I clearly remember watching the 2006 rom-com “The Holiday” for the first time, not expecting much more than another in a long line of agreeable but often interchangeable romantic comedies.
It would be a nice, but surely forgettable, two-hour escape using the familiar formula: two people meet-cute, fall for each and face obstacles that lead to a “grand gesture” to help them live happily ever.
I was wrong – “The Holiday” is a memorable rom-com that I get more emotionally involved in each time I watch it.
It’s a combination of the great cast (Cameron Diaz, Kate Winslet, Jack Black, Jude Law and Eli Wallach – all who have never been more charming on film), relatable characters (we’ve all gone through the same things), a delightful comic touch, a few twists on rom-com tropes and the sense of joy that permeates this deeply emotional film.
The holiday of the title not only refers to the vacations the two female characters take, but also celebrations of Hanukkah – often forgotten in holiday films – along with Christmas and New Year’s Eve. That’s why I chose this favorite rom-com to be part of the Happy Holidays blogathon hosted by the Pure Entertainment Preservation Society.
But the reason the film is so memorable for me goes deeper. I am in love with “The Holiday” because it is unabashedly in love with love – be it romantic love, family love or the love of friends – and (sit down for this one) it is deeply in love with classic movies.
It’s not simply that writer and director Nancy Meyers has an old black and white movie playing in the background (plenty of films do that) or throws out classic film references at a quick clip. It’s how she weaved the movies from the Golden Age of Hollywood into the fabric of her script. You can’t separate the two and have the same movie.
First, a little about the story.
* * * * * *
Cameron Diaz and Kate Winslet play two disparate women – one in Los Angeles and one in England – who swap houses right before the holidays to mend their broken hearts. Despite their differences in temperament and lifestyles (Iris lives in a cozy cottage in the quaint English countryside; Amanda has a massive, sterile house in busy L.A.) they have similar problems, including long-time heartache.
“I suppose I love more than anyone should,” the forlorn Iris says in the introductory voice-over.
Iris (Winslet) writes wedding announcements at a British newspaper where she has been in love with her co-worker Jasper (the charming Rufus Sewell) for three years, a time she describes as the “darkest days” of her life. Jasper keeps her on string that he won’t pull close nor cut so she can get on with her life.

When the announcement of his engagement is made in their office, the camera zooms in on her face and we see the air go out of her. Her pain is palpable. We are heartbroken because we’ve been there, too.
In Los Angeles, Amanda (Diaz), the owner of a company that makes movie trailers, is flinging shoes at her boyfriend (Ed Burns) and accusing him of cheating. Unlike Iris, Amanda stands up for herself with a confident fierceness and gets him to admit to his infidelity in a scene played with comic undertones. Good for her. But perhaps she’s a little too emotionally strong. No matter how much she tries, Amanda hasn’t cried since her parents split up when she was 15.
“You’re the only woman in the world who breaks up with your boyfriend and doesn’t shed a tear,” he says, an important point of the film.
Those introductory scenes of the two women lead them to make last-minute decision to exchange houses (and continents) for the holidays. Iris quickly blossoms in the California sunshine, but Amanda is not warming up to the English winter and is ready to leave after only six hours. (Perhaps if she left her fancy heels at home, she could traverse the snow easier.)

Good thing for Amanda that Graham (Jude Law), Iris’ handsome brother, shows up a bit drunk at his sister’s house. Though Amanda and Graham are clearly smitten with each other, they try to flirt away their instant connection.
And it’s a good thing for Iris that she meets not one, but two men in California – the funny and self-deprecating film composer Miles (Jack Black) and the elderly neighbor Arthur Abbott (Eli Wallach), a former Hollywood screenwriter with an Oscar on his desk. (His friends wrote “Casablanca,” but he added the word “kid” to the end of the famous sentence – as in “Here’s looking at you…”.)

I love the chemistry between all the characters and not only the romantic chemistry between Diaz and Law (a smoldering love at first sight) or Winslet and Black (who take their time with a chaste, old-fashioned approach), but also between Winslet and Wallach and Black and Wallach. I want to hug them all.
It’s wonderful to watch this group of five pick up on the loneliness in each other and do what they can to help. For Arthur, that means talking to Iris about being the “leading lady in her life” and giving her a list of classic movies to watch to realize her potential (it involves that old-fashioned word “gumption”).
Iris returns the favor by convincing Arthur to accept an award from the Writer’s Guild that leads to one of the film’s most touching moments.
For Amanda and Graham, that means being open to each other no matter how impossible it may seem.
Like any rom-com, we know where this is going. But while there are a few roll-your-eyes moments (when Iris and Amanda each dance around the house, for starters), Meyers takes the characters to unexpected places along the journey.
Part of that is certainly because Meyers imbues her film with so many qualities from another cinematic era that “The Holiday” will naturally feel different. In an interview, Diaz said the film “is contemporary but has a feeling of timelessness.”
Classic films inspired Meyers in fashion, acting and writing. Much of the writing hearkens back to the dialogue of films like “The Philadelphia Story.”
In the DVD commentary, Meyers says she wanted Cameron Diaz to have a physical performance like that of Carole Lombard in “Nothing Sacred.” Hence, you’ll see Diaz, who has great comic timing, decking her soon-to-be ex and jumping up and down in nervous energy. The white pajamas she wears in the opening scene are inspired by films of the 1930s in which “women always wore white satin pajamas,” Meyers explains.
Meyers also talked to Law about watching Cary Grant movies to see how he elevated his leading ladies.
A fan of filmmaker Claude LeLouche, Meyers created a scene reminiscent of a 1960s love montage by having Amanda and Graham playfully hug, kiss and run around outside a grand British manor.
She dressed the set for Arthur’s home office with a wall display of hats like Billy Wilder wore; and there are pictures of the Oscar-winning writer and director on the wall. The room feels like it’s from another era.
The cast was inspired by the classics as well. When Jude Law read the initial meeting between Amanda and Graham, it reminded him of the scene from “Some Like It Hot’ where Marilyn Monroe kisses Tony Curtis, who needs some convincing. The cast watched the film and used it as a reference for the first kiss between Amanda and Graham which is quietly sensual and beautiful.

