Cutest best friends in Hollywood? Leonardo DiCaprio and Kate Winslet have come a long way since starring in 1997’s Titanic.
The actors forged a friendship while filming the 11-time Oscar-winning movie. DiCaprio played Jack Dawson, who falls in love with Winslet’s Rose DeWitt Bukater, despite being from very different worlds.
The James Cameron-directed drama has become one of the most talked about films of all time, partially because of how much chemistry DiCaprio and Winslet had on camera. (The movie made a whopping $600.7 million in the U.S. in 1997. As of August 2022, it has since made $1.5 billion internationally and $2.2 billion worldwide, according to Variety.)
Meanwhile, off screen, the stars’ dynamic has also intrigued viewers. While Winslet insisted in October 2017 that she “never fancied” the Wolf of Wall Street actor, their red-carpet interactions had fans shipping them for decades.
For example, the twosome turned heads in 2007 when they were spotted mingling at the 64th Annual Golden Globes in Beverly Hills on January 15. One month later, the Avatar: The Way of Water actress and the Shining Girls star reunited at the Vanity Fair Oscar Party in Hollywood.
The following year, the pair reconnected on screen for Revolutionary Road. Winslet and DiCaprio haven’t acted together since, but they have been there for each other’s big milestones.
When Winslet married Ned Rocknroll in December 2012, the Django Unchained actor gave her away, a source exclusively told Us Weekly at the time.
The Mare of Easttown alum, for her part, gave fans a glimpse at her friendship with DiCaprio during an interview with Glamour UK that was published in August 2017.
“Sometimes we do quote the odd Titanic line back and forth to each other,” she confessed. “Because only we can, and we find it really funny.”
After not seeing each other for years amid the coronavirus pandemic and travel restrictions, Winslet told The Guardian in December 2021 how emotional it was seeing DiCaprio again.
“He’s my friend, my really close friend,” she gushed. “We’re bonded for life.”
Cameron, meanwhile, teased how his past relationships with both Winslet and DiCaprio have inspired his work moving forward.
The Canadian filmmaker, who teamed up with the English actress on Avatar 2 and 3, exclusively told Us in February 2019 that it was a “dream” to direct Winslet again.
“I think I just emailed with her a couple days ago,” Cameron told Us of their closeness. “Leo and I collide mostly in the environmental circles because he’s doing a lot of good work around climate change and the environment and sustainability … we’re not collaborating directly but we sort of cross paths all the time in that world.”
He teased that if DiCaprio is willing, it would be a “no-brainer” for him to write another part for the Oscar winner. “I can certainly imagine it happening.”
Scroll down to relive Winselt and DiCaprio’s cutest moments — and sweetest quotes about one another over the years:
DiCaprio and Winslet costarred in the blockbuster smash Titanic. The film earned the Oscar for Best Picture — in addition to 10 other Academy Awards — and remained the highest-grossing film of all time for 12 years until Cameron’s Avatar premiered in 2009. Photo by 20th Century Fox/Paramount/Kobal/Shutterstock
The actors reunited onscreen for the drama Revolutionary Road. “I hadn’t realized how much my chemistry with him since Titanic would still stick,” Winslet told Entertainment Weekly in August. “It’s great to discover we can just slip right into it, like muscle memory.” Bbc/Evamere/Neal Street Prods/Kobal/Shutterstock
The British actress felt uneasy doing sex scenes with DiCaprio during Revolutionary Road while her then-husband, Sam Mendes, directed them from behind the camera. “I just kept saying, ‘This is too weird.’ And Leo was like, ‘Oh, get over it,’” she told Entertainment Weekly in August. “And I’m going, ‘Yeah, a little reminder: You’re my best friend. He’s my husband. This is a bit weird.’” Bbc/Evamere/Neal Street Prods/Kobal/Shutterstock
The former child star and Winslet attended the L.A. premiere of their film Revolutionary Road at the Mann Village Theater in December. “We've been very close for a number of years and we'd been actively looking for something to do together,” DiCaprio told BBC News at the time. “Thank God this came along.” Matt Baron/BEI/Shutterstock
