Leonardo DiCaprio Then & Now: Photos of the Star When He Was Young to Today

Once a stud, always a stud! Leonardo DiCaprio has grown up before our eyes in Hollywood, and these are the photos of him throughout the years to prove it.

Leonardo DiCaprio’s rise began not on the big screen, but in television commercials. With early ads for Matchbox cars and Kraft Singles, he quickly moved into recurring TV roles — most notably in Parenthood (1990–1991) — before landing his breakout part as Luke Brower on Growing Pains from 1991 to 1992. His critically acclaimed performance in What’s Eating Gilbert Grape (1993) earned him his first Oscar nomination, and his raw turn in The Basketball Diaries (1995) solidified his status as one of Hollywood’s most promising young actors. By the time he starred in Romeo + Juliet(1996) and Titanic (1997), DiCaprio had become a global phenomenon.

Over the next two decades, Leo continued to redefine his career through powerful, complex roles. His ongoing partnership with Martin Scorsese produced acclaimed films like Gangs of New York, The Aviator, The Departed, The Wolf of Wall Street, and most recently Killers of the Flower Moon (2023). He’s also delivered unforgettable performances in Inception, Shutter Island, and The Revenant — which finally earned him his long-awaited Academy Award for Best Actor in 2016.

Now celebrating his 51st birthday on November 11, 2025, DiCaprio shows no signs of slowing down. He recently reunited with director Paul Thomas Anderson for a new film set to begin production in 2026, marking their first collaboration. In an Esquire conversation with Anderson earlier this year, Leo reflected on aging and perspective, saying, “You have a desire to just be more honest and not waste your time. You have to just be much more upfront. It’s almost a responsibility because much more of your life is behind you than it is ahead of you.”

Scroll through to see pics of Leo through the years!

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