A lovely look at Leonardo DiCaprio from the 90s until now

Leonardo DiCaprio is revered as one of the most beloved and talented actors of our time. His name is synonymous with some of the best films and roles ever. There truly is no comparison. 

The last time Leonardo DiCaprio graced our presence on screen was in the Quentin Terentino film Once Upon a Time is Hollywood with actors Brad Pitt and Margot Robbie. After a year and a half hiatus, Leonardo DiCaprio is finally back, giving us something to look forward to in 2021

Leonardo DiCaprio recently departed Boston and wrapped up filming for Don’t Look Up, a political satire directed by Adam McKay about the end of the world. The star-studded lineup includes Jennifer Lawrence, Timothee Chalamet, and Meryl Streep.

As Leonardo DiCaprio wraps up filming Don’t Look Up, we can’t help but look back on the journey that brought him to where he is today. 

Let’s get some Leonardo DiCaprio basics out of the way first

Leonardo Wilhelm DiCaprio is an American actor, producer, and philanthropist. The celebrity is known for his edgy and diverse roles, starring in blockbuster Hollywood movies including Titanic and The Great Gatsby

Between acting, producing, and philanthropic work, Leonardo DiCaprio has built quite a life for himself. Leonardo DiCaprio’s net worth is reported to be $260 million. He owns seven homes in California, two luxury apartments in New York, and a private island that he hopes to turn into an eco-friendly resort. 

Despite all of his success and fortune, Leonardo DiCaprio has not always lived a privileged life. Leonardo DiCaprio’s age is 47 and he was born in Los Angeles on November 11th, 1974. He’s the only child of Irmelin Indenbirken and George Dicaprio

According to Vanity Fair, his parents named him after Leonardo Da Vinci when his pregnant mother felt him kick for the first time while admiring a Leonardo Da Vinci painting. 

Early in his childhood, Leonardo DiCaprio’s parents separated and he began living with his mother, Irmelin Indenbirken, full-time. While still remaining close with his father, the mother-son duo developed a strong bond early on, and he credits most of his success to her. In a 1994 interview with Interview Magazine, the actor lovingly spoke about his relationship with his mother and father:

“My parents . . . were so good at keeping my environment strong and keeping everything around me not focused on the fact that we were poor. They got me cultured. They took me to museums. They showed art to me. They read to me. And my mother drove two hours a day to take me to University Elementary School.”

Leonardo Dicaprio made the decision to drop out of high school to pursue acting. Leonardo DiCaprio’s mother, Irmelin Indenbirken, supported him wholeheartedly. 

Throughout his early career, Leonardo Dicaprio continued to live with his mother until he hit mega-stardom with his role as Jack in the Titanic cast alongside Kate Winslet (Titanic fans, you’ll love seeing the cast of Titanic then vs. now). 

Even now, Leonardo DiCaprio’s mother is still the leading lady in his life, accompanying him to award shows like The Golden Globes and the Oscars. She is always right by his side to cheer him on. 

Now, a look at Leonardo DiCaprio’s on-screen evolution

While his leading role as part of the Titanic cast granted Leonardo Dicaprio instant success, a long string of revered TV and movie roles led him to his A-List celebrity status, both before and after the premiere of Titanic

In the early 1990’s, after constant auditions, Leonardo Dicaprio finally landed a recurring role on Growing Pains. From 1991 to 1992, Dicaprio played Luke Bowers, a homeless boy that the Seaver family takes in. Leonardo DiCaprio’s co-star Joanna Kerns described him as “intelligent and disarming for his age” while also being “mischievous on set.”

In 1993, Leonardo Dicaprio starred alongside Robert De Niro in The Boys Life, a hidden gem based on the memoir by Tobias Wolf. This role was pivotal in his career, because even at a young age, Leonardo DiCaprio was able to show the complexities of the character while keeping up with the legendary Robert De Niro

In 1993, Leonardo DiCaprio starred alongside Johnny Depp in What’s Eating Gilbert Grape as Arnie Grape, often considered his breakout role, resulting in the very first Oscar nomination for Leonardo DiCaprio at just 19 years old. 

Eventually, Titanic came along, and Leonardo DiCaprio became the quintessential 90’s heartthrob to teen girls across the world. All Titanic fans remember the scene when 90s Leonardo DiCaprio melts us as Jack, who is completely awestruck by Rose’s beauty as she walks down the stairway––the chemistry is undeniable!  

In 2014, Leonardo DiCaprio publicly acknowledged how pivotal his role in the Titanic cast was for his entire career, saying in an interview on This Morning that the film “was such a huge part of my life…I’m incredibly proud of it. And not only that, the movie has really made me be in control of my career.”

Funnily enough, both Kate Winslet and Leonardo DiCaprio reportedly have looked back on their performances and cringe––they’re not the only actors who feel that way about roles that made them famous.

