By Sara Bright
Jack Black is one of the most versatile and charismatic actors in Hollywood. He can make us laugh with his comedic roles, thrill us with his action-packed performances, and touch us with his dramatic portrayals. He has worked with some of the biggest names in the industry, from Leonardo DiCaprio to Angelina Jolie. But who is his favorite co-star of all time?
The answer might surprise you. It’s not one of his fellow comedians, nor one of his frequent collaborators. It’s none other than Kate Winslet, the Oscar-winning actress who starred with him in the 2006 romantic comedy The Holiday.
In a recent interview with Entertainment Tonight, Black revealed that Winslet was his favorite co-star he ever had, and explained why. “You know what? The first one that comes to mind – and I’m gonna say it just cause it’s the first one that comes to mind,” he said. “Kate Winslet and I’ll tell you why. She was my favorite co-star I’ve ever had because when you look in her eyes, she was like really present,” Black recalled. “I feel like if you look into my eyes, you just see a shadow of a robot,” he added.
The Holiday: A Modern Classic
The Holiday is a film that tells the story of two women, Amanda (Cameron Diaz) and Iris (Winslet), who swap homes for the Christmas holidays, hoping to escape their romantic troubles. Amanda ends up in a quaint cottage in Surrey, England, where she meets Iris’ brother, Graham (Jude Law), a charming widower and father of two. Iris, on the other hand, stays in Amanda’s luxurious mansion in Los Angeles, where she befriends Arthur (Eli Wallach), a retired screenwriter, and Miles (Black), a friendly music composer.
The film, directed by Nancy Meyers, was a box office hit, grossing over $200 million worldwide. It also received positive reviews from critics and audiences, who praised the chemistry and performances of the four leads, as well as the heartwarming and humorous story. The film has since become a cult favorite, especially during the festive season, and is often ranked among the best Christmas movies of all time.
Jack and Kate: An Unlikely Duo
One of the most appealing aspects of The Holiday is the unlikely pairing of Jack Black and Kate Winslet, who play Miles and Iris, respectively. Black, who is known for his comedic roles in films such as School of Rock and Nacho Libre, and Winslet, who is acclaimed for her dramatic roles in films such as Titanic and The Reader, seem like an odd match on paper. However, on screen, they have a natural and adorable chemistry, as they bond over their love of music, movies, and life.
Black and Winslet have both expressed their admiration and affection for each other, both on and off screen. In a 2006 interview with People, Black said that Winslet was “the best actress of our generation” and that he was “in awe” of her. He also said that he enjoyed working with her, and that they had a lot of fun on set. “She’s hilarious. She’s got a wicked sense of humour,” he said.
Winslet, in turn, said that Black was “a complete revelation” and that he was “so much more than a comic actor”. She also said that he was “a joy” to work with, and that they had a great rapport. “He’s so clever and so quick, and he just made me laugh all the time,” she said.
The Fans’ Wish: A Sequel
Ever since The Holiday came out, fans have been clamoring for a sequel, hoping to see more of the adventures and romance of the four characters. They have also been curious about what happened to Miles and Iris, and whether they stayed together or not. Some have even suggested that a sequel could focus on their children, and how they would inherit their parents’ love of music and movies.
However, despite the fans’ wishes, a sequel has never been confirmed or announced. Meyers, the director, has said that she is not interested in making a sequel, and that she prefers to leave the characters as they are. “I’m very happy with the film and how it turned out,” she said in a 2016 interview with Deadline. “I love the characters and I love the actors who played them, and I feel like it’s a complete piece.”
The actors have also been vague about the possibility of a sequel, although they have not ruled it out completely. In a 2020 interview with Jimmy Fallon, Winslet said that she is recognized more for The Holiday than for Titanic, and that she would be open to reuniting with Black and the rest of the cast. “I would love to do something else with Jack. I would love to do something else with Jude and Cameron, too,” she said.
Black, meanwhile, said that he has not heard anything about a sequel, but that he would be happy to work with Winslet again. “She was my favorite co-star I’ve ever had, and I would love to do another one with her,” he said.