The script is littered with movie references. There is talk of Irene Dunne (“She’s got gumption.”) and “The Lady Eve” (“Barbara Stanwyck is dazzling and she’s so sure of herself.”) and I love how those films allow Iris to look within herself for strength.
“Every movie that he has told me to see has a powerhouse woman in it,” she realizes about Arthur.
The scene where Arthur walks into a full theater to a standing ovation will resonate with those of us lucky enough to have been in similar circumstances at an event like the TCM Film Festival where we’ve seen that joyous look on a star surprised by a warm reception.
* * * * * *
I’ve focused a lot on classics, but there are modern film references as well. Meyers cleverly uses the phrase “meet-cute” to advance the story. After Iris finds a confused Arthur walking in the neighborhood and delivers him home, he tells her they had a meet-cute and explains the phrase to her.
Having Jack Black play a film composer allows his improvisational talents to shine in the fantastically funny video store scene (remember those) as he picks movies off the shelf and performs their themes for Iris. “Two notes and you’ve got a villain,” he says about “Jaws.” But when he starts messing with “The Graduate,” bystander Dustin Hoffman doesn’t appear too pleased!
Comedy, joy, heartache, heartwarming – you’ll feel a range of emotions in “The Holiday.” (Just wait until Jude Law cries.)
Yet it’s easy for me to distill my love for “The Holiday” down to one moment in the film. On the way to the awards show, Arthur gives Iris a wrist corsage because that’s what was in fashion the last time he went out with a woman.
“If it’s corny, if it’s gonna ruin your outfit, you don’t have to wear it,” he tells her.
“I like corny. I’m looking for corny in my life,” Iris replies.
I am, too.

Watch list
A partial list of classic movie references in “The Holiday.”
“Bluebeard’s Eighth Wife.” The scene in this movie where Gary Cooper only wants to buy the top of a pair of pajamas and Claudette Colbert offers to buy the bottom is referenced in “The Holiday” to help Arthur explain a “meet-cute” to Iris. This 1938 comedy is directed by Ernst Lubitsch.
“His Girl Friday.” Howard Hawks’ 1940 screwball comedy stars Cary Grant as a newspaper editor trying to stop his ex-wife and investigative reporter (Rosalind Russell) from remarrying.
“The Lady Eve.” This 1941 Preston Sturges comedy finds a con artist (Barbara Stanwyck) falling for her mark (Henry Fonda) on board an ocean liner.
“Nothing Sacred.” A woman (Carole Lombard) who thought she was dying, pretends to be sick when a desperate reporter (Fredric March) shows up for a story in this 1937 film.
“Some Like it Hot.” After witnessing a murder, Tony Curtis and Jack Lemmon hide out in drag among an all-female band where they are tempted by beautiful women, including Marilyn Monroe in Billy Wilder’s 1959 comedy.
I love this film so much! When I first saw it I felt so understood, like they made it with people like me in mind. I love that you love it, too, and your review made me want to watch it again immediately! I also really liked that you added the watch list at the end.
LikeLike
Thank you so much for reading! I’m happy to find another fan of this underappreciated movie and that my story made you want to watch it again. Thank you.
Toni
LikeLiked by 1 person
Sold! Same old-same-old I thought when this movie was released. I should have been more diligent.
On the other hand, I think movies/books, etc. come into your life at the right time. The right time may be now. And the right messenger was you! Thanks.
– Caftan Woman
LikeLike
Thank you. I love your point about how movies, etc. come into our lives at the right time – that is so true. I’m humbled that my story may help you discover a film. It was an easy film to overlook – I didn’t see it until a while after it left theaters and wasn’t expecting much at all. I think it a jewel for classic film fans – even just for Eli Wallach. I love watching his character talk about about “old Hollywood.” I learned he also told his own personal stories on the set about his earlier days in Hollywood. I would have loved to have heard those! Thank you again so much for reading.
Toni
LikeLike
I have never had the desire to see this film until now. Thanks for the introduction – I was thrilled to learn about all the classic movie references it has. Thank you in advance! 🙂
LikeLike
Such a lovingly written review of one of my personal favorites. You even managed to share a few things that I didn’t know before, especially regarding the inspiration of how Meyers created and filmed certain scenes. Thank you for sharing your love for this movie.
LikeLike
This movie has also become one of my altimeter favorites — mostly for the same reasons you mentioned. I had memories of Eli wallach playing bed guy roles when I was a youngster and was thrilled to see this side of him. He almost became the glue that held everybody else together! I’ve been trying to find info on all of the celebrities that combined together as the audience in the tribute to Arthur Abbott night. They did this with no screen credits so I figured they appreciated the film — and perhaps the performance of Eli Wallach. That segment was as touching in my mind as most of the other touching moments between the four stars. Films this good don’t happen often and are much appreciated!
LikeLike
Thank you, Phylis. I didn’t know that about the celebrities who were in the tribute scene. Thanks for sharing that with me – it’s another reason to love this film.
Toni
LikeLike