•
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. 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 [the comedy] too broad. We wanted it to be believable, so we included realistic moments", she said. 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. 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. and
single father raising his two daughters (Miffy Englefield as Sophie, and Emma Pritchard as Olivia) by himself after his wife's death. 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. 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?" though he eventually agreed to sign on upon learning that he would play opposite Winslet. •
Eli Wallach as Arthur Abbott: Amanda's neighbor, a famous screenwriter from the
Golden Age of Hollywood whom Iris befriends.
Edward Burns appears as Ethan, Amanda's unfaithful composer boyfriend whom she breaks up with in the beginning of the film, while
Rufus Sewell plays Jasper Bloom, Iris's emotionally needy ex-boyfriend.
Shannyn Sossamon plays Maggie, Miles's actress girlfriend. Sewell and Sossamon reunite as they both starred in ''
A Knight's Tale'' (2001) together, although they do not share a scene. 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 (1967). According to Hoffman, this was unscripted and unexpected. He was going to
Blockbuster Video to rent a film when he saw the lighting from the film production crew and walked over to see what was happening. He knew director Nancy Meyers, who scripted a short scene with him in it.
Lindsay Lohan, who had made her
feature film debut in Meyers'
1998 remake of
Disney's 1961 film
The Parent Trap, and
James Franco, a friend of Meyers, make uncredited appearances in the
trailer of the fictional
action film Deception, which Amanda and her team finish at the beginning of
The Holiday.
Alex O'Loughlin and
Odette Yustman play a kissing couple in a fictional film in the opening scene as Miles composes the music for the scene. == Production ==