3. Rough Start
DiCaprio’s first onscreen appearance was in the children’s TV show Romper Room, but he was fired for being too disruptive.
4. Vitruvian Man
DiCaprio was named after the artist Leonardo da Vinci after his pregnant mother happened to be standing in front of one of da Vinci’s paintings the first time she felt him kick. Good thing she wasn’t standing in front of a Warhol. Andy DiCaprio doesn’t quite have the same ring to it.
5. The One
An only child, Leonardo DiCaprio was raised by a single mother, a German national who worked as a legal secretary.
The casting decisions for the movie Inception completely revolved around Leonardo DiCaprio. Nolan knew that he wanted Leonardo DiCaprio for the role of Cobb, so according to him, “We were just trying to cast the best people I could find for those parts, who felt right around Leo.”
7. The Company You Keep
Leonardo DiCaprio is known for keeping the company of models, but it hasn’t always worked out so well for him. In 2005, a model named Aretha Wilson hit him over the head with a broken bottle at a party, injuring his face. She pled guilty in 2010 and was sentenced to two years in jail.
DiCaprio’s mother’s name was Irmelin Indenbirken, which also sounds exactly like something the Muppet’s Swedish Chef would say. His father’s name was George. Which isn’t nearly as funny.
9. Duh, I Did a Bad Thing, George
When he first started out as an actor, his agent suggested he change his name to Lenny Williams to sound “more American.” He wisely declined, since John Steinbeck had already ruined the name Lenny for everyone.
10. Not-So-Good Vibrations
Although he’s now one of his best friends, when they first met on the set of 1995’s The Basketball Diaries, Mark Wahlberg and Leonardo DiCaprio did not get along.
At the age of 19, DiCaprio was the seventh youngest actor to ever be nominated for an Academy Award for his role in 1994’s What’s Eating Gilbert Grape. It would take nearly two decades for DiCaprio to actually get that golden statuette, though.
12. Book It!
In 1998, DiCaprio donated a roomful of computers and equipment to the Los Feliz Library, which was built on the site of his childhood home.
13. Not So Great
In the early 2000s, DiCaprio was set to play Alexander the Great in an epic directed by Baz Luhrmann, his collaborator on Romeo + Juliet and The Great Gatsby. The project would have also starred Nicole Kidman. However, Oliver Stone released the Colin Farrell vehicle Alexander in 2004, a film that proved nobody wants to watch a three-hour movie about Alexander the Great.
14. The Posse
When DiCaprio partied hard in his early 20s, he rolled with an entourage that included magician David Blaine, actor Tobey Maguire, and writer/director Harmony Korine. The group was nicknamed the “[nickname for female genitalia] Posse,” and their exploits were famously detailed in a New York magazine profile of the actor by writer Nancy Jo Sales.
15. Maybe Next Time
Quentin Tarantino wanted DiCaprio to play the role of the Nazi Colonel Landa in Inglourious Basterds, but DiCaprio said no and the role went to Christoph Waltz, who won his first Oscar for his performance.
16. Worth It
Sharon Stone wanted to act alongside DiCaprio so badly that she footed the entire bill for his salary in the 1995 film The Quick and the Dead. Sadly for her, the movie flopped.
17. A Valuable Skill
DiCaprio was trained how to shoot a gun by Thell Reed, a fast-draw expert who had also trained Brad Pitt, Edward Norton, Val Kilmer, and Russell Crowe.
18. A Complicated Web
DiCaprio was also considered for the titular superhero role in Spider-Man (2002). The role instead went to his childhood friend Tobey Maguire.
19. Orphan Adoption
While filming Blood Diamond in South Africa, DiCaprio “adopted” a South African baby girl that he met at an orphanage. He sends her a cheque once a month and talks on the phone with her regularly.
20. Tip of the Iceberg
DiCaprio dated supermodel Gisele Bundchen for three years, from 2002 to 2005, forcing Tom Brady to win five Super Bowl rings to compensate.
21. Quintessential Modelizer
In addition to Bundchen, DiCaprio has also dated or been rumored to have dated Naomi Campbell, Helena Christensen, Bijou Phillips, Amber Valetta, Eva Herzigova, Bar Rafaeli, Anne Vyalitsyna, Madalina Ghenea, and Erin Heatherton.
22. Heartthrob Woes
DiCaprio was once chased through the Louvre by a gaggle of teen girls shortly after the release of Titanic. Can you blame them?
23. Leo the Prankster
In 2016, Leo spotted his Wolf of Wall Street co-star Jonah Hill on the streets of New York. Leo decided to prank him by running up and pretending to be a crazed fan snapping photographs of Jonah. Jonah looked terrified before he recognized Leo and the two hugged it out, making for some hilarious paparazzi photos.
24. Space Oddity
Leonardo DiCaprio is amongst one of the many celebrities who have signed up with Virgin Galactic for a trip to space and, in 2013, a Russian millionaire paid $1.5 million for the chance to go with him. Hopefully, this maiden voyage turns out better than the last one he took.
DiCaprio has worked with Martin Scorsese on five of his movies; Gangs of New York, The Aviator, The Departed, Shutter Island, and The Wolf of Wall Street. Despite the accumulated acclaim between the two, this series of projects earned DiCaprio exactly zero Oscars.
26. Because He’s Grrrrrreat!
In 2010, DiCaprio donated $1,000,000 to the Wildlife Conservation Society at Russia’s tiger summit. Despite multiple plane delays, DiCaprio persisted on making it to the event, which prompted Vladimir Putin to describe him as a “real man.”
27. The Martian
During an environmental panel discussion with President Barack Obama and climate scientist Katharine Hayhoe, DiCaprio casually mentioned that he signed up to go to Mars. Because when you’re Leonardo DiCaprio, having conversations with Barack Obama about your upcoming trip to Mars is just a standard Tuesday.
