve always felt, Okay, now I’ve gotten this shot, and I’m lucky to have gotten this shot, and if I don’t do this to the best of my ability – if I don’t work my as* off and make a life of it – I’ve squandered this incredibly golden opportunity. And that’s always been what has propelled me.”

On his early success: 

“I really didn’t understand what fame was and I didn’t understand what being in a giant hit was and I didn’t understand what a giant hit Titanic was compared to other giant hits. There was no rule book. There was nobody to navigate me through the experience of being watched all the time and nobody to tell me how to be normal when everybody is acting and looking at me differently.”

Be sure to check out the full interview over at Esquire magazine.