60 Photos That Display the Eternal Cool of Leonardo DiCaprio

leonardo dicaprio
Leonardo DiCaprio's Life in PhotosCatherine McGann - Getty Images

Here's a fun fact: Leonardo DiCaprio has been a working actor for over three decades. But reaching his current A-list status didn't happen overnight. If you need a reminder of his roles over the years—and feel like tussling with us in the comments section—you can head over to our ranking of every single one of his movies.

Now, the actor has a new film in theaters, with Killers the Flower Moon standing as another triumph for both DiCaprio and his longtime collaborator, Martin Scorsese. That means it's time to look back at the legendary actor's career and personal life over the years—from his days on TV to his breakout role in Titanic to finally winning the Academy Award for Lead Actor in 2016. (For what, you ask? His brawl with a big ol' bear in The Revenant, of course.) Let's dive in.

1975: Baby Leo

Leonardo DiCaprio was born on November 11, 1974 in Los Angeles. He was named after the famous painter Leonardo da Vinci, because his mom first felt him kick while looking at one of his paintings.

Leonardo DiCaprio and his mother Imelin
Peter Fleming Photos - Getty Images

1975: A Broken Home

DiCaprio's mom and dad divorced when he was only one. He was was primarily raised by his mother, Irmelin Indenbirken.

Leo DiCaprio And His Brother Adam
Peter Fleming Photos - Getty Images

1978: The Little Brother

The actor's future stepmother, Peggy Anne Farrar, and her son, Adam, moved in with DiCaprio's father when he was just a baby and the pair married in 1995. DiCaprio's stepbrother pursued acting first and was cast in a series of commercials as a child.

Leo DiCaprio And His Brother Adam
Peter Fleming Photos - Getty Images

1989: A Young Actor

DiCaprio followed in Adam's footsteps and started acting in commercials for brands like Kraft Singles and Bubble Yum in the late '80s before transitioning to television.

Leonardo DiCaprio Talks On Telephone, c. 1989.
Darlene Hammond - Getty Images

1990: His First Show

The young actor snagged his first major role on TV as Garry Buckman on NBC's Parenthood, starring alongside David Arquette (far right). The show only lasted one season.

NBC - Getty Images

1991: A New TV Family

His time on Parenthood caught the attention of ABC network execs, which led to DiCaprio being cast as the newest member on the hit sitcom, Growing Pains.

ABC Photo Archives - Getty Images

1992: Celebrity Status

By 1992, DiCaprio was television's bright new star. Here, he's pictured competing in MTV's Rock 'n Jock basketball tournament, alongside Joey Lawrence from Blossom and Ian Ziering from 90210.

1992 MTV Rock 'n' Jock Basketball
Jeff Kravitz - Getty Images

1993: Back-to-Back Films

In 1993, the actor made his first appearance in a movie in This Boy's Life, which costarred Robert De Niro and Ellen Barkin.

On the set of This Boy's Life
Sunset Boulevard - Getty Images

1993: A Major Movie

In 1993, he filmed What's Eating Gilbert Grape alongside Johnny Depp. He earned his first Oscar nomination for Best Supporting Actor for his work in the role. Here he's with his mom at the premiere.

Whats Eating Gilbert Grape Premiere
Barry King - Getty Images

1993: A Rising Star

With two hit movies and an Oscar nomination in one year, the actor was poised to become the next big thing in Hollywood.

Ron Davis - Getty Images

1994: His First Girlfriend

DiCaprio's first public relationship was with Victoria's Secret model Bridget Hall. The two were first linked in 1994.

Bridget Hall;Leonardo Dicaprio
Photo by Dave Allocca/DMI/The LIFE Picture Collection - Getty Images

1994: An Entourage

The actor has been part of a group of famous friends for years. Even though Mark Wahlberg's HBO show Entourage is loosely based on his own time as a young star, it's been said that DiCaprio also served as an inspiration for the main character.

Mark Wahlberg, Leonardo DiCaprio
Photo by The LIFE Picture Collection - Getty Images

1994: The Best Date

DiCaprio's mom has long served as his date to premieres and award shows, and the 1994 Golden Globes were no exception. The actor earned his first nomination for his role in What's Eating Gilbert Grape and Indenbirken showed her support on the red carpet.

51st Annual Golden Globe Awards
Jim Smeal - Getty Images

1994: The Academy Awards

Even though 1994 was DiCaprio's first time at the Academy Awards, he's since returned many times throughout his career.