Related: Here’s What Your Favorite Disney Characters Would Look Like If They Starred in Titanic

Kate Winslet and Leonardo DiCaprio’s chemistry stands the test of time both on and off screen––they have remained best friends for over 23 years. 

When Kate Winslet won the Golden Globe for Revolutionary Road in 2009, she honored her long time friend in her acceptance speech

 “Leo, I’m so happy I can stand here and tell you how much I love you and how much I’ve loved you for 13 years. I love you with all my heart, I really do.”

With this undying support, Leonardo DiCaprio went to star in Martin Scorsese’s The Wolf of Wall Street and Quentin Tarantino classics including Django Unchained and Once Upon a Time in Hollywood. 

Kate Winslet and Leonardo DiCaprio aren’t the only dynamic duo. Over the past two decades, Leonardo DiCaprio and Martin Scorsese have developed a strong and supportive working relationship with one another. The pair have a total of five collaborations to date, including The Aviator, The Departed, and The Wolf of Wall Street, and currently have two more projects in the works. We break down every single one of their collaborations in this article).

Robert De Niro initially recommended that Martin Scorsese work with the young actor, and Martin Scorsese listened. He speaks of Leonardo DiCaprio fondly, and the mutual respect and love they have for each other is evident. In the past, Martin Scorsese has said: 

“We’re a different generation, but he goes in the same places that I want to go. He’s not afraid to go there. He’s not afraid to deal with that part of himself and that’s interesting. We have a different context, we grew up differently, but I think we speak the same language emotionally and psychologically. It’s very lucky.”

Leonardo DiCaprio credits much of his success to working with Martin Scorsese who pushes the boundaries when it comes to his roles.

In 2016, Leonardo DiCaprio pushed every boundary and finally won his long-overdue Oscar for Best Actor in The Revenant.

Leonardo DiCaprio’s impact on environmental issues make him both an actor and celebrity activist

In his 2016 Oscars acceptance speech for The Revenant, Leonardo DiCaprio used his platform to address climate changes issues:

“Climate change is real, it is happening right now, It is the most urgent threat facing our entire species, and we need to work collectively together and stop procrastinating. We need to support leaders around the world who do not speak for the big polluters, but who speak for all of humanity, for the indigenous people of the world, for the billions and billions of underprivileged people out there who would be most affected by this. For our children’s children, and for those people out there whose voices have been drowned out by the politics of greed.”

Well before his Oscar win, Leonardo DiCaprio devoted time, resources, and money to save the planet when he wasn’t busy acting.

The actor and celebrity activist has been focused on climate change and environmental issues since early on in his career and has established himself as one of the top climate change leaders of our generation.

In 1998 at just 24 years old, this celebrity activist founded the Leonardo Dicaprio Foundation. The organization’s mission is to “support projects around the world that build climate resiliency, protect vulnerable wildlife, and restore balance to threatened ecosystems and  communities.”

Years later, Leonardo DiCaprio continues his fight for climate change. Most recently, he wrote an open letter to Joe Biden to ensure that the president puts environmental issues at the forefront of his presidency. 

Leonardo DiCaprio knows addressing climate change is an enormous task, but he is willing to dedicate his life to make it happen. 

A look at a few Leonardo DiCaprio movies we all know and love

Leonardo DiCaprio, without a doubt, has it all. The brains, the looks, the talent, and the versatility to play any role he chooses. He has graced our presence on and off-screen for over three decades, so now seems to be a good time to pick some of our favorite Leonardo DiCaprio movie masterpieces. 

Leonardo DiCaprio Movies: Romeo + Juliet (1996)

In Baz Lurhman’s adaptation of the Shakespere classic, Leonardo DiCaprio and Claire Danes play star-crossed lovers in the post-modern Verona Beach. You can rent this classic 90’s romantic movie on Amazon Prime and check out 10 facts you didn’t know about Romeo + Juliet.

Leonardo DiCaprio Movies: Gangs of New York (2002) 

The 9-time Oscar-nominated film directed by Martin Scorsese is revered as a “punishing piece of work” by Film Comment. Leonardo DiCaprio plays an immigrant seeking revenge against his father’s killer, played by Daniel Day-Lewis, creating an epic tale of vengeance and survival. Did you know that Leonardo DiCaprio begged Martin Scorsese to work with him on this movie? This Leonardo DiCaprio movie is available to watch through Cinemax on Amazon Prime. 

Leonardo DiCaprio Movies: Django Unchained (2012)

The rivalry continues with this 2012, Quentin Tarantino film where Leonardo DiCaprio plays Calvin Candie, an inhumane plantation owner, alongside Hollywood actors Jaime Foxx and Christoph Waltz. “He was one of the most deplorable, indulgent, horrendous characters I’ve ever read in my life,” Leonardo DiCaprio recalls in an interview. In honor of Django Unchained, we run through the greatest spaghetti westerns ever made. Watch Leonardo DiCaprio in Django Unchained now on Netflix.

