The Evolution of Leonardo DiCaprio: From ‘Growing Pains’ to ‘Once Upon a Time in Hollywood’ (Photos)

For nearly 30 years, Leonardo DiCaprio has managed to maintain an image as a handsome, Hollywood heartthrob and as one of the industry’s most bankable and pedigreed performers. While he’s consistently been at the top of the A-list, the roles DiCaprio has taken have changed dramatically. In “Once Upon a Time…in Hollywood,” DiCaprio lends his star power to help Quentin Tarantino shape a new Tinsel Town legend. Here’s how the actor has evolved over the years:

“Growing Pains” (1991)

After guest starring on “Roseanne” and “Parenthood,” DiCaprio landed a role on the long-running sitcom “Growing Pains.” He played Luke Brower, a homeless student in the class of young school teacher Mike (Kirk Cameron) that the Seaver family take in until he is reunited with his father.

“This Boy’s Life” (1993)

In his first major movie role, Leo landed the starring role alongside Robert De Niro and Ellen Barkin in the ’50s period drama “This Boy’s Life,” flashing a rebellious charisma and wildness that would come to define his future performances.

“What’s Eating Gilbert Grape” (1993)

DiCaprio earned his first Oscar nomination at the age of 19 in “What’s Eating Gilbert Grape.” Leo starred as the mentally challenged younger brother to Johnny Depp in Lasse Hallstrom’s tender family drama set in small town Middle America.

“The Basketball Diaries” (1995)

DiCaprio took a starring role in the autobiographical “The Basketball Diaries,” playing a teenage basketball star who falls into a drug addiction. The movie became the focal point for critics in the wake of the Columbine high school shooting based on a disturbing dream sequence in which DiCaprio’s character shoots six of his classmates with a shotgun while wearing a black trench coat.

“Romeo + Juliet” (1996)

In Baz Luhrmann’s modern rendition of the classic Shakespeare play “Romeo + Juliet,” DiCaprio transitioned to full-on Hollywood heartthrob opposite Claire Danes.

“Titanic” (1997)

DiCaprio becomes a household name came when he starred in “Titanic” as the charming, but poor, artist Jack Dawson. The movie went on to win 11 Oscars and become then the highest grossing movie of all time, but DiCaprio sadly did not win for Best Actor.

“The Man in the Iron Mask” (1998)

DiCaprio rocked longer tresses to embody King Louis XIV in “The Man in the Iron Mask.”

“The Beach” (2000)

Leo chopped his golden locks very short for his role in Danny Boyle’s “The Beach,” in which his character travels to a secret island in Thailand with a map and the hope to find a solitary beach paradise.

“Gangs of New York” (2002)

“Gangs of New York” would be the first of Leo’s many collaborations with director Martin Scorsese, leading a brutal gang drama set during Civil War era New York.

“Catch Me If You Can” (2002)

DiCaprio’s massive 2002 found him working with another legendary director and flashing his charm as Frank Abagnale Jr. in Steven Spielberg’s slick and fun biopic “Catch Me If You Can.” DiCaprio plays a real life con man who impersonated a pilot, doctor and legal prosecutor who swindled millions and became one of the FBI’s most wanted.

“The Aviator” (2004)

In his second Oscar-nominated performance, DiCaprio portrayed the early life of legendary tycoon, playboy and eccentric Howard Hughes in Martin Scorsese’s period epic “The Aviator.”

“The Departed” (2006)

Another Scorsese collaboration, DiCaprio and Matt Damon star alongside Jack Nicholson in Scorsese’s tense gangster story full of double crossing and thick Boston accents.

“Blood Diamond” (2006)

2006 would be another major year for DiCaprio, as he earned his third Oscar nomination for donning a thick South African accent in “Blood Diamond,” playing a diamond smuggler in Edward Zwick’s action thriller. But while it was a strong anti-hero performance, his third straight Oscar loss suggested he might’ve fared better with a nomination for Scorsese’s Best Picture winner “The Departed.”

“Revolutionary Road” (2008)

DiCaprio and his “Titanic” co-star Kate Winslet were reunited in “Revolutionary Road,” Sam Mendes’s suburban drama about a 1950s couple struggling with their mundane lifestyle. Though he won the Golden Globe for Best Actor in a Drama, the Academy snubbed him for a nomination.

“Shutter Island” (2010)

2010 would be another big year for DiCaprio in which his characters grew more tormented as they grappled with reality. In Scorsese’s “Shutter Island,” he plays a U.S. Marshall investigating a psychiatric facility, only to doubt his own sanity.

“Inception” (2010)

Also in 2010, DiCaprio had the biggest box office opening of his career when he starred in Christopher Nolan’s mind-bending thriller “Inception.” DiCaprio was a natural as a master thief who used dreams as a way to stage the ultimate heist, all as he battles his own mental demons.

“J. Edgar” (2011)

DiCaprio teamed with another legendary director in Clint Eastwood for a biopic on the life of FBI director J. Edgar Hoover. DiCaprio donned another accent and heavy makeup to portray Hoover across 50 years of his life.

“Django Unchained” (2012)

DiCaprio had never played the villain before Quentin Tarantino cast him as a despicable, racist slave owner in his Western “Django Unchained.” DiCaprio went to great lengths to embody the brutal, fiery personality of his character. DiCaprio told THR he stayed in character and kept filming after getting a bloody cut on his hand, a take that ended up making the final cut of the film.

“The Great Gatsby” (2013)

DiCaprio shifted back into handsome charmer mode with a dark side for Baz Luhrmann’s colorful take on F. Scott’s Fitzgerald’s American classic “The Great Gatsby,” giving the world a gif for the ages in the process.

“The Wolf of Wall Street” (2013)

In his fifth movie with Martin Scorsese, “The Wolf of Wall Street,” DiCaprio portrayed the outlandish rise and fall of infamous stockbroker Jordan Belfort. The performance is among the most energetic and over the top of his career, and he earned two Oscar nominations for his work, one for Best Actor and another for producing.

“Virunga” (2014)

DiCaprio has had a long career as a producer, but he made a name for himself as a leading advocate for climate change and wildlife preservation beginning with the Oscar-nominated documentary he executive produced, “Virunga.” The film was acquired by Netflix and follows a group of individuals who fight dangerous conditions to protect some of the world’s last remaining mountain gorillas. DiCaprio would follow up that effort with other critically acclaimed docs such as “Sea of Shadows,” “Before the Flood” and “Ice on Fire.”

“The Revenant” (2015)

DiCaprio gave all of himself in a punishing, excruciating shoot for Alejandro Inarritu’s “The Revenant,” trudging through nature and even shielding himself in a horse’s carcass for warmth to portray the  19th-century frontiersman named Hugh Glass. The physical performance paid off, as DiCaprio finally won his Oscar after losing four straight times.

Academy Awards (2016)

Upon winning the Oscar for Best Actor, DiCaprio also used his acceptance speech to advocate for action on climate change. “It is the most urgent threat facing our entire species, and we need to work collectively together and stop procrastinating,” he said.

“Once Upon a Time…in Hollywood” (2019)

DiCaprio returned to the screen for the first time in four years since winning his Oscar to again team up with Quentin Tarantino. In “Once Upon a Time…in Hollywood,” DiCaprio stars alongside Brad Pitt and his “Wolf of Wall Street” co-star Margot Robbie as a washed up movie star trying to make it back on top during a massive period of change in 1969 Hollywood around the time of the Manson Family murders.