The Holiday - Cast

Cast

• Cameron Diaz as Amanda Woods, a Los Angeles trailer editor. A fan of Meyers' work, Diaz signed on after reading parts of the script. Meyers, who envisioned casting her still during the writing process, compared Diaz' performance in the film to Goldie Hawn, 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.
• Kate Winslet as Iris Simpkins, a society column editor for The Daily Telegraph. Winslet was hand-picked by Meyers, who wrote all of Iris' lines with her in mind. A fan of Meyers' previous work on Something's Gotta Give (2003), 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. 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. Portraying a book editor and single father, 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, the actor stated, he felt more vulnerable about 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, sent him a collection of Clark Gable movies to prepare the performance that she wanted in The Holiday.
• Jack Black as Miles Dumont, a music composer and affiliate of Ethan. As with Diaz and Winslet, Meyers specially created the character for Black after watching his performance in the musical comedy film School of Rock (2003). Cast against type, he felt "flattered a little bit nervous" about Meyer's approachal to star in a rom-com, though he eventually agreed to sign on upon learning that he would play opposite Winslet. Meyers described Black as "tremendous fun" on-set.
• Eli Wallach as Arthur Abbott, Amanda's neighbor, whom Iris befriends.
• Shannyn Sossamon as Maggie, Miles' girlfriend and aspiring actress.
• Edward Burns as Ethan Ebbers, Amanda's boyfriend.
• Rufus Sewell as Jasper Bloom, Iris' on-and-off affair.
• Caroline Crimmins as Beatrice, Amanda's co-worker

Extended Simpkins family include Miffy Englefield and Emma Pritchard as Sophie and Olivia, Graham's daughters, respectively. The film also cast Bill Macy as Ernie and Shelley Berman as Norman, friends of Arthur, as well as Kathryn Hahn as Bristol and John Krasinski as Ben, Amanda's employees. Jon Prescott appears as Maggie's short-time affair.

Dustin Hoffman appears in the video rental store in an uncredited cameo as Jack Black talks about the score from The Graduate. According to Hoffman, this was unscripted and unexpected. He was going to Blockbuster for a movie, saw all the light and came over to see what was going on. He knew director Nancy Meyers, who scripted a short scene with him in it. Lindsay Lohan, who had made her motion picture debut in Meyers' remake of The Parent Trap (1998), and James Franco, a friend of Meyers, make uncredited appearances in the trailer of the fictional movie Deception, which Amanda and her team finish at the beginning of The Holiday.