66th Annual Academy Awards
Barry King - Getty Images

1995: Back on Set

The actor followed his initial success in movies with the lead role in The Quick and the Dead in 1995.

On the set of The Quick and the Dead
Sunset Boulevard - Getty Images

1995: Filming 'Total Eclipse'

Another fringe film he starred in was the 1995 movie Total Eclipse in which he played Arthur Rimbaud.

On the set of Total Eclipse
Etienne George - Getty Images

1995: Another Big Premiere

DiCaprio arrives at the premiere of The Basketball Diaries, his third film, which released in 1995.

<span class="photo-credit">Jim Smeal - Getty Images</span>
Jim Smeal - Getty Images

1995: A Relationship Rumor

Over the years, DiCaprio has been linked to some of fashion's most famous models. including Naomi Campbell in the mid-'90s. The two never confirmed a romantic status, but they remain friends today.

Grand Opening of Seventh On Sale
Ron Galella - Getty Images

1995: Friends First

The actor has been friends with David Blaine and Lukas Haas for decades. Here, the group is seen together early on in their friendship.

David Blaine, Leonardo DiCaprio and Lukas Haas
Patrick McMullan - Getty Images

1996: Starring as Romeo

DiCaprio was cast to play Romeo in the modern day adaption of Romeo and Juliet in 1996. His costar, Claire Danes, was another buzzy up-and-coming actor in Hollywood at the time.

<span class="photo-credit">Barry King - Getty Images</span>
Barry King - Getty Images

1996: Grandma's Red Carpet Debut

The actor's penchant for escorting family members to red carpet events doesn't stop at his mom. In 1996, it was his grandmother who got her turn to walk the red carpet at the Cannes Film Festival.

Cannes Film Festival 1996
Pool ARNAL/GARCIA/PICOT - Getty Images

1996: Young Love

Model Kristen Zang was the actor's first serious girlfriend. The pair began dating in 1996 and were together for two years.

<span class="photo-credit">SGranitz - Getty Images</span>
SGranitz - Getty Images

1997: Working With Woody Allen

DiCaprio was in director Woody Allen's film, Celebrity, in the late '90s.

Lawrence Schwartzwald - Getty Images

1997: A Movie Called 'Titanic'

Even though DiCaprio was famous before the 1997 hit, the actor reached another level of fame after the release of Titanic. His role as Jack Dawson earned him critical acclaim, a trip to the Academy Awards, and the adoration of teenage girls everywhere.

<span class="photo-credit">Jeff Kravitz - Getty Images</span>
Jeff Kravitz - Getty Images

1998: More Than Costars

Rose and Jack—we mean, Leo and Kate Winslet, stole audience's hearts with their tragic love story. Though the actors swear nothing romantic transpired, the two built a lifelong friendship. "I'm not going to tell you what we actually talk about, but yeah, we're very, very close and sometimes we do quote the odd Titanic line back and forth to each other, because only we can, and we find it really funny," Winslet told Glamour UK about her relationship with the actor.

55th Annual Golden Globe Awards
Jim Smeal - Getty Images

1998: Meeting Royalty

DiCaprio brought his grandmother along for the premiere of The Man in the Iron Mask so that she could meet Prince Charles. (Don't worry: His mom got her chance to meet the royals at the London premiere of Titanic a year earlier.)

Leonardo DiCaprio/ PoW
Peter Jordan - PA Images - Getty Images

1999: Stars, They're Just Like Us

Sometimes all it takes is a couple of Star Wars action figures in the checkout line at Target at 1:30 a.m. to remind you that A-list celebrities are people too.

05/03/99. Santa Monica, CA. Leonardo DiCaprio shops for Star Wars Toys at the ''Toys R'' Us'' store
Dan Callister - Getty Images

2000: Filming 'The Beach'

DiCaprio got to spend some time in Thailand while on location filming The Beach in 2000.

Leonardo DiCaprio In 'The Beach'
20th Century Fox - Getty Images

2000: A New Romance

In 2000, DiCaprio was linked to model Gisele Bündchen. Given his loyal Lakers fan status, the couple made many courtside appearances.

Celebrities Attend Lakers v Jazz Game
Vince Bucci - Getty Images

2001: Premiere of 'Gangs of New York'

Renowned director Martin Scorsese reportedly heard of DiCaprio from Robert De Niro and 2001, Scorsese cast the actor in Gangs of New York. The two have since gone on to collaborate on many films.

