Now 50, Leonardo DiCaprio is nothing short of a Hollywood powerhouse—the industry’s quintessential leading man, with an Oscar, BAFTA, SAG Award, two Critics’ Choice Awards, and three Golden Globes to his name, accumulated over the course of an unparalleled four-decade-long career with towering performances in everything from Romeo + Juliet and Titanic to Catch Me If You Can, The Aviator, The Departed, Revolutionary Road, The Wolf of Wall Street, The Revenant, and Killers of the Flower Moon.
But before he became entirely ubiquitous, the Los Angeles native was a child star in the late 1980s and early ’90s, a frequent presence in commercials and sitcoms including NBC’s Parenthood and ABC’s Growing Pains.
It was his part in What’s Eating Gilbert Grape opposite Johnny Depp that then set him on a path to the A-list at the age of 19, securing him a best-supporting-actor Oscar nomination and a string of more prominent roles, including the swoon-worthy romantic hero in Baz Luhrmann’s vivid reimagining of the bard’s best-known tragedy, and the free-spirited artist Jack Dawson in a certain Academy Awards-sweeping, box-office-record-breaking, James Cameron-directed cultural phenomenon. After that, there was no looking back.
In honor of his birthday, we present 27 jaw-dropping throwback photos of the actor, from his childhood to the remarkable first decade of his career.
Photo: Getty Images1/271975
At just a few months old, Leonardo DiCaprio is held up by his mother, Irmelin—now a regular red carpet plus-one—in their Los Angeles home.
Photo: Getty Images2/271975
DiCaprio as a toddler, already a natural in front of the camera.
Photo: Getty Images3/271978
An adorable, three-year-old, bowl cut-sporting, boilersuit-wearing Leo with his older stepbrother, Adam Ferrar, posing on the porch of their LA home. A year later, the future Hollywood stalwart would appear onscreen for the first time, in the children’s TV show Romper Room.
Photo: Getty Images4/271989
A 14-year-old Leo, in a Nike bomber jacket and with floppy hair, on the phone in 1989, the year he made his formal acting debut in the family drama series The New Lassie after appearing in a string of commercials.
Photo: Getty Images5/271989
Already seeming to channel his character’s style in Baz Luhrmann’s 1996 hit Romeo + Juliet in a graphic shirt.
Photo: Getty Images6/271990
After parts in Fox’s The Outsiders and the NBC soap opera Santa Barbara, DiCaprio’s life changed when he was cast in the Ron Howard-produced sitcom Parenthood at the age of 15. He’s pictured here on set alongside co-star Max Elliott Slade.
Photo: Getty Images7/271990
A composed young DiCaprio poses for a studio portrait in a camo jacket, plaid shirt, and jeans to promote Parenthood.
Photo: Getty Images8/271990
In a white T-shirt, black trousers, and slicked-back hair for a LA press conference while on the promo trail for Parenthood.
Photo: Getty Images9/271992
A 17-year-old DiCaprio in basketball gear for an MTV event in LA. Then a regular on ABC’s Growing Pains, he was on the cusp of his Hollywood breakout.
Photo: Getty Images10/271993
In a white shirt, black suit, and long necklace for the LA premiere of This Boy’s Life, in which an 18-year-old DiCaprio starred alongside Robert De Niro and a 17-year-old Tobey Maguire.
Photo: Getty Images11/271993
A rain-soaked DiCaprio in a leather jacket, shirt, and beaded necklace at the LA premiere of Benny & Joon.
Photo: Getty Images12/271993
In a collared sweatshirt and T-shirt for the LA premiere of Christian Slater and Patricia Arquette’s True Romance.
Photo: Getty Images13/271993
A 19-year-old DiCaprio hanging out with a 22-year-old Mark Wahlberg.
Photo: Getty Images14/271993
Sporting brown suede, blue jeans, a black shirt, and a white T-shirt for the LA premiere of Brian De Palma’s Carlito’s Way.
Photo: Getty Images15/271993
In a black suede jacket, T-shirt, and beaded necklace, the actor attends the LA premiere of What’s Eating Gilbert Grape, the coming-of-age drama for which he’d go on to earn his first Oscar nomination for best supporting actor.
Photo: Getty Images16/271993
In a dark blue suit for the Los Angeles Film Critics’ Awards, where DiCaprio took home the New Generation Award for his parts in This Boy’s Life and What’s Eating Gilbert Grape.
Photo: Getty Images17/271994
Dapper at his first Golden Globes at the age of 19, where he was nominated for best supporting actor for What’s Eating Gilbert Grape.
Photo: Getty Images18/271994
The classic DiCaprio pairing of a louche suit and beaded necklace for the LA premiere of Winona Ryder and Ethan Hawke’s Reality Bites.
Photo: Getty Images19/271994
Dreamy in a black velvet shirt at a benefit in LA.
Photo: Getty Images20/271994
With Gwyneth Paltrow, then a 21-year-old industry newcomer, at a National Board of Review event in New York.
Photo: Getty Images21/271994
In a bow tie and tux for his first Oscars, the year he was nominated for his part in What’s Eating Gilbert Grape.
Photo: Getty Images22/271994
In a loose knit and beaded necklace for a portrait session in LA.
Photo: Getty Images23/271994
Pictured in yet another textured knit and beaded necklace combo in 1994.
Photo: Getty Images24/271995
Aged 20, and making the indelible pairing of a pinstripe suit, an exaggerated collar, and a gold necklace look oddly appealing at the New York premiere of The Basketball Diaries, in which he plays a troubled high schooler.
Photo: Getty Images25/271996
At the LA premiere of Romeo + Juliet, aged 21, with a 17-year-old Claire Danes.
Photo: Getty Images26/271997
With spiky hair at the LA premiere of Titanic, aged 22.
Photo: Getty Images27/271998
A 23-year-old DiCaprio at the Golden Globes with a 22-year-old Kate Winslet, the year they were nominated for best actor and actress in a motion picture – drama, respectively, for Titanic. The blockbuster left the ceremony with four statuettes, including the prize for best motion picture – drama.
