The Nearly 20-Year History of Kate and Leo’s Awards-Season Friendship
From Getty Images.Oscars Red Carpet, 2016
Though they each brought their own dates, Kate and Leo walked the 2016 red carpet arm-in-arm on the way to what many assume will be his first Oscar night victory. It’s enough to make anyone want to stroll down memory lane.
Golden Globes Red Carpet, 1998
Kate and Leo first sparked wishful thinking when, at the tender ages of 23 and 24, respectively, the two attended the Golden Globes as each other’s dates. “Is there something we oughta know?” an interviewer asked with a tonal wink and nudge. “No, absolutely not, absolutely not. We’re good buddies,” Leo responded, not for the last time. DiCaprio, Winslet, and a little film they did called Titanic were all nominated for awards. Unlike Winslet, DiCaprio was not nominated for an Academy Award that year, so while he skipped the awards, Winslet walked the 1998 Oscars red carpet with her soon-to-be first husband, Jim Threapleton, by her side.
SAG Red Carpet, 2005: “I love you, sweetheart.”
But both Kate and Leo were back on the awards circuit with a vengeance in 2005: she for Eternal Sunshine of the Spotless Mind and he for The Aviator. Winslet crashed DiCaprio’s red-carpet interview, saying, “I was told to interrupt,” as Leo joyfully kissed her hello. “She’s the same person she’s always been,” Leo told his interviewer as Kate looked on. “She’s a fantastic human being.” Talk turned to, what else, Titanic, and Winslet said, “So he said I was the best kiss he ever had on-screen but I can tell you right now he hated it and he would complain bitterly.” But Winslet proved her heart was still definitely going on for Leo, saying, “I just feel so proud that you’ve turned into this really special person.” Giving her a friendly kiss, Leo threw fuel on the Jack-and-Rose-forever fire by saying, “I love you, sweetheart.”
Leo Allegedly Gives Kate a Wink at the Oscars, 2005
Later that same year, both attended the Oscars and, according to a popular story circulating among Kate-and-Leo fans, Winslet was nervous when presenting the award for best cinematography and looked for support from DiCaprio in the crowd. “He gave me a big, fat wink and a little, quiet thumbs up. It helped,” an un-sourced Winslet quote reads. We’ve no confirmation this story is true, but it’s too charming to leave out, so here’s an image of Leo winking and video of Winslet presenting. You decide for yourself if it all played out that way or if this similarly not-confirmable 2006 Oscars wink is also just the by-product of overzealous Titanic imaginations.
Awards Season, 2007
Neither Kate nor Leo won any major acting awards in 2007, but they were both nominated aplenty: she for Little Children, he for Blood Diamond and The Departed. Even though this wasn’t their year to take home any golden statues, Winslet and DiCaprio were still by each other’s side at both the Golden Globes (left) and the Oscars (right).
Golden Globes Red Carpet, 2009
Back to reality and the biggest awards night in the history of Kate and Leo’s friendship (so far). The pair were side-by-side again, having both starred in and received nominations for their work as a married couple in Revolutionary Road. Throughout the publicity tour for this film, Leo was bombarded with questions of when he would decide to settle down and have kids and if it was hard to play a married man having no experience with marriage himself. After no doubt hearing him answer the question a thousand times, Kate intervened, saying, “I can step in for you here, if you like.” “Go for it, buddy,” Leo responds. “You know, he’s an actor—he’s a brilliant actor—and he knows about relationships. . . . He gave the best performance he’s ever given in his life.” As you can see, above, Leo was grateful for her intervention.
Kate Wins a Golden Globe for The Reader, 2009
Winslet and DiCaprio sat next to each other at the Revolutionary Road table, but Kate won early on in the evening for her work in another film: The Reader. DiCaprio was on hand to help her tackle her disbelief—“You have to forgive me,” a flustered Winslet would later say during her acceptance speech, “I have a habit of not winning things.” Kate did not thank Leo in this speech. She was saving that up for later.
Kate Wins a Golden Globe for Revolutionary Road, 2009
Winslet picked up her second acting statue of the night for Revolutionary Road and made Titanic lovers’ dreams come true when the visibly ruffled double-winner tearfully gushed, “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. . . . I love you with all my heart, I really do.” The camera caught Leo responding by blowing her a kiss from the audience.
Kate Wins an Oscar for The Reader, 2009
Neither Kate nor Leo received Oscar nominations for their work in Revolutionary Road, but by the time the ceremony rolled around it seemed a given that Winslet would win the best-actress statue for The Reader. She graced the cover of Time with the headline “Best Actress,” and, as she pointed out to Mario Lopez on the red carpet, DiCaprio had given her the necklace she was wearing in the cover photo. So even though Leo didn’t attend the Oscars that year, he still managed to be part of the story of Kate’s first Academy Award victory.
Leo on the Golden Globes Red Carpet, 2016
Fast-forward seven years and it seems all but guaranteed that this is finally DiCaprio’s year to take home an Academy Award. But it’s a long road to Oscar and, lucky us, Kate has been by his side the whole way. They may not be co-stars this year, but Leo and Kate have been friends for nearly 20 years (he walked her down the aisle for her 2012 wedding to Ned Rocknroll). So it should come as no surprise to hear Leo call Kate his “favorite actor.” DiCaprio brought his dad as his date but said Kate was “hanging out with” him that night. “We’re going to go to the after-parties together.”
Kate Greets Leo at the Golden Globes, 2016
Though they sat at different tables, Kate and Leo found some time before the after-party to catch up. Leo, as expected, picked up an award for The Revenant, but Kate surprised some awards-season experts by also picking up a Golden Globe (her fourth) for her work in Steve Jobs. That night, Winslet kick-started her own awards-season narrative and the pair unwittingly launched an awards-laden Titanic reunion that has dominated the 2016 season.
Kate Hugs Leo at the SAG Awards, 2016
Some canny awards-show producer did manage to sit Kate and Leo near each other at the Screen Actors Guild Awards and cameras were ready to catch the friends embracing when Leo won for The Revenant. Winslet didn’t win that night, but shortly after the SAG awards, she explained why attending the Oscars this year was so important to her: “I feel very strongly that it may possibly be Leo’s year. [H]e is my closest friend in the world and I just couldn’t imagine not being there to support him.”
Kate Squeezes Leo’s Hand at the BAFTAs, 2016
Winslet further cemented her own shot at an Oscar earlier this month when she took home the BAFTA for Steve Jobs. Winslet squeezed DiCaprio’s hand as she rushed down the aisle to pick up her award, and later, in the pressroom, DiCaprio called Winslet his “homegirl.” The two were later seen backstage cozied up to each other, clutching their newly won BAFTAs in their hands. Next stop: Oscars.
