Review Essay
The Holiday’s a Nancy Meyers film through and through — and if you’re someone who knows those movies (What Women Want; Something’s Gotta Give; the 1990s Father of the Bride reboot films, which she screenwrote), you know a little bit about what you’re in for. Lush interiors, especially really lavishly appointed kitchens; romantic/comedic dialogue that owes a zippy debt to Nora Ephron even if it’s rarely quite as stylishly composed; a willingness to take the emotion of a scene more than a little over the top. This movie hits those marks reliably, and as a result is, to me, both reliably entertaining for a big chunk of its runtime and also a little too artificial and hollow to really land the punches it’s swinging for.
The premise is simple enough — Cameron Diaz’s Amanda and Kate Winslet’s Iris are both on serious rebounds after painful romantic fallouts that have left them questioning their own identities. They find each other via a wonderfully hokey of-its-2006-era home swap website, and agree that Amanda will spend Christmas in a charming Surrey cottage while Iris spends her Christmas in a sprawling SoCal McMansion, buffeted by the Santa Ana winds. They’re hoping not to find love, of course, which is why it’s so convenient when Iris’s brother Graham (played by Jude Law) drops in to find Amanda unexpectedly in residence at the cottage, and when Amanda’s ex’s buddy, Miles (played by a charmingly baby-faced Jack Black), shows up to retrieve some things and encounters an unanticipated English woman on holiday. The rest….well, you know the rest, probably, though there’s a twist or two I won’t reveal.

The film’s at its best when it’s not trying to advance the primary plot, which is Diaz and Law falling in love — two incredibly attractive humans at basically the height of their Hollywood stardom, but underwritten in ways I’ll get to in a moment. The absolute best pairing in the movie, by contrast, is actually Kate Winslet’s Iris and her new neighbor, a frail old screenwriter who was big in the mid-20th Century but now gets lost walking down the street – a man named Arthur, played spiritedly by Eli Wallach, who was 91 at the film’s release. Iris and Arthur are incredible pals, and his not-so-secret desire to lift her self-esteem and make her see herself as a sassy screwball heroine with “gumption” is maybe the sweetest part of the film – both romantic and comedic without being rote. Meyers’s eye for exterior shots, especially in the English countryside, is really excellent, so there’s a lot of cinematic beauty here to enjoy at times when all we’re seeing is establishing shots or montages.
The two main pairings are underserved by the film in different ways. Winslet and Black are honestly very cute together – Miles is a sweet, decent fellow who, when the “Jack Black” within him is dialed down to 85% or lower, is impossible not to like, and Winslet’s character is developed really successfully (I think the emotional richness of the Arthur subplot helps her a ton in this regard, plus Iris is just given a more sympathetic situation in the screenplay to begin with). The problem with their subplot is that it’s given short shrift by a movie that’s more interested in Diaz and Law — Miles and Iris get a couple of really nice scenes together, but that’s about it, and the romance as a result feels a little hasty. The challenge with Amanda and Graham, meanwhile, is connecting with them: Graham’s character has the biggest twist, and while the revelation we get about him really adds substance to his character, it’s also hard to reconcile all the pieces of the guy we’ve been introduced to with the person he apparently is? Jude Law is, again, so hot in 2006 that even this straight dude can appreciate the man’s cheekbones, but in some ways that makes him harder to see as anything but a movie star in the spotlight. And poor Cameron Diaz is handed, in Amanda, a character who never really feels like a person to me — she’s all screenwriting quirks and problems, and most of the moments that are meant to provide emotional depth for her end up seeming flat or unrealistic to me. Diaz has been good in other things, but here I think the material’s not strong enough to let her succeed, or else maybe she’s not quite strong enough (unlike Winslet) to elevate it. Maybe both. There are still, for sure, some good moments for Diaz and Law, especially later in the film where we’re seeing a life that’s a lot less artificial and flashy. In the end, though, I found myself rolling my eyes or checking my watch too often when one or both of them was on screen.
I Know That Face: In this category, there’s a couple of people with fun crossovers into holiday movie territory. The aforementioned Eli Wallach, Amanda/Iris’s charming elderly next door neighbor Arthur, narrated The Gift of the Magi in 1958 — a TV movie you probably didn’t see, unless you were around in 1958, I’m guessing — and appeared as a character named Behrman in a segment called “The Last Leaf” in another TV movie, O. Henry’s Christmas, that, yeah, you probably didn’t see unless you were watching television in 1996 (I was, but I don’t remember this one: you can apparently watch a terrible transfer of the whole thing on YouTube right now). Arthur’s Hanukkah buddy, Ernie, is played by Bill Macy (no, not William H. Macy….an older actor who, I presume, is part of the reason there’s an “H.” in William H. Macy, given Screen Actors Guild rules about having distinctive working names) who also plays a character named Doo-Dah in Surviving Christmas, yet another semi-forgotten 2000s holiday flick, and one I’ve never seen. Shannyn Sossamon, who plays Miles’s crappy girlfriend Maggie, turned up in 2021’s High Holiday, which is apparently a movie about a family Christmas dinner in which someone slips weed into the salad dressing so that everyone (including her right wing politician father) will get blazed and say their true feelings out loud? Sounds ghastly…I guess maybe someday I’ll watch it and find out.
