Movies about movies usually draw back the veil on the filmmaking process, but in 2006, Nancy Meyers made a different kind of movie about movies. Although The Holiday is only tangentially relate d to the film industry itself (one character cuts movie trailers, another composes scores, one’s a retired giant of the Golden Age of Hollywood), it’s very much a film about romantic comedies—how they’re structured, what we want from them, and the affect they can have on us. It pulls off a tricky balancing act, one that’s even more impressive than it seems at first glance. It’s a genuine, unapologetically cheesy rom-com that’s also a bit of a meta one, too.


While The Holiday hasn’t quite reached Love Actually-levels of divisiveness, it does tend to engender strong feelings about which half of its bifurcated structure is better. On the one side is Kate Winslet as Iris Simpkins, a Surrey-based wedding columnist who’s spent the past three years unable to get over her cheating ex-boyfriend/current coworker Jasper (Rufus Sewell). On the other side is Cameron Diaz as Amanda Woods, an L.A. workaholic who struggles to feel much at all about dumping her own cheating boyfriend (Edward Burns). Both in desperate need of a shake-up, the two women meet on a home-exchange website and agree to swap houses for a two-week Christmas vacation. Iris gets a chance to unwind in the lap of luxury, while Amanda is forced to let go of her micro-managed routine.

It’s immediately clear that The Holiday’s protagonists are two very different types of people. Iris is a lovelorn sad sack who can’t find the courage to speak up for herself, while Amanda is a high-strung control freak who hasn’t cried since she was 15 years old. But what’s maybe less immediately apparent is that they’re in two very different kinds of romantic comedies. After Amanda impulsively hooks up with Iris’ dashing older brother, Graham (Jude Law), they fall into a two-hander in the vein of When Harry Met Sally, in which both of the romantic leads have their own arcs. Iris, however, experiences a story that’s closer to Bridget Jones’s Diary or 27 Dresses, in which romance is just one part of the protagonist’s self-actualization journey. It’s what Crazy Ex-Girlfriend showrunner Aline Brosh McKenna calls the “and-a-man” model of storytelling, where finding love is a bonus, not the central focus.

So while I’ve seen critiques that the Iris section of the film doesn’t devote enough time to her eventual love interest, Miles (Jack Black), that’s very much a feature, not a bug. Iris has spent far too much of her life obsessing over romantic love, so she gets an arc that’s about learning to value friendship as much as romance, cutting out toxic people, and starting a relationship from a healthy, non-obsessive place. Amanda, meanwhile, gets a love story all about learning to open up her heart despite the risk. Together the two halves of The Holiday celebrate the variety of stories that can be found within a genre that’s often accused of being one-note and repetitive.


While that might sound a bit didactic on the page, The Holiday deploys lightly meta elements to add a sense of playful self-awareness to its rom-com tribute. Amanda edits movie trailers for a living, and she has recurring nightmares in which her struggles are narrated with the kind of cheesy voice-over that has anchored many a real-life rom-com trailer. It’s a conceit that lets you know The Holiday is very much aware of what kind of movie it is. Iris, meanwhile, befriends living legend Arthur Abbott (then 90-year-old Eli Wallach), the screenwriter we’re told added the “kid” to Casablanca’s “Here’s looking at you, kid.” He talks her through the beats of a classic romantic comedy and gives her recommendations for old movies starring empowered women. As The Holiday sets about delivering its meet-cutes, Arthur is there to helpfully define that term for the audience.

The Holiday isn’t above the kind of self-aggrandizing that’s often a hallmark of movies about movies. When Arthur informs Iris that in screenwriting terms she’s a leading lady who’s behaving like the best friend, she tearfully responds, “I’ve been going to a therapist for three years, and she’s never explained anything to me that well.” It’s perhaps unsurprising that Meyers—herself a lifelong screenwriter—would so exalt the power of her chosen profession. Yet the scene also has a ring of truth for anyone who’s ever processed an element of their life through pop culture.

By 2006, Meyers had firmly established herself as the reigning queen of romantic comedies. After co-writing iconic ’80s and ’90s comedies like Private Benjamin, Baby Boom, and Father Of The Bride, Meyers struck out on her own as a writer-director with The Parent Trap, What Women Want, and Something’s Gotta Give. The latter solidified what we think of as a “Nancy Meyers romantic comedy,” which are usually filled with immaculate kitchens, cream-colored sweaters, and the whimsical problems of wealthy middle-aged creatives. The Holiday is a little outside her norm in that its leads are younger and seemingly less burdened by topics like divorce and parenthood—at least until it turns out Amanda is permanently scarred by her parents’ breakup and Graham is secretly a widowed single father.


