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Young Leonardo DiCaprio Pictures

These Pictures of Leonardo DiCaprio at Peak Teen Heartthrob Status Are a Major Trip

Mar 8 2019

You may find this hard to believe, but Leonardo DiCaprio wasn't born sexy. When he first appeared on the scene in the late '80s, Leo was just a baby-faced tween with adorably floppy hair and a sweet smile, almost unrecognisable from the superhottie he is now. From his first big supporting role in What's Eating Gilbert Grape to his starring roles in the megapopular flicks Romeo + Juliet and Titanic, little Leo definitely has come a long way. Read on to see what the now-44-year-old actor looked like when he first started his career as a fresh-faced 15-year-old.


Image Source: Getty / Barry King

1989

15-year-old Leonardo DiCaprio was the epitome of late '80s fashion when he attended the TJ Martell Music Event in 1989.

Image Source: Getty / Jeff Kravitz

1992

Nearly three years later at the 1992 MTV Rock 'n' Jock Basketball event at Bren Centre in Irvine, CA, little Leo looked as though he'd barely aged a day.

Image Source: Getty / Jeff Kravitz

1993

Leo was all smiles at the What's Eating Gilbert Grape premiere in 1993, which was the film that earned him his first Academy Award nomination.

Image Source: Getty / Terry McGinnis

1993

A more serious and stylist Leo attended the This Boy's Life premiere that same year, a movie in which he had his first starring role.

Image Source: Getty / Barry King

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1993

His adorably floppy hair at the Benny & Joon premiere in Los Angeles was everything.

Image Source: Getty / Barry King

1993

And if he hadn't already, Leo officially earned '90s hair royalty status at the Carlito's Way premiere.

Image Source: Getty / Barry King

1994

By the time the 51st Annual Golden Globe Awards rolled around in January of 1994, a brooding 19-year-old Leo was starting to look less like a boy and more like a man.

Image Source: Getty / Terry McGinnis

1994

When he wore a tux to the 66th Annual Academy Awards at Dorothy Chandler Pavillion in Los Angeles, he melted our hearts.

Image Source: Getty / Barry King

1994

Just look at those baby blues during this close-up shot from the Red Rock West party at Club USA in New York!

Image Source: Getty / Steve Eichner

1994

Leo looked sweet as can be during the D.A.R.E. Benefit at Smashbox Studios in Culver City, CA, in 1994.

Image Source: Getty / Barry King

1995

And even though he probably should have gotten his hair trimmed before The Basketball Diaries' premiere in Westwood, CA, we still loved him.

Image Source: Getty / Steve Grantiz

1996

Romeo + Juliet rocketed Leo to superstardom, and he definitely dressed accordingly at the film's 1996 premiere in Los Angeles.

Image Source: Getty / Barry King

1996

Those are definitely the coloured lenses of a superstar.

Image Source: Getty / Fred Duval

1997

If Romeo + Juliet didn't put Leo on your radar, then he was impossible to ignore after Titanic, which premiered at Mann Chinese Theatre in Los Angeles in 1997.

Image Source: Getty / Steven Granitz

1998

By the time The Man in the Iron Mask premiered at Ziegfeld Theatre in New York, there was almost no trace of Leo's baby face left.

Image Source: Getty / Kevin Mazur

2000

And finally, when The Beach premiered at Mann Chinese Theatre in 2000, Leo had fully blossomed from cutie-pie child star to certified hunk.

Image Source: Getty / Steve Granitz

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