Leonardo DiCaprio's Brilliant Journey To Becoming A Hollywood Leading Man

A once in a generation actor, Leonardo DiCaprio has been one of the biggest names in Hollywood since his debut at a young age. It's difficult to rank all his films and incredible performances, but a few highlights include playing a charming con-man in "Catch Me If You Can" and a drug-fueled stock broker in "The Wolf of Wall Street," directed by the legendary Martin Scorsese. DiCaprio teamed up once again with the director for the 2023 film "Killers of the Flower Moon." The massive project, costing upwards of over $200 million, also linked DiCaprio up with Robert De Niro. In his personal life, DiCaprio has linked up with numerous celebrities, or made waves when not in a relationship. Amazingly, he's also had multiple near-death experiences. As he shared on "The Ellen DeGeneres Show," he was once in a skydiving incident with two failed parachutes and an emergency plane landing on the way to Russia.

Way back in the '90s, an interviewer asked the young actor whether he thought he would one day be famous enough for someone to make a biography about his life. "I can't tell you how it's gonna be in the future because I have no idea. As long as I remain sane, I'm gonna keep doing this kind of stuff," he told i-D. This is how Leonardo DiCaprio transformed from a child to a middle-aged Hollywood icon.

What it was like to grow up as Leonardo DiCaprio

While many aspiring actors have to leave their hometowns behind and make the big trek out to Hollywood to pursue their dreams, that was not the case for Leonardo Wilhelm DiCaprio. Arriving on November 11, 1974, DiCaprio grew up in the Los Angeles neighborhoods of Echo Park and Los Feliz. He has one sibling, a stepbrother named Adam Farrar. "I loved having a little brother, and we got along really well," Farrar told the Daily Mail. As for DiCaprio's first name, his parents were inspired by a celebrity from a different era: Renaissance man Leonardo da Vinci. According to DiCaprio, his parents were in Italy for their honeymoon and visited the world famous art museum Uffizi Gallery in Florence. As the Oscar winner once shared with NPR, "They were looking at a da Vinci painting, and allegedly I started kicking furiously while my mother was pregnant. And my father took that as a sign, and I suppose DiCaprio wasn't that far from da Vinci."

It always seemed clear that DiCaprio was destined to become an entertainer. "The earliest memories I have are jumping up onstage before concerts in downtown L.A. and trying to get on the mic and break-dance, or do imitations of my mother's friends or my father's friends, or be a comic in class," he shared in Esquire.

Inside Leonardo DiCaprio's relationship with his parents

Leonardo DiCaprio is the child of George DiCaprio, a writer and comic artist of Italian descent from New York City, and Irmelin DiCaprio, a secretary who was born and raised in Germany. About a decade before the birth of Leonardo, the senior DiCaprios met in New York City at college. The relationship didn't last and when Leonardo was about a year old, George and Irmelin separated. Both of his parents stayed close to each other and in fact never divorced. The future actor would split time with both while growing up and each played active parts of helping Leonardo early in his career. As noted in a The New York Times Magazine profile, George would read prospective scripts for his son. Meanwhile, his mother helped him with the logistical side of things.

As he was becoming a big star, Leonardo credited his family as a reason for his success in show business. "My parents are so a part of my life that they're like my legs or something," he once said in Vanity Fair. After winning the Academy Award for Best Actor in 2016, DiCaprio invited both his parents and their partners for a celebratory dinner in Los Angeles.

Leonardo DiCaprio had big goals early on

It became obvious early in his life that Leonardo DiCaprio strived for adventure and an alternative career path. "I was the most insane child you can imagine, pretty intolerable to be around. High-octane energy all the time, never wanting to focus on schoolwork," the A-lister recalled to Esquire. Both his parents remember their boy striving for greatness, which they thought at first would be him becoming a professional painter. "We think he's actually an alien, wired a different way than us. There's something going on in him that we don't understand," dad George DiCaprio told The New York Times Magazine. 

By the time he was a junior at John Marshall High School in the Los Feliz neighborhood of Los Angeles, Leo decided to focus all his attention on becoming a star. He dropped out, began taking acting classes, and never looked back. "Leo is on a quest to find out how many things he can do in life and not do them straight," his dad said in NYT Magazine. The actor eventually completed his schooling and earned a GED.