28. Chilling with the Pope
In 2016, Leonardo DiCaprio met with Pope Francis to discuss the environment and give him a cheque to go toward “charitable works close to his heart.” DiCaprio also gifted the Pope with a book of artwork, including a recreation of Hieronymous Bosch’s notoriously racy “The Garden of Earthly Delights”—but Leo had an interesting reason behind the gift.
He told the Pontiff that the painting hung in his room as he was growing up, and he saw the dark third panel of the painting as representing what we’re doing to the environment.
DiCaprio owns two homes in New York City and one in Los Angeles. He also purchased a significantly-sized island just off the coast of Belize, which he plans to transform into an eco-friendly vacation resort.
30. You Are What You Eat
DiCaprio broke his vow of vegetarianism on the set of The Revenant after taking a bite of raw bison’s liver. Sounds about as tough as his character.
31. Just Say No
DiCaprio says he has never done drugs. So, to prepare for his role in Wolf of Wall Street, he had to speak to a drug expert. Whatever the expert told him, it must have been graphic, because that Quaalude scene is absolutely unforgettable.
32. My Questions Go On and On
One scene from the film Titanic that has been hotly debated since its release is the one where Rose and Jack are floating in the water, clinging onto only a door. Well, more aptly, Rose clings onto the (seemingly) large door while Jack drowns. For years, fans and interviewers alike have had many questions for DiCaprio, co-star Kate Winslet, and director James Cameron about the door (and why Jack had to die).
After years, DiCaprio finally broke his silence on the subject when he was teased about it by his Once Upon a Time… in Hollywood co-stars Margot Robbie and Brad Pitt…by saying “No comment.” The people need answers, Leo!
33. Caught Up
Bizarrely, Leonardo DiCaprio’s name recently came up in a scandal…implicating the former Malaysian Prime Minister. Najib Razak has been accused of abuse of power, criminal breach of trust and money laundering. DiCaprio has ties to financier Jho Low, who is implicated in the scandal. It’s alleged that Low funded movies like Wolf of Wall Street with laundered money.
For his part, DiCaprio is working with prosecutors to return anything he received from Low during their business partnership.
34. Finally, It’s Happened to Me
It was almost a running joke in Hollywood: Leonardo DiCaprio had been nominated for Best Actor at the Academy Awards three times, for The Aviator, Blood Diamond, and The Wolf of Wall Street, but he’d been snubbed each time. Finally, in 2016, he was nominated for The Revenant, and he won, ending a decade-long losing streak.
35. You Gotta Break Some Eggs…
We hope the win was worth it, as DiCaprio’s time making The Revenant was far from a walk in the park. In fact, DiCaprio was absolutely miserable while making the film. The movie was made in Alberta, Canada, where cast and crew braved freezing temperatures—not to mention wet: DiCaprio filmed scenes where he jumped into an icy river wearing a 50lb. bear pelt.
On top of that, DiCaprio suffered from various viral infections, and the scene where he spits up a projectile of phlegm was actually real. He had the flu that day.
36. Danger Drives Him
Of course, all the danger on the set of The Revenant was nothing compared to DiCaprio’s penchant for real-life danger. In fact, the actor has had a number of near-death experiences. First, there was the great white shark that made it into his cage during a dive in South Africa. Then there was a time he watched as his plane’s engine blew up aboard a Delta Airlines flight (the plane then made an emergency landing).
And then there was the skydiving incident, where not one, but two parachutes came out knotted. Luckily, it was a tandem dive, so his partner was able to untangle the second.
37. The King of the World!
The line “I’m the king of the world!” from Titanic was actually ad-libbed by Leonardo DiCaprio. It was voted as the #4 of “The 100 Greatest Movie Lines” by Premiere in 2007.
38. The 25 Club
Most recently, DiCaprio has been linked to 22-year-old model Camila Morrone. They’ve been criticized for their 20-year age difference, leading many to comment that DiCaprio hasn’t dated a woman over the age of 25…ever. That we know of.
39. Thanks But No Thanks But…I Guess, Okay
Despite—or perhaps because of—his scores of near-death experiences, Leonardo DiCaprio was actually scared to film one of the most memorable scenes in Once Upon a Time… in Hollywood. The film’s stunt coordinator revealed that the actor was reluctant to film with a real flamethrower, but was eventually coaxed into doing it.
40. The Legend of Don’s Plum
In the mid-90s, Leonardo DiCaprio and members of his aforementioned “Posse” made a mysterious film by the name of Don’s Plum. The film featured an ensemble cast that included DiCaprio and Tobey Maguire, and was supposedly about a group of friends talking about life at a diner over the course of one night. Why supposedly?
The film was blocked from release by DiCaprio and Maguire themselves. It’s rumored that the content of the film would’ve damaged the young actors’ reputations. Whenever the film has been uploaded, DiCaprio and Maguire have served cease and desist notices, so it’s been seen by very few people. What’re you hiding, guys?
41. Troublesome and Terrible
Speaking of the aforementioned crudely-named Posse, they had a terrible reputation in the 90s, during their heyday. Wherever they went, they allegedly tried to start fights, were known for being bad tippers, and DiCaprio was said to frequently pelt the paparazzi with grapes and garbage—but that was hardly the worst of their notorious exploits.
42. Bar Brawl
One night, the Posse targeted actress Elizabeth Berkley. When she wouldn’t agree to attend an after-party with them, the immature crew called her home so many times that her boyfriend showed up at the restaurant they were at to confront them. They ended up in a brawl outside, where an unnamed member of the group punched him in the throat before fleeing.