Law and Winslet were new to the genre of romantic comedy. “The way Nancy breaks down the beats of a scene, the timing of a joke or a reveal, is kind of a science,” says Law, who has earned Oscar® nominations in the past for his performances in Cold Mountain and The Talented Mr. Ripley. “It’s hard work, but she makes it look easy.”
Winslet heartily concurs: “Oh yes. The flow and rhythm of Nancy’s writing is incredibly precise.”
The Holiday marked a welcome change of pace for Winslet, who earned her first Academy Award® nomination for Sense and Sensibility. Her 1997 performance in Titanic made her, at age 22, the youngest actress ever to be twice nominated for an Oscar®. She was nominated again for Iris, and then again for Eternal Sunshine of the Spotless Mind. “I’ve spent a lot of time in my career wearing corsets,” she says, “and am proud to be part of a contemporary comedy playing an English person.” Being asked to be funny was another new experience. “The biggest reward for me on this film was to be in the middle of a scene and hear ten people at the video monitor burst out laughing,” she smiles.
But the character of Iris has several facets, all of which Winslet exploited to the fullest. “There were times when Kate brought me to tears,” says Meyers. “She can reveal herself in so many ways, and all of them are honest.”
To complement her two sterling leading ladies, Meyers took great care in choosing their romantic interests. “I wanted Graham to be complicated, but not in the normal way. Hopefully, his issues are unexpected,” she says. “Jude is very right for this part. He is also wonderful with Cameron, and the work he does in this film is quite different from anything I’ve seen him do before.”
The choice of Jack Black to play Miles was more than just a stroke of bold casting on Meyers’ part, she admits. “When I saw Jack in School of Rock, I fell in love with him,” she says. “I wrote this part for him because I adored him so much from that movie. But I never thought he would say yes because it’s a very different role for him – it’s a love story.”
In truth, Black was surprised when he was approached. “When I first heard that Nancy had written a part with me in mind, I thought, really? Have you heard my band Tenacious D?” he laughs, “because I’ve got a lot of raunchy humor in my film history. But Nancy said, ‘I know what you do and I like it.’ So I was like, ‘all right, good, let’s do it.’ I can’t believe I actually got paid to stare at Kate Winslet from really close up and watch her kick-ass acting.”
Meyers cast Amanda and Iris’ ex-boyfriends with similar care, honing in on Edward Burns for Ethan and Rufus Sewell for Jasper. Interestingly, Burns had previously directed and starred opposite Diaz in the romantic comedy She’s the One. In The Holiday, their relationship is far less cordial, however, “Cameron gets to punch me twice,” Burns laughs. “I guess you have to be in really good shape to do a romantic comedy.”
Diaz admits that she was in rare fighting form for her scenes with Burns. “I don’t think I’ve ever had as much fun playing a break-up,” she says. “Eddie was perfect as Ethan – dry and deadpan. I didn’t want our scene to end. But Ethan deserved to be punched in the face. His actions were beyond questionable. They needed to be called out. And, believe me, I called him out.”