He got his start acting in a kids' show and commercials

Leonardo DiCaprio's career can be partially credited to his older step brother Adam Farrar, who began acting at a young age in commercials. He even had a role in the original "Battlestar Galactica" series. "Leo saw what I was doing and that's what got him interested in acting. He hated school and when he saw I was making good money and you could be schooled on set, he asked if he could do it too," Farrar told the Daily Mail. So, when Leonardo DiCaprio was only five years old, he went for his first acting gig on the children's TV series "Romper Room." Surprisingly, given DiCaprio's future success, producers fired the young boy from the series for supposed misbehavior, according to People.

DiCaprio then followed in the footsteps of Farrar and landed an acting role at the age of 14. "My first role was a Matchbox car commercial. I played a little gangster, slicked back hair," he once recalled to reporters, per InStyle. Admittedly, DiCaprio remembers being nervous during production and understood the power of remembering the scripted lines. "Just get that over with because once you learn your lines, then you can kind of settle into all the other moments in the scene. That's the other piece of advice I give actors," DiCaprio added. He went on to appear in other commercials for brands like Kraft and Bubble Yum, as seen in a YouTube compilation.

How Leonardo DiCaprio crossed paths early on with another star

The first role that earned Leonardo DiCaprio wider recognition was as an unhoused boy on the TV sitcom "Growing Pains." Series star Alan Thicke recalled how impressed he was with the unknown actor. "He just lit up the place," Thicke told People in 1998. The veteran actor even tried to convince the show's producers to give the young man a bigger role on the series, but that didn't come to fruition. Even so, Thicke wasn't worried about DiCaprio's next moves. "We had the sense then that nothing was ever going to stop him," Thicke added. In an incredible coincidence, "Growing Pains" also served as a resume point for another future acting superstar, Brad Pitt, who appeared a few years earlier on the show. The two never did a scene together in the series but were both later in the movie "Once Upon a Time... in Hollywood" together. Looking back at his time on "Growing Pains" on an episode of "Today," DiCaprio was understandably a little fuzzy on the details. "I mean, we're talking decades ago," he noted. 

Early in his career, DiCaprio also remembered running into another child acting star and his hero at the time, River Phoenix. When DiCaprio was 18, he spotted Phoenix at a Halloween party. Sadly, that would be the last time he saw Phoenix. "Before I got a chance to say hello, he was gone, driving off to the Viper Room, where he fell over and died," DiCaprio told Esquire.

He secured movie roles in the '90s

Every actor has to start from somewhere, even the biggest in the biz like Leonard DiCaprio. He made his acting debut in the 1991 film "Critters 3" and just turned 17 at the time of its direct to video release in December 1991. While the movie certainly didn't win any awards, it didn't ruin the young actor's hopes. In fact, he was so good in auditions for the film "This Boy's Life" that his co-star Robert De Niro reportedly selected DiCaprio to join the production. Next, DiCaprio landed his breakout role in the 1993 film "What's Eating Gilbert Grape." For his performance in the movie as Arnie Grape, a young man with a cognitive disability, DiCaprio earned an Academy Award nomination for Best Supporting Actor. According to People, DiCaprio's co-star Johnny Depp said he was less than friendly to the Oscar nominee when they worked together. "It was a hard time for me, that film, for some reason," Depp told reporters at the Santa Barbara International Film Festival. "I tortured him."

After "Gilbert Grape," DiCaprio snagged roles in films like "The Basketball Diaries" and "Total Eclipse." Still, even though his career took off when he was a kid, DiCaprio still faced difficult periods in the industry. "There was a lot of rejection early on ... there was always an element of me that needed to prove something to myself," he once said in Esquire. "It's something I don't want to get rid of, because it's what drives me."

Wherefore art thou Leonardo DiCaprio?

Similar to how Australian director Baz Luhrmann helped turn Austin Butler into a leading Hollywood man, Leonardo DiCaprio worked with Luhrmann in his adaptation of William Shakespeare's "Romeo and Juliet." The 1996 film "Romeo + Juliet" featured DiCaprio and Claire Danes as the two star-crossed lovers. Luhrmann first brought DiCaprio to Australia and convinced him to join the project for a low salary. "Most of the movies I do, I don't get paid a lot of money," DiCaprio told Entertainment Weekly. Perhaps he should have asked for some more cash as production in Mexico came with several unexpected moments, like when DiCaprio became food sick. This was the least of DiCaprio's worries, evidently. "There were a couple murders, one of our people got kidnapped. It was hard and everyone got really sick," the actor recalled to i-D. Upon release, the movie added to his appeal as a heartthrob but also to his mysterious personal life. "I spent four months with him and couldn't figure him out," Danes said in Vanity Fair in 1998.

