When it comes to superstars that dominated the headlines during the late 1990s to early 2000s, there were no other stars quite as popular as Leonardo DiCaprio and Kate Winslet.
Although both actors had enjoyed a reasonable level of fame before starring alongside one another in 1997’s Titanic, their status within Hollywood and popular culture, as a whole, skyrocketed following the release of the film, which ended up holding the position as the highest grossing film of all time for 12 years (until director James Cameron outdid himself with his sci-fi epic Avatar in 2009).
The 1997 epic romance and disaster film Titanic catapulted Leonardo DiCaprio and Kate Winslet to superstardom (Credit: Paramount Pictures)
To say Titanic took the world by storm would be an understatement. The film instantly became a huge part of popular culture, and it reignited the world’s interest in the tragic catastrophe of the early 20th century.
Most of the film reviews all the way back in 1997 commented on the excellent chemistry between the two stars, with Janet Maslin of The New York Times stating: “Splendid chemistry between the stars, along with much color from the supporting cast and careful foreshadowing from Mr. Cameron, keeps the romance buoyant even after the dread iceberg gets in the way.”
Despite the incredible chemistry between Leonardo DiCaprio and Kate Winslet, the pair would only go on to star in one other film (as of 2023).
The chemistry between Leonardo DiCaprio and Kate Winslet has resulted in several dating rumors, but the two have remained best friends since starring in their first film together (Credit: Lionel Hahn / AbacaUSA / Startraksphoto)
Let’s take a look at both films that star Leonardo DiCaprio and Kate Winslet, and we’ll be filling you in on any other films on the horizon for the two stars.
1. Titanic (1997) – 88% Critics Score, 69% Audience Score on Rotten Tomatoes
One of the highest grossing films of all time, Titanic was a film that has a larger-than-life effect on popular culture when it was released.
Leonardo DiCaprio as Jack Dawson and Kate Winslet as Rose Dewitt Bukater in the 1997 epic romance and disaster film Titanic (Credit: Paramount Pictures)
Directed by James Cameron (who had directed 1984’s The Terminator, 1986’s Aliens, 1991’s Terminator 2: Judgment Day, and 1994’s True Lies up until that point), Titanic was a departure from the sci-fi action and horror films that typified Cameron’s work by 1997. Cameron produced the film after being obsessed with shipwrecks from a young age, seeking to make a film about one of the most famous tragedies of all time.
Although the producers of the film were skeptical of the film’s financial viability (especially since Cameron was known for action and sci-fi films), they gave the project the green light, causing Cameron to spend six months researching the history of the Titanic.
The film combines a fictional tale of romance involving Rose DeWitt Bukater (Kate Winslet) – a 17-year-old upper-class woman from Philadelphia – and Jack Dawson (Leonardo DiCaprio) – a poor orphan from Wisconsin, who wins a pair of third-class tickets to the Titanic in a poker game with accurate historical characters that were on the ship in 1912.
Leonardo DiCaprio as Jack Dawson and Kate Winslet as Rose Dewitt Bukater in the 1997 epic romance and disaster film Titanic (Credit: Paramount Pictures)
Titanic has a split narrative: in modern day, the research vessel Akademik Mstislav Keldysh finds a priceless diamond necklace and discovers it belongs to Rose, who is still alive. They bring Rose to the site of the wreck, and she relays her memories aboard the Titanic, which is where the main focus of the narrative takes place.
How Was Leonardo DiCaprio Cast in Titanic?
James Cameron had a celebrated following among Hollywood professionals up until that point, and many actors were clamoring for an opportunity to work with him.
While casting the role of Jack Dawson, Cameron had initially envisioned River Phoenix would play the role, although he eventually passed from an untimely drug overdose in 1993.
River Phoenix as Danny Pope in the 1988 drama film Running on Empty (Credit: Warner Bros.)
Other high-profile actors were vying for the role, including Matthew McConaughey, Billy Crudup, and Tom Cruise.
Cameron felt as though most of those actors were too old to play the role of the 20-year-old Dawson, and Tom Cruise had an asking price that was too high. Jared Leto was also considered for the role, but he refused to audition for the part.
After being recommended by casting director Mali Finn, Leonardo DiCaprio eventually auditioned for the part, and the rest is history.
Leonardo DiCaprio as Jack Dawson in the 1997 epic romance and disaster film Titanic (Credit: Paramount Pictures)
How Was Kate Winslet Cast in Titanic?
Much like the casting process of DiCaprio as Jack Dawson, James Cameron had considered a handful of actresses for the role of Rose. After offering the role to stars like Gwyneth Paltrow, Reese Witherspoon, Claire Danes, and Winona Ryder, Cameron was surprised to find that none of the actresses wanted the part.
Meanwhile, Winslet had pushed heavily for the role, sending Cameron regular messages from England regarding it and even pleading with Cameron over the phone to get him to cast her as Rose.
Kate Winslet as Rose Dewitt Bukater in the 1997 epic romance and disaster film Titanic (Credit: Paramount Pictures)
Eventually, Cameron abided, and Kate Winslet was cast in the role of Rose.
2. Revolutionary Road (2008) – 67% Critics Score, 71% Audience Score on Rotten Tomatoes
Despite being lauded for their onscreen chemistry in Titanic, it would take over a decade for Leonardo DiCaprio and Kate Winslet to share the screen once more.
This time, British director Sam Mendes (Winslet’s then-husband) helmed the film, an adaptation of the 1961 novel of the same name by Richard Yates.
Kate Winslet as April Wheeler and Leonardo DiCaprio as Frank Wheeler in the 2008 romantic drama film Revolutionary Road (Credit: Paramount Vantage)
Revolutionary Road was in development shortly after the book was published, but it was stalled for decades until screenwriter Justin Haythe was hired by the BBC to rewrite the screenplay for the film.
Winslet instantly connected with the screenplay and pushed her then-husband Sam Mendes to direct the film with her in the starring role of April Wheeler.
She then shared the screenplay with Leonardo DiCaprio, whom she envisioned to play the co-lead of Frank Wheeler. DiCaprio was impressed with the realism of the portrayal of the flawed marriage between Frank and April and enjoyed the setting of the 1950s, causing him to sign on to the film.
Revolutionary Road tells the story of married couple Frank and April Wheeler, a pair of newlyweds, who purchase a house in suburban Connecticut to start their new lives together.
April is an aspiring actress, while Frank works as a salesman for a machinery business. However, after struggles with their professional and personal lives arise, their marriage starts to turn sour.
Kate Winslet as April Wheeler and Leonardo DiCaprio as Frank Wheeler in the 2008 romantic drama film Revolutionary Road (Credit: Paramount Vantage)
The film received a generally positive critical reception from audiences and critics alike, with famous film critic Roger Ebert deeming DiCaprio and Winslet’s performances as “so good they stop being actors and become the people I grew up around.”
Are There Any Leonardo DiCaprio and Kate Winslet Films in the Future?
As of early 2023, there seem to be no future films in the works for Leonardo DiCaprio and Kate Winslet together. DiCaprio is starring in Martin Scorsese’s upcoming Killers of the Flower Moon, which is set to be released sometime in 2023.
Kate Winslet, on the other hand, is set to star in Lee, a biographical film centering around the life of Lee Miller, an established war journalist. She is also set to collaborate with James Cameron once again in Avatar 3, reprising her role as Ronal, the wife of reef clan chieftain Tonowari (played by Cliff Curtis).
The two powerhouse actors remain best friends to this day, and everyone eagerly anticipates the next time they will be seen on screen again (Credit: Sol Jones / INFphoto)
We hope to see more Kate Winslet and Leonardo DiCaprio performances in the future!