Red-Carpet Flashback! Kate Winslet and Leonardo DiCaprio Through the Years
- 1/15
The Golden Globe Awards (1998)
Dicaprio was 21 years old and Winslet, 22, when they filmed Titanic. Winslet later told Marie Claire “We needed each other to lean on, because we were very young and working all kinds of crazy, bloody hours, and it was a shock to the system.“ Both were nominated for Golden Globes for their roles and attended the ceremony together on January 18, 1998. (Photo: Getty Images)
- 2/15
The Golden Globe Awards (1998)
The two young stars posed backstage with director James Cameron who won Globes for Best Director and Best Motion Picture, Drama, for Titanic. The film went on to receive the top honor at the Oscars that year, but DiCaprio was famously snubbed in the nominations. (Photo: Jim Smeal/WireImage)
- 3/15
The Golden Globe Awards (2007)
Our favorite duo reunited at the 2007 Golden Globe awards. Winslet was nominated for her performance in Little Children, while Dicaprio received two noms for his roles in The Departed and Blood Diamond. (Photo: Alexandra Wyman/WireImage)
- 4/15
The Academy Awards (2007)
The two pals chatted with Will Smith in the audience of the Oscars on February 25, 2007. Both Winslet and DiCaprio were nominated, though neither took home the statue. (Photo: Mark J. Terrill/AP)
- 5/15
‘Vanity Fair’ Oscar Party (2007)
The pair were seen hanging out after the respective Oscar losses at the famous Vanity Fair party. Back in 1997, DiCaprio told Entertainment Tonight that Winslet is “such a terrific person in general that our chemistry naturally happened on screen. We just like each other as people.” (Photo: Eric Charbonneau/WireImage)
- 6/15
‘Revolutionary Road’ Premiere (2008)
Finally sharing the big screen together again, Winslet and DiCaprio played a troubled married couple in Revolutionary Road. During their press tour, DiCaprio told The Today Show, “She’s still as beautiful and radiant as the day I met her. She is the consummate professional; she keeps pushing herself to an emotional truth when she’s working. That’s why I keep saying she’s the best." (Photo: Steve Granitz/WireImage)
- 7/15
The Golden Globe Awards (2009)
DiCaprio escorted his nominated costar to the 66th Annual Golden Globe Awards held at the Beverly Hilton Hotel on January 11, 2009. (Photo: Frazer Harrison/Getty Images)
- 8/15
The Golden Globe Awards (2009)
During Winslet’s acceptance speech for Best Actress in Revolutionary Road, she proclaimed her love for her pal in the most adorable way. “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.” (Photo: Chris Haston/NBC/Getty Images)
- 9/15
‘Revolutionary Road’ Premiere (2009)
DiCaprio and Winslet attended the London premiere of Revolutionary Road at Odeon Leicester Square on January 18, 2009. (Photo: Mike Marsland/WireImage)
- 10/15
Paramount Pre-Golden Globes Party (2010)
The duo mingled at Paramount’s Pre-Golden Globes party with CEO Brad Grey, and director Martin Scorsese on January 16, 2010 (Photo: Alex J. Berliner/BEI)
- 11/15
The Golden Globe Awards (2012)
On why their friendship has endured, DiCaprio told Oprah Winfrey "In a lot of ways, Kate and I have really grown up in this industry together; we’ve been a support mechanism for each other for such a long period of time. We’ve been there for each other and helped guide each other.” (Photo: Vince Bucci/NBC/Getty Images)
- 12/15
The Golden Globe Awards (2016)
The two besties embraced in the audience after their individual wins for The Revenant and Steve Jobs on Jan. 10. When asked about why she was so surprised that she won that night, Winslet replied, “To be honest with you, because I’ve been so focused on Leo, and him winning everything and being so excited for him.” (Photo: Larry Busacca/NBC/Getty Images)
- 13/15
Screen Actors Guild Awards (2016)
“People are always so excited to see Leo and myself in the same space, which you know at the end of the day that is so lovely, isn’t it,” Winslet recently told Jimmy Kimmel. “It’s been 20 years and people still get such a kick out of it.” (Photo: Larry Busacca/Getty Images)
- 14/15
Screen Actors Guild Awards (2016)
Winslet told Kimmel after the SAG awards “We were giggling about it that night. I was like, ‘Oh my God, can you actually believe it that people still get so overwhelmed by the Jack and Rose thing?” (Photo: Dimitrios Kambouris/Getty Images)
- 15/15
Screen Actors Guild Awards (2016)
Jack and Rose forever! (Photo: Christopher Polk/Getty Images)
Over 18 years ago, Leonardo DiCaprio and Kate Winslet stole our hearts as the ill-fated lovers Jack and Rose in the blockbuster Titanic. Unlike that tragic romance, their friendship has stood the test of time — so has our love for them. The two actors are both nominated for Oscars this year: he, for Best Actor for The Revenant, and she, for Best Supporting Actress for Steve Jobs. So while they’re hitting the awards circuit again, we wanted to take a look back at our favorite pals on the red carpet.