Many years later, DiCaprio and Luhrmann teamed up again for the big screen adaptation of "The Great Gatsby" in 2013. "It was a very daunting task and I don't know if I would have ventured into it had I not had two incredibly close allies in Baz Luhrmann, who directed me in 'Romeo + Juliet' 18 years ago, and Tobey Maguire, whom I virtually grew up with," DiCaprio told the Mirror.

From a sinking ship to a rising star for Leonardo DiCaprio

The 1997 blockbuster "Titanic" catapulted Leonardo DiCaprio to the top of the A-list. Amazingly, the actor almost didn't take the part. "He didn't want to do a leading man," director James Cameron told People. "I had to really twist his arm to be in the movie. He didn't want to do it. He thought it was boring." Clearly, listening to Cameron worked out: The movie smashed records, remaining the highest-grossing film ever for more than two decades while creating an unprecedented highlight in the careers of DiCaprio and his co-star Kate Winslet.

Understandably, DiCaprio couldn't have predicted how much his life would change as a result of the film, especially in terms of his celebrity status. "I didn't know what being somebody that recognizable entailed. I didn't know what it meant," he once said in Rolling Stone. "And 'Titanic' is something that will never happen again. Nor will I ever try to repeat it."

After the shipwreck drama, DiCaprio and Winslet reunited as on screen lovers in the 2008 film "Revolutionary Road." Through relationships, heartbreaks, and even a pandemic, nothing could come in the way of these two actors. "He's my friend, my really close friend," Winslet once said in The Guardian. "We're bonded for life." DiCaprio shares a similar sentiment, telling Esquire, "Kate Winslet is one of my dearest friends.

Leonardo DiCaprio made a name for himself as an environmentalist

Once Leonardo DiCaprio became an A-lister, he started to dedicate his time and resources to more than acting. When he was only 24 years old, he created the Leonardo DiCaprio Foundation. The mission of his organization was to protect the environment. As DiCaprio grew in popularity, he continued to support charitable causes closest to him. Like the time he threw his birthday party in 2013 and raised $3 million for his foundation, according to Page Six. The United Nations even named him as one of its Messengers of Peace for his work with environmental conservation.

Part of DiCaprio's mission was bringing focus to endangered animals, like working with the Nature & Culture International organization. In 2023, a new species of snake found in Panama earned the nickname "DiCaprio's snail-eating snake." The technical name of the species is Sibon irmelindicaprioae, which the actor proposed because it contains "Irmelin DiCaprio," his mom's name, ABC7 reported. For the Leonardo DiCaprio Foundation, the actor held an auction to bring funds to protecting animals like sharks, which he felt was an underrepresented part of philanthropic efforts, he explained on "The Ellen DeGeneres Show." DiCaprio also admitted he was afraid of sharks and amazingly survived an incident while scuba diving where a great white shark briefly entered his cage. He clarified that while he has no intentions to swim with sharks again, "the work that they're doing is great. They're protecting sharks."

The wild side of Leonardo DiCaprio

"Titanic" turned Leonardo DiCaprio into a heartthrob for teens around the world. While of course great for his career, DiCaprio admitted his performance as the valiant Jack Dawson was then tied to people's opinion of him. "So I set up everything in my personal life to rebel against that image in order to strip it down," DiCaprio explained to Esquire. "I had a lot of fun stripping it down." He became the leader of the P***y Posse, a group of party-loving dudes that included fellow actors Toby Maguire and Lukas Haas, magician David Blaine, and director Harmony Korine. His birthday soiree guest lists typically feature a whole lot of models, and when it comes time to unwind? DiCaprio takes to the high seas on yachts with — you guessed it — models. And he shows no signs of slowing down. When DiCaprio came up on a 2023 episode of "The Drew Barrymore Show," the host quipped, "I love that he's still clubbing."

