You may find this hard to believe, but Leonardo DiCaprio [1] 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 [2] 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 [3], 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.
1989
15-year-old Leonardo DiCaprio [5] was the epitome of late '80s fashion when he attended the TJ Martell Music Event in 1989.
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.
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.
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.
1993
His adorably floppy hair at the Benny & Joon premiere in Los Angeles was everything.
1993
And if he hadn't already, Leo officially earned '90s hair royalty status at the Carlito's Way premiere.
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.
1994
When he wore a tux to the 66th Annual Academy Awards at Dorothy Chandler Pavillion in Los Angeles, he melted our hearts.
1994
Just look at those baby blues during this close-up shot from the Red Rock West party at Club USA in New York!
1994
Leo looked sweet as can be during the D.A.R.E. Benefit at Smashbox Studios in Culver City, CA, in 1994.
1995
And even though he probably should have gotten his hair trimmed before The Basketball Diaries' premiere in Westwood, CA, we still loved him.
1996
Romeo + Juliet rocketed Leo to superstardom, and he definitely dressed accordingly at the film's 1996 premiere in Los Angeles.
1996
Those are definitely the coloured lenses of a superstar.
1997
If Romeo + Juliet didn't put Leo on your radar, then he was impossible to ignore after Titanic [6], which premiered at Mann Chinese Theatre in Los Angeles in 1997.
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.
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.