The pals embraced after Winslet won Best Performance by an Actress in a Motion Picture - Drama for Revolutionary Road at the 66th Annual Golden Globe Awards in Beverly Hills in January. Dave Lewis/Shutterstock
“Kate Winslet is one of my dearest friends,” the Inception star gushed during his March Esquire cover story. “We have the ultimate trust in each other.” Alex Berliner/BEI/Shutterstock
"You know, it's been such a long time, but it was such, you know, a huge part of my life," DiCaprio told CBS This Morning in February. "And people maybe think I have a reaction to that film. But the truth is, I'm incredibly proud of it. And not only that, the movie has really made me be in control of my career." Photo by 20th Century Fox/Paramount/Kobal/Shutterstock
"I think the reason that friendship works is because there was never any romantic thing," the Holiday actress explained in Marie Claire UK’s November issue. "It's so disappointing for people to hear that, because in the soap opera of the Kate and Leo story we fell in love at first sight and had a million snogs, but actually we never did. He always saw me as one of the boys. I've never really been a girly-girl." Alex Berliner/BEI/Shutterstock
“She’s my favorite actress in the industry,” DiCaprio told Entertainment Tonight at the Golden Globes in January. The twosome were later spotted sharing an adorable hug after he won Best Performance by an Actor in a Motion Picture for his work in The Revenant. Matt Sayles/Invision/AP/Shutterstock
After DiCaprio added a Screen Actors Guild Award for The Reverent to his resume, Winslet gushed over the actor’s possible awards show sweep. (He was also the front-runner to win the Oscar that year, which he eventually won.) “I think you can sort of feel it, and I think that everyone wants it for him,” the Sense and Sensibility actress told BBC News in January. “It would be amazing.” Bbc/Evamere/Neal Street Prods/Kobal/Shutterstock
Winslet joked in February that her character could have saved DiCaprio’s Jack Dawson from dying in the freezing water. "I think he could have actually fitted on that bit of door," she told Jimmy Kimmel. Mark J Terrill/AP/Shutterstock
"People are always so excited to see Leo and myself in the same space, which at the end of the day, that's so lovely," the Reader actress said during her February appearance on Jimmy Kimmel Live! in February. "It's been 20 years [since Titanic], and people still get such a kick out of it. It's really quite endearing. People still get so overwhelmed with the Jack and Rose thing.” Vince Bucci/Invision/AP/Shutterstock
The former costars reunited at the actor’s annual Leonardo DiCaprio Foundation gala at Domaine Bertaud Belieu in Saint-Tropez in July. In honor of the 20th anniversary of Titanic, they auctioned off a private dinner with themselves to benefit charity. David Fisher/Shutterstock
"You don't even want to know the last conversation we had, because it was so funny and made me laugh so much," the Blackbird actress told Glamour UK in August of her chats with the California native. "We found ourselves saying to each other, 'Can you imagine if the world really knew the stupid things we say?' I'm not going to tell you what we actually talk about, but yeah, we're very, very close." Joanne Davidson/Shutterstock
“For Leo and I, I think it was seven months of very intense work,” Winslet said during an October appearance on ITV’s Lorraine about filming Titanic with DiCaprio. “We were both really very young, and luckily — and this is the fortunate thing — we never fancied each other. I know that’s really annoying to hear, I’m sorry, but we really never did.” She added: “We were able to tease each other, and we still do, so it’s really amazing.” Matt Sayles/AP/Shutterstock
The Mountain Between Us actress confessed she “couldn’t stop crying” after she finally saw the Once Upon a Time in Hollywood actor following a prolonged separation amid the COVID-19 pandemic. “I’ve known him for half my life! It’s not as if I’ve found myself in New York or he’s been in London and there’s been a chance to have dinner or grab a coffee and a catch-up,” Winslet told the Guardian in December. “We haven’t been able to leave our countries. Like so many friendships globally, we’ve missed each other because of COVID.” Jordan Strauss/Invision/AP/Shutterstock
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