In his personal life, DiCaprio is said to have a few unique hobbies, such as his interest in dinosaur bones. As noted by Artnet, he's even shelled out major dough on fossils. There is also the unconfirmed rumor that he supposedly wears headphones during sex so he can listen to MGMT's "Electric Feel." Naturally, the celeb gossip Instagram account DeuxMoi combined these two pieces of Leo DiCaprio lore and gave him the nickname "Headphone Dino Bones."

Details of Leonardo DiCaprio's relationship with Gisele Bundchen

Fans were shocked to find out when Gisele Bündchen and Tom Brady finalized their divorce in 2022. For Bündchen, this wasn't the first time she had to deal with a very public breakup with a star. In 2005, she and Leonardo DiCaprio split after dating for about five years. It was that very same year where things appeared to be going well between the two celebrities: DiCaprio attended the 2005 Academy Award ceremonies with Bündchen as his date. In his history at the Oscar ceremonies, this was the only time DiCaprio brought anyone other than his mom. The two first connected in 1999 after DiCaprio was understandably drawn to her during a runway show.

Their breakup came during a transformation time for Bündchen, who had been struggling with panic attacks and anxiety for years. She told People that as she began to make significant life changes, she realized her relationship with DiCaprio no longer worked for her — though she doesn't regret their time together.  "Everyone who crosses our path is a teacher, they come into our lives to show us something about ourselves," she explained. "And I think that's what he was. What is good versus bad? I honor him for what he was." Bündchen told Vanity Fair in 2009 that she still spoke with DiCaprio and stayed friends with his mom.

Leonardo DiCaprio's favorite Bar

Moving into his early 30s, Leonardo DiCaprio was enjoying an evening of music when he unexpectedly found a romantic collection. Between the end of 2005 and the early part of the new year, DiCaprio reportedly first met Bar Refaeli, the Israeli model and business woman, at a party for the band U2. By the spring of 2006, the couple was spotted in Paris. "They were very close to each other. They seemed to enjoy being together very much," a source told People. Their romance appeared to only grow stronger in the following years. In a 2010 interview with Le Matin (via People), DiCaprio revealed he hoped to one day be a father but also explained, "I've no desire to rush." He was still rather close-lipped about his relationship with Refaeli, a choice he said modeled one of his role models, Robert De Niro. "Being discreet in his private life has allowed him to be even more credible in different roles on the big screen," DiCaprio said about De Niro.

Ultimately, DiCaprio and Refaeli split for good in 2011. Years later, details of the relationship came back to haunt Refaeli, who was convicted for tax evasion in Israel. For example, she claimed to live with DiCaprio in 2006 as her primary residence, a lie investigators said was to avoid paying taxes in Israel, per the AP.

What Leonardo DiCaprio thinks about his biggest directors

Leonardo DiCaprio knew what it was like to work with the best, starting very early in his career, appearing with Meryl Streep and Diane Keaton in the 1996 film "Marvin's Room." He has also been directed by an impressive number of famous directors. First, DiCaprio appeared in the 1995 film "The Quick and the Dead" directed by "Evil Dead" creator Sam Raimi. (Raimi, of course, also directed the Toby McGuire era of "Spider-Man" films, a role that DiCaprio apparently turned down.) Then, he teamed up with James Cameron on "Titanic," Martin Scorsese on "Gangs of New York," and Steven Spielberg on "Catch Me If You Can." The actor praised all three filmmakers for their different but effective work in the director chair.  "Jim knows exactly what he wants ... I remember sitting in a theater after it was done and being in awe," DiCaprio said of "Titanic." As for the other two directors, DiCaprio said, "the only other person who knows as much about film as Martin Scorsese is Steven Spielberg."

DiCaprio's also been in films helmed by Ridley Scott, Christopher Nolan, Quentin Tarantino, and Clint Eastwood. "I guess you could say I target most of the directors I want to work with," DiCaprio told USA Today.

Filming The Revenant was a difficult experience for the actor

After turning 40 in 2014, Leonardo DiCaprio began preparing for the most physically demanding role of his life. The night after director Alejandro G. Iñárritu won Best Picture and Best Director for his film "Birdman," Iñárritu flew to Canada to begin his ambitious next film about a man exploring the savage American wilderness in the early 1800s. Production included intense outdoor shots in remote locations, including frigid temperatures and difficult weather. After filming, the director called everyone involved with the films "survivors," per The New York Times. At the heart of the story was DiCaprio, who went as far as to eat a raw bison liver on screen. The actor grew a beard out for the film, which was usually covered in fake frost. He recalled the makeup process alone took four to five hours every day while filming. "It was just a joy, the whole experience," DiCaprio joked on "The Ellen DeGeneres Show" in 2016. 