That Takes Me Back: I have to say, there’s a number of slices of classic mid-2000s life here. Iris’s job is writing wedding columns for a British newspaper, and while we get only glimpses of her older word-processing software in use, the fact that she’s working in old school journalism at all feels quaint these days. At one point Amanda’s awful ex shouts at her, “You sleep with your BlackBerry.” Can’t get more 2006 than that. Iris is carrying a BlackBerry around, too, sending emails on it from the plane (prior to takeoff, we assume). When Amanda searches for vacation homes to escape to, she types in a simple keyword search and gets actual functional Google results with no ads or promoted posts cluttering things up: talk about things we didn’t appreciate until they were gone. And one of the most charming and funny and ultimately sad scenes for Iris and Miles unfolds as they peruse a video store stocked with every kind of film on DVD — I miss those places all the time anyway, but especially when I’m trying to track down forgotten holiday films.
I Understood That Reference: I wish there was anything of this kind to dwell on here, but somehow in a film that’s at least partially obsessed with classic Hollywood films and movies with great music (thanks to the careers of Arthur and Miles respectively, and their effusive personalities), no holiday-themed media ever comes up in the film’s screenplay, even in passing. It’s a real missed opportunity.
Holiday Vibes (5/10): I don’t want to seem ungrateful: after all, Meyers opens the movie at an office holiday party, and the soundtrack is chock full of Christmas bops, including multiple people singing to us about a merry little Christmas and Motown singers walking in a winter wonderland. But the film’s not all that interested in Christmas other than as set dressing — there’s no family Christmas gathering on either side of the pond, only a couple of painful gift exchanges, and as the movie progresses, the sound’s less Motown and more Imogen Heap (which is not a complaint: I love Imogen Heap). None of these people seem to be living lives in which ordinary Christmas activities are really part of the routine — it would have made sense to have a “frantic shopping for Christmas gift” section, or a “my homesickness is assuaged by this particular Christmas memory or moment that feels familiar” but it’s not in the cards.
Actual Quality (8/10): It’s a solid Nancy Meyers movie with a great cast — there’s more than enough great set design and good cinematography, and some lovely people to watch fall in love on screen. Hard to be disappointed in that. It still drags at times, as noted, in the Amanda/Graham sections, and I found myself wondering how awesome it would be to just have a film about Iris — an English fish out of water in Southern California for Christmas, simultaneously finding herself loving and being loved by two sweet fellows, an elderly Hollywood widower who’s surely being reminded of the love of his life and a teddy bear of a film composer with an impish grin who’s on the rebound himself. That film, I think, had real 9 or 9.5 out of 10 potential, especially with Winslet, Wallach, and Black in the main roles. As it is, it’s a solid B- of a film, for me.
Party Mood-Setter? To me, no — it’s too sexual for Christmas with the kids but not sexy enough for a more flirtatious party of young adults. It’s playful enough and cinematic enough at times to get closer to qualifying, especially with those lush Nancy Meyers interiors, but fundamentally it’s a movie that needs your whole attention, and that wants to deliver most of its message through scenes that are at least a little poignant. Not great for inconsistent attention while you’re doing something else.
Plucked Heart Strings? This one is much closer, for me, but it’s still a no — the movie invests most of its big emotional arc in Cameron Diaz as Amanda, which again I think is not really working on either a screenplay or an acting level. If you do get misty-eyed at this film, I think it’ll be out of sympathy for Kate Winslet’s Iris, whom she makes a human being with genuine pain in her life that she needs to triumph over. I can see it — it just didn’t happen for me.
Recommended Frequency: This is definitely a “now and then, in the right mood” film, from my perspective. There’s not enough here to make it a perennial classic, especially because, ironically, the actual holiday content in a film called The Holiday is a bit thin. But it’s also more than watchable enough, especially (as I’ve made pretty plain) the to-me-superior subplots involving Iris, for me to imagine putting it on again in the future, now and then, when I’m in the mood to see particular moments or a particular acting performance again.
You can find The Holiday streaming on Amazon Prime, or for rent at the usual places (AppleTV, Google Play, Fandango at Home, etc.). You could pick up the Blu-ray (or DVD) at Amazon pretty inexpensively, it looks like. And of course I will always recommend you check at your local library: according to Worldcat, there are thousands of copies waiting out there for you! As will always be true here, I earn nothing from any links I’m providing: they’re just here as a courtesy. If you give the movie a go, I hope you’ll leave your thoughts in the comments!
Agree with so so much of this! I think the issues with Amanda and Graham have some to do with script and some to do with chemistry; Diaz and Law seem like two people who really liked each other but had no romantic chemistry in the film, no sparkle. The only part where they really worked for me was the spoiler part you omitted which worked for me; I felt they connected there and that was moving.
Arthur and Iris is the best part bar none.
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Meg, I’m delighted we overlap so well on this one — surely with the volume of movies ahead, I won’t always be so lucky, but I look forward to hearing your takes! Yeah, the part that worked for you, I did want it to work, but I felt like I was forcing an emotional connection rather than feeling it. I’m glad that was accessible for you — and I hope folks who like the movie will keep liking it! More motion pictures ahead for us to ponder. 🙂
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I only finally watched this one last year because I bought it cheap at a library sale. However, unlike you, I really enjoyed it and the DVD immediately went into my “keeper” Christmas” pile to have in regular rotation at the holidays. I hadn’t thought of how non-Christmasy it actually is, but I do agree with you there. It has the same issue as Christmas in Connecticut–despite the name, the basic plot (and even most of the details) could occur at any time of year.
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You’re not alone, Sly — several friends on Facebook boosted this as a top-tier holiday favorite for them, which is awesome to know even if it’s not grabbing me the same way. Your analogy to Christmas in Connecticut is a good one — I like that film but it also has never fully captured me. It’s high on my list for a potential slate next year, though, and I guess we’ll see if one more viewing makes a difference to me!
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