US director Martin Scorsese (C), US actor Leonardo

2002: Eco Activist

DiCaprio has been a passionate advocate for the environment for decades. In 2002, he singed a letter to then-President George W. Bush to raise awareness for the Earth Summit.

Rock The Earth Summit Party in Hollywood
Vince Bucci - Getty Images

2002: Say Hi to Frank and...Frank

The actor arrives at the premiere of his 2002 film Catch Me If You Can with the real-life '60s con-man-turned-government-informant, Frank Abagnale Jr.

DreamWorks Premiere of Catch Me If You Can - Jeff Kravitz
Jeff Kravitz - Getty Images

2004: Traveling the World

DiCaprio and Bündchen participated in a global exchange program where they traveled to the Amazon to raise awareness about the effects climate change was ravaging on the the Xingu people's fragile eco-system.

Gisele Bundchen and Leonardo DiCaprio with Xingu Indians in the Amazon Rainforest
Ronnie Taylor - Getty Images

2005: A Golden Globe Win

The actor's role in Aviator, in which he portrayed Hollywood golden age director John Hughes, earned him his first Golden Globe for Best Actor.

62nd Annual Golden Globe Awards - Pressroom
Kevin Winter - Getty Images

2005: Another Break Up

After a rare public appearance on the Academy Awards red carpet, DiCaprio and Bündchen called it quits in 2005. The pair had been dating since 2000 and it was the actor's longest relationship to date.

The 77th Annual Academy Awards - Red Carpet
KMazur - Getty Images

2006: A Star Cast

DiCaprio teamed up with some of Hollywood's heaviest hitters, including his The Basketball Diaries costar Mark Wahlberg, for the 2006 film The Departed. This role earned the actor another Golden Globe nomination.

Warner Bros. Pictures Premiere Of
Evan Agostini - Getty Images

2006: Another Relationship

DiCaprio seemed to bounce back from his relationship with Bündchen quickly with another Victoria's Secret model. The actor began dating Bar Refaeli after meeting her in Las Vegas in 2005.

Leonardo Di Caprio Sighting In Paris
Marc Piasecki - Getty Images

2006: And...Another Hit

That same year, the actor also earned another Oscar nomination for his role in the critically acclaimed film, Blood Diamond.

Premiere Of Warner Bros.
Kevin Winter - Getty Images

2007: Working Behind the Camera

The actor then tried his hand at writing and producing in 2007 with the documentary The 11th Hour. The film focuses on the urgent effects of climate change on the environment.

The 11th Hour Los Angeles Premiere - Arrivals
Jon Kopaloff - Getty Images

2008: Costars Reunite

Winslet and DiCaprio reunited onscreen in 2008. The famous friends starred as a mid-century married couple in Revolutionary Road.

Premiere Of Paramount Vantage's
Kevin Winter - Getty Images

2011: A Brilliant Biopic

In a year full of biopics, DiCaprio's role as J. Edgar Hoover in the 2011 film J. Edgar lead the charge in Hollywood in 2011.

AFI FEST 2011 Presented By Audi -
Frederick M. Brown - Getty Images

2011: Another Split

After being off-and-on for years, Refaeli and DiCaprio broke up in 2011.

Celebrities At The Lakers Game
Noel Vasquez - Getty Images

2012: A New Scorsese Project

DiCaprio paired up with director Martin Scorsese again in 2012 for The Wolf of Wall Street, a movie that dominated the box office and earned the actor his fourth Academy Award nomination.

On Location For
Bobby Bank - Getty Images

2013: A Classic Film

In 2013, the actor put his mark a classic story: The Great Gatsby.

<span class="photo-credit">Stephen Lovekin - Getty Images</span>
Stephen Lovekin - Getty Images

2013: Major Strides in Conservation

In 2013, DiCaprio worked with the auction house, Christie's, for a fundraising project for the The Leonardo DiCaprio Foundation.


2014: A New Look

After taking a break from the spotlight, DiCaprio attended his foundation's annual gala with a beard and man bun. The new hairstyle caused a frenzy online, but it turned out it was for an upcoming role.

Leonardo Dicaprio Foundation Inaugurational Gala In Saint -Tropez - Dinner & Auction
Dominique Charriau - Getty Images

2016: The Long-Awaited Oscar Win

DiCaprio won an Oscar for Best Actor at the 88th Annual Academy Awards for his role in The Revenant. This was his fifth nomination and first win.