Reflecting on the experience after production wrapped, DiCaprio understood why some people associated with the movie quit in the middle of filming. "It was physically grueling for everybody. We had to have this massive crew go to far-off locations and move around all over the high altitudes," he told Wired. He especially remembered the relentless weather and massive battle scenes. While DiCaprio was fortunate to have a heater to sit by between takes, he noted, "every day it was a challenge not to get hypothermia."

Leonardo DiCaprio finally won the biggest award in film

With an impressive career of highlights, it's no surprise that Leonardo DiCaprio has been recognized for numerous acting awards.  He earned his first Oscar nomination when he was 19 years old for his work in "What's Eating Gilbert Grape?" While it's of course a big deal to get a nod at such a young age, there's also baggage that comes along with it. "I really didn't want to win because just the fact you have such an expectation on you at that time, people almost want you to be perfect in everything you do and if you're not then it's almost like "OK get him out of here, he was lucky once and now we're done with him,'" the actor told i-D. DiCaprio ultimately lost to Tommy Lee Jones. His first Best Actor nomination came in 2004 for his performance in "The Aviator," but the award went to Jamie Foxx. He lost again for the 2006 political thriller "Blood Diamond" and once more for the 2013 biographical flick "The Wolf of Wall Street." 

Finally, in 2016, DiCaprio walked away with his first golden statue thanks to his work in "The Revenant." Backstage, the veteran actor was joyful over the award. "I felt very honored, quite frankly. This whole thing has been an amazing experience," he said, according to E! News

DiCaprio scored yet another nomination for his performance in "Once Upon a Time... in Hollywood," but once again, he would leave the award show empty-handed.  

He was in a long-term relationship with Camila Morrone

Before she dated YouTube star Logan Paul, model Nina Agdal was briefly with Leonardo DiCaprio. After the two split, the newly single actor found love in the south of France. While in Cannes for the famous film festival in 2017, DiCaprio first spotted model Camila Morrone during a charity fashion event. By the end of the year, the two appeared to be involved after multiple sightings together. Though the couple didn't publicly announce a relationship, an insider told People in 2019, "Camila is long known as Leo's girlfriend." And apparently, it was relatively serious: The tipster went on to say she'd met his parents. That same year, Morrone and DiCaprio were officially considered boyfriend and girlfriend. Not everyone approved of the relationship, especially those against big age differences. In this case, Morrone was 25 years younger than DiCaprio. 

"I probably would be curious about it too," she said in the Los Angeles Times about dating a much older man. Still, she appeared to be unbothered by the different birth years. "There's so many relationships in Hollywood – and in the history of the world — where people have large age gaps. I just think anyone should be able to date who they want to date," she added. Morrone went on to become an actor herself and vowed to become known as more than just the girlfriend of DiCaprio. By the summer of 2022, the couple split.

The actor has been criticized for dating much younger women

A common theme in Leonardo DiCaprio's relationships is the profession of his love interests. Throughout his career, the actor has been involved with many models, including Amber Valletta, Naomi Campbell, and Gisele Bündchen. And while he's continued to date models, he doesn't date Gen X models anymore. 

In 2012, paparazzi spotted the actor riding bikes with his model girlfriend Erin Heatherton while in New Orleans filming "Django Unchained." At the time, he was 37 and she was 23. Years later, things appeared to be going well between Leonardo DiCaprio and his girlfriend Camila Morrone, especially after spending considerable time together during the height of the COVID-19 pandemic in 2020. Then, months after she turned 25 years old, they reportedly ended things. This only added fuel to the theory/joke about DiCaprio apparently not being able to stay in a relationship with a woman who is over the age of 25. 

In September 2022, DiCaprio reportedly struck something up with Gigi Hadid — who was 27 at the time — but by February 2023, they apparently split. The actor also caused quite a stir in 2023 when he appeared to be linked up with model Eden Polani who was 19 when he was 48. However, according to one of People's sources, the two weren't dating.