Although Diaz was the rom-com veteran of the cast (she’d previously starred in There’s Something About Mary and My Best Friend’s Wedding, among others), she’s saddled with the weakest character and never quite figures out how to make her work, despite giving it her all. Winslet and Black fare better as two nice, gentle people who spend most of the movie making each other laugh. This was Winslet’s first and so far only foray into a big studio rom-com and she gets the tone of her performance just right. While Black had previously starred opposite Gwyneth Paltrow in the Farrelly brothers’ abysmal Shallow Hal, The Holiday capitalizes on the gentler type of leading man charisma he brought to School Of Rock a few years earlier. As with Billy Crystal in When Harry Met Sally or Adam Sandler in The Wedding Singer, Black’s casting is a great example of a rom-com recognizing the importance of a male lead with genuine comedic charm.

But the film’s best performance comes from Jude Law, who, like Winslet, was making his first try at romantic comedy. This was also the capper to Law’s wild run as an early aughts leading man (he appeared in six films in 2004, including the rom-dram Alfie) before reinventing himself as a character actor. If Amanda is the character saddled with the most tropes, Graham is the film’s most original one. He’s playful and gentle and great at listening, which are the qualities that make him a good dad, though we don’t learn that full context until late in the film. That makes him a compelling, emotionally vulnerable enigma, and helps elevate the Amanda side of the story.

While Meyers’ films may not be realistic, she does have a great eye for specificity—like the way Graham entertains his daughters with a character called Mr. Napkinhead (himself with a napkin over his face). Meyers is also great at writing memorably snappy, character-revealing dialogue. After Graham talks about his parents’ publishing careers, Amanda admits she’d initially downplayed the fact that she owns her own company, adding, “Now that I know you were raised by such a strong working mom, I can say it and maybe you won’t be intimidated.” A lot of Meyers’ best lines go to Wallach, a real-life screen legend who knows just how to play his endearingly old-school fictionalized one. In describing his wife, Arthur notes, “She had real gumption. She was the girl I always wrote.” That same sweetness is carried on in Miles, who introduces the theme music he wrote for Iris with, “I used only the good notes.”

Some of Meyers’ best writing comes in how realistically manipulative she makes Jasper, the ex who keeps worming his way into Iris’ life. “I wish you could just accept knowing how confused I am about all this,” he responds when she asks him to clarify whether he’s still engaged to someone else as he starts putting the moves on her. It’s a spine-tinglingly accurate depiction of gaslighting in action. So while the climactic scene in which Iris throws him out is zippy rom-com fun, it’s also rooted in an emotional truth about how toxic people operate and the strength it takes to cut them out. That’s a welcome message in a movie aimed at a broad audience. (Although The Holiday only grossed $63.2 million domestically, it made $205.1 million worldwide, and has only grown in stature since.)


It’s easy to write off Meyers’ films, which look and feel like a lot of the increasingly soulless romantic comedies of the 2000s. To be honest, I was a bit nervous about whether my long-time affection for The Holiday would hold up on a rewatch. The fairly broad first act didn’t do a ton to assuage my nerves, what with Iris’ blunt opening narration and Amanda’s goofy physical comedy about trudging through the snow in heels. Yet as the film goes on, it finds its groove in a really lovely way, with some light Christmas (and Hanukkah!) theming that doesn’t go overboard with festive cheer. The Holiday demonstrates there’s a real art to what Meyers does, the equivalent of whipping up a soufflé as light as it will go without letting it collapse.

The Holiday is very much a film of its era and its director, which will limit its appeal for those who prefer their romances grounded in something closer to the real world. But unlike Love Actually or its many copycat rom-coms, which attempt to deliver a definitive encapsulation of the genre by cramming in as many storylines as possible, The Holiday uses just two main throughlines to offer an even more effective tribute. It’s designed as a gift to rom-com fans, which makes it a perfect film for the holiday season.

Next time: We kick off 2020 by asking, “Is The Ugly Truth the worst rom-com ever made?”