With the momentum garnered by wins at the Golden Globes and the SAG Awards, and ample talk of the grueling preparations for his role in The Revenant, Leonardo DiCaprio is preparing for what may be—if it materializes as expected—his biggest moment ever: recipient of the Academy Award for Best Actor. But long before he was a twinkle in Alejandro Iñárritu‘s eye, he was a babe in his mother’s arms, a sandy-haired child actor mugging for promotional shots and a young dreamboat papering the walls of tween-age bedrooms.

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Write to Eliza Berman at eliza.berman@time.com.

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