He might be now known for dating a string of leggy blonde models and partying with his 'p**** posse' as well as his acting talents - but Leo looks like butter-wouldn't-melt in his high school yearbook picture.
Taken from his time at John Marshall High School in Los Feliz, California the young Leo looks heartbreakingly cute as he smiles for the camera.
Rocking the nineties favourite haircut - curtains - it's hard to believe this student would go on to become on of the biggest stars on the planet.
Even at this age though Leo was harbouring aspirations of becoming a Hollywood actor.
After starting out in commercials the now 41-year-old landed his first big role in 1990 sitcom Growing Pains and by 1993 was starring alongside Robert De Niro in This Boy's Life.
Even at this age it was pretty clear Leo was destined to be a heart-breaker, going on to make teenage girls swoon with roles in Romeo and Juliet and the iconic Titanic.
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