88th Annual Academy Awards - Backstage And Audience
Christopher Polk - Getty Images

2016: Combining His Passions

In keeping with his environmental interests, DiCaprio produced the film Before the Flood in 2016, along with a number of other environmentally-focused documentaries.

Screening Of National Geographic Channel's
Gabriel Olsen - Getty Images

2018: A New Girlfriend

In 2018, DiCaprio began dating model Camila Morrone. They were together for several years before eventually calling the relationship off in 2022.

Paris Saint-Germain v Liverpool - UEFA Champions League - Group C - Parc Des Princes
Mike Egerton - PA Images - Getty Images

2019: Playing an Actor, Tarantino Style

Once Upon a Time... in Hollywood saw DiCaprio working with director Quentin Tarantino again. (They previously collaborated on Django Unchained.) He also teamed up with former The Wolf of Wall Street costar, Margot Robbie, and longtime friend, Brad Pitt.


2020: CORE Gala Dinner

DiCaprio let loose at a gala dinner to benefit the nonprofit CORE, alongside Beck and Sean Penn, who was the host for the evening.

core gala a gala dinner to benefit core and 10 years of life saving work across haiti around the world
Kevin Mazur - Getty Images

2020: Presenting De Niro a SAG Award

At the 26th Screen Actors Guild Awards, DiCaprio presented fellow legend Robert De Niro a well-deserved Lifetime Achievement Award, almost 30 years after they first worked together on-screen in A Boy’s Life.

26th annual screen actorsnbspguild awards inside
Kevork Djansezian - Getty Images

2020: Unsurprising Oscar Nominee

DiCaprio's performance as Rick Dalton in Once Upon A Time... In Hollywood earned him a sixth Oscar nomination. While Leo looked incredibly cool at the ceremony, Joaquin Phoenix ended up taking home the trophy that year for his performance as Arthur Fleck in Joker.

92nd oscars nominees luncheon arrivals
Steve Granitz - Getty Images

2020: Shooting ‘Don’t Look Up’

DiCaprio had the lead role in this apocalyptic dark comedy, which followed scientists who can’t get the world to care about a comet that will end human civilization when it impacts Earth. Production was delayed due to the Covid-19 pandemic, but shooting began in November 2020 with safety precautions in place.

dicaprio and lawrence shoot dont look up at south station
Boston Globe - Getty Images

2021: UN Cop26 Summit

The actor jetted off to Glasgow to lend his starpower to the 2021 United Nations Climate Change Summit, AKA Cop26, which gathered hundreds of world leaders to question and advise them about cutting greenhouse gas emissions by 2030.

cop26 glasgow
Stefan Rousseau - PA Images - Getty Images

2021: A Hard-Hitting Ensemble Cast

DiCaprio and Jennifer Lawrence played the main scientists—and basically the only characters with any sense—in Don’t Look Up. Other incredible cast members included Meryl Streep as the President, Jonah Hill as her son and Chief of Staff, and Cate Blanchett as a TV news host.

dont look up world premiere
Theo Wargo - Getty Images

2022: Supporting the Gordon Parks Foundation

This gala and auction was for the Gordon Parks Foundation, which preserves the works of the renowned photographer and filmmaker. Parks was also one of the first prominent Black Hollywood directors, with credits such as Shaft and The Learning Tree.

the gordon parks foundation dinner
WWD - Getty Images

2023: Courtside with Jeffrey Katzenberg

DiCaprio hasn’t given up on his Lakers all these years later. He still attends games, like this home matchup against the Memphis Grizzlies. He’s joined in a prime courtside spot by film producer and CEO of DreamWorks Animation, Jeffrey Katzenberg.

celebrities at the los angeles lakers game
Kevork Djansezian - Getty Images

2023: 'Killers of the Flower Moon’ At Cannes

DiCaprio's sixth feature film collaboration with Martin Scorsese, Killers of the Flower Moon, has just landed in theaters to critical acclaim. The film dramatizes the real-life Oklahoma murders of several Osage Nation people between 1910 and 1930, after the tribe became wealthy from discovering oil deposits on their land.

red carpet the 76th annual cannes film festival
Gisela Schober - Getty Images

2023: ‘Flower Moon’ Cannes Photocall

Along with DiCaprio, the film also stars Lily Gladstone, Robert De Niro, Jesse Plemons, and Tantoo Cardinal in major roles. DiCaprio plays Enrest Burkhart, a criminal who assisted his uncle William King Hale (De Niro) in perpetrating several murders of prominent Osage Native Americans.

france film festival cannes
LOIC VENANCE - Getty Images

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