Leonardo DiCaprio Movies: The Great Gatsby (2013)

Baz Lurhmann crafted a glamorous, over-the-top spectacle when recreating this classic novel. Leonardo DiCaprio was the first cast for this film as Jay Gatsby. Tobey Maguire plays Gatsby’s friend and is the narrator of the film, Nick Carraway. In our original review, we said “like the sporadic beauty of jazz, [Leonardo] DiCaprio mixes Gatsby’s moods into one enchanting character.” See this spectacular reboot on Amazon Prime

Leonardo DiCaprio Movies: Once Upon a Time in Hollywood (2019)

Serving as a laid-back period piece, this movie is a respectable addition to the Quentin Tarantino movie library. The friendship of Rick Dalton (Leonardo Dicaprio) and Cliff Booth (played by Brad Pitt––apparently everyone wanted his role?!) serves as the core of the film. Leonardo DiCaprio’s character is described as “one of the filmmaker’s finest creations, a character upon whom Tarantino has projected some of his own self-seriousness.”

Leonardo DiCaprio, meme king 

Leonardo DiCaprio is not only a multi-faceted actor, producer and celebrity activist, but he is also the king of memes. Most of the Leonardo DiCaprio memes include him with a drink in one hand and a signature Leonardo DiCaprio facial expression.

One scene that inspired the internet to start meming Leonardo DiCaprio is the climax scene in Django Unchained where he is seen laughing and dining with a table full of people.

In honor of Hollywood’s king of memes, we dug up some of our favorite Leonardo DiCaprio memes:

 

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Leonardo DiCaprio at "The Beach" Premiere
 Leonardo DiCaprio at "The Beach" Premiere
Ken Kwok
Star Leonardo DiCaprio brought his own camera crew to film the premiere for his Web site.
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77th Annual Academy Awards RC: Leonardo DiCaprio
77th Annual Academy Awards RC: Leonardo DiCaprio
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77th Annual Academy Awards RC: Leonardo DiCaprio
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77th Annual Academy Awards RC: Leonardo DiCaprio
77th Annual Academy Awards RC: Leonardo DiCaprio
Adriana M. Barraza
77th Annual Academy Awards RC: Leonardo DiCaprio
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Leonardo DiCaprio
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Kate Winslet and Leonardo DiCaprio at the World Premiere of 'Revolutionary Road'.
Kate Winslet and Leonardo DiCaprio
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Kate Winslet and Leonardo DiCaprio at the World Premiere of 'Revolutionary Road'. Mann Village Theater, Westwood, CA. 12-15-08
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Leonardo DiCaprio at the World Premiere of 'Revolutionary Road'
Leonardo DiCaprio
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Leonardo DiCaprio at the World Premiere of 'Revolutionary Road'. Mann Village Theater, Westwood, CA. 12-15-08
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Robert De Niro, Martin Scorsese and Leonardo DiCaprio at the 67th Annual Golden Globe Awards Press Room
Robert De Niro, Martin Scorsese and Leonardo DiCaprio
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Robert De Niro, Martin Scorsese and Leonardo DiCaprio at the 67th Annual Golden Globe Awards Press Room, Beverly Hilton Hotel, Beverly Hills, CA. 01-17-10
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Leonardo DiCaprio at the AFI Fest 2011 Opening Night Gala Premiere of "J. Edgar,"
Leonardo DiCaprio
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Leonardo DiCaprio at the AFI Fest 2011 Opening Night Gala Premiere of "J. Edgar," Chinese Theater, Hollywood, CA 11-03-11
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What is Leonardo DiCaprio doing now?

These days, Leonardo DiCaprio is busy filming Killers of the Flower Moon, a film directed by none other than Martin Scorsese. It’s based on a true story about the Osage tribe and their murders. Leonardo DiCaprio and Martin Scorsese met with culturals leaders of the tribe to ensure the film was as historically correct as possible

We can’t wait to make a movie date to see this movie––would you believe it’s the first time Leonardo DiCaprio, Martin Scorsese, and Robert De Niro are all teaming up together on one feature-length film?

In his free time, Leonardo DiCaprio spends time with his long-time girlfriend of over three years, Camila Morrone. Sorry ladies, he’s officially off the market––for now––and the couple doesn’t care about their age gap, either.

Leonardo DiCaprio’s girlfriend Camila Morrone is a former model and actress on the rise most known for her 2020 role in Mickey and the Bear, now available to watch on Hulu Premium. 

With a beautiful girlfriend and new projects on the horizon, Leonardo DiCaprio has no problem keeping busy. We all just need to be patient while we eagerly await the next Leonardo DiCaprio movie masterpiece. 

In the meantime, his most recent film (Once Upon in Hollywood) is streaming on STARZ on Amazon Prime, so we can appreciate his gripping and amusing performance as Rick Dalton. 

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