The Holiday

Plot

Cast

• Cameron Diaz as Amanda Woods: the owner of a successful production company that specializes in film trailers. A fan of Meyers' work, Diaz signed on after reading parts of the script. Commenting on her decision to play Amanda, Diaz said that her character "was totally relatable to because we've all had these relationships that fail. But I loved the bravery that she displays. She... learns about who she is and opens herself up to possibilities she's never allowed herself to have before. I felt that was such a wonderful message to put out there." Meyers, who envisioned casting her still during the writing process, compared Diaz's performance in the film to Goldie Hawn's, complimenting her adeptness at physical comedy: "It's really hard I think to be that cute and sexy and that funny and that sort of girl-friendly... She seemed absolutely the right choice for a California girl", she commented. In developing her character, Diaz also improvised on set: "There were a few scenes that were written on the page but then Nancy and I fooled around with them a bit. We didn’t want to take it too broad. We wanted it to be believable, so we included realistic moments", she said.
• Kate Winslet as Iris Simpkins: a society columnist, writing for The Daily Telegraph. Winslet was handpicked by Meyers, who wrote all of Iris's lines with Winslet in mind. The character was named Iris after Jude Law's young daughter. A fan of Meyers' previous work on Something's Gotta Give, Winslet, then primarily known for her portrayals in period films, "loved the idea" of playing a contemporary English woman in a romantic comedy, a genre she had not done before. Winslet said she had initially felt "nervous and... scared about trying to be funny" at times, stating that "Jude Law|Jude and I would speak on the telephone a lot before we started shooting, 'Oh my god, they're going to fire us, they're going to recast, what if we don't make them laugh?" In preparing for her role, Winslet watched screwball comedies from the 1940s, such as His Girl Friday and The Philadelphia Story, to study the dialogues and performances.
• Jude Law as Graham Simpkins: Iris' brother, a book editor, "countryside widower", and single father raising his two daughters by himself after his wife's death. Robert Downey Jr. auditioned for the role. Law accepted the role as he was interested in playing a type of character that he had never played on film before. After his appearances in a string of period dramas and science fiction films in the early to mid-2000s, Law found it tricky to approach the contemporary role of Graham. Like Winslet, he felt more vulnerable playing a character who fitted his own look and did not require an accent, a costume or a relocation. Meyers, who was not immediately sure if Law was going to fit into the genre and whose character evolved more during the writing than the others, decided to cast him after a meeting in which they went through the script together. In preparing for his role, Meyers sent him a collection of Clark Gable films to prepare the performance that she wanted in The Holiday.
• Jack Black as Miles Dumont: a Hollywood film composer working with Amanda and an affiliate of her boyfriend, Ethan. Jimmy Fallon auditioned for the role. As with Diaz and Winslet, Meyers specially created the character for Black after watching his performance in the musical comedy film School of Rock. On his cast, Meyers commented that "when I was thinking of this movie I thought he was someone I would like to write a part for and I'm aware he's not Clark Gable, he's not tall dark and handsome, but he's adorable, he's lovable. It's my way of saying this is the right kind of guy, this is what most guys look like if they're lucky, he's so adorable, and why not?" Cast against type, Black felt "flattered a little bit nervous" about Meyers' approach to star in a rom-com, though he eventually agreed to sign on upon learning that he would play opposite Winslet. While he felt it was difficult to find the adorable side in his role, Black appreciated Miles' relationship with music, stating, "I could relate to that Miles was a film composer and I just got done composing my music for my score. So I knew about that world."
• Eli Wallach as Arthur Abbott: Amanda's neighbor, a famous screenwriter from the Golden Age of Hollywood whom Iris befriends. Wallach was 90 years old when The Holiday was filmed. Meyers found him so animated and energetic on the set that she had to remind him several times during filming to slow down, move more slowly, and act more like an older man.