Nancy Meyers’ romcoms get stranger as they proceed, but The Holiday still stands as a pinnacle of weirdness – the last breath, perhaps, of the 90s romcom impulse that continued into the early 00s. The premise is brilliantly simple – a house-swap – allowing Meyers to move between sunny L.A. and cosy England as she follows two couples through the trials and tribulations of a ten-day relationship. Deciding that she needs time away from work, Amanda Woods, played by Cameron Diaz, agrees to swap her Los Angeles mansion for a small house in Surrey, owned by Iris Simpkins, played by Kate Winslet. As soon as she arrives, Amanda falls for Iris’ brother Graham, played by Jude Law, while Iris soon develops feelings for Amanda’s colleague Miles Dumont, played by Jack Black. Take an aging Hollywood screenwriter, Arthur Abbott, played by Eli Wallach, and you’d assume that this romcom would almost write itself.  

Instead, The Holiday over-writes itself, since Meyers is almost pathologically anxious about the relation between film and literature that fuelled so much 90s romantic comedy. On the one hand, Iris comes from a wealthy publishing family, studied literature at university and writes about marriage for The Daily Telegraph. We first meet in her in the thralls of an unrequited love for her chief editor, Jasper Bloom, played by Rufus Sewell, and this too is mediated through literature – she gives him a first edition just before he announces his engagement to another colleague, and she continues to edit his novel after she arrives in Los Angeles. Graham, her brother, has gone into the family publishing firm, which makes him doubly attractive to Amanda, who runs her own movie trailer company, but yearns for more meaningfully literary experience as well. In fact, when it all boilds down to it, her main motivation for travelling is that she “wants to read a book – not a magazine, an actual book.”

From the earliest scenes, then, Meyers seems anxious to find a common denominator between literary and cinematic romance – and she finds it in the writerliness of classical Hollywood, personified here by Iris’ neighbour Abbott, “the last of the great Hollywood writers.” Most of Iris’ romance with Miles is mediated through her friendship (or platonic romance) with Arthur, which culminates with her convincing him to accept a lifetime achievement award at a ceremony convened by the Academy of Motion Pictures. Whereas Iris travels to Los Angeles to recover classical Hollywood, Amanda leaves LA to recover it, but the product for both is the same – a romance with classical Hollywood that frequently makes the male leads seem like an afterthought, a mere projection of Iris and Amanda’s fantasy life.

Meyers taps into a rich vein of literary affectation in 90s romcoms here, from the bookstore where Hugh Grant works in Notting Hill, to the bookstore that Meg Ryan wants to save in You’ve Got Mail. These films seemed concerned by the fact the the longevity of literary romance depends on its formulaic qualities – the fact that it can be repeated with only small variations ad infinitum. The very appeal of the 90s romcom thus seemed to signal its decline, or at least its devolution into a series of utterly predictable cues. While classic 90s romcoms railed against this process, Meyers appears to have accepted that convention is inevitable, continually intercutting the key events with faux-trailers that present them in the most generic light. During the 90s, discussing conventions within films was often seen as a novel way to stave off conventionality, so while those discussions continue here, they feel more like a part of romcom convention in and of themselves, rather than any serious genre disruption.

Rather than thwarting convention, then, Meyers totally embraces it. In fact, I can’t think of a more deterministic mainstream romcom, since both women here fall in love with the first man they meet, explicitly discussing every genre cue until they inevitably end up coupled. That’s not to say that The Holiday is unambitious, though, since Meyers instead tries to restore the scale, majesty and magic that once accompanied convention, opting for a sweeping romantic aesthetic in which “anything can happen.” The result is much closer to a supernatural romance than a regular romcom (the manic energy doesn’t quite add up to comedy) as Amanda and Iris both find themselves surrounded by a mystical ether once they leave their comfort zones. In Los Angeles, Iris is regularly visited by the Santa Ana Winds, which start blowing at her first meeting with Miles (who explains them to her) and from thereon whip and swirl around her house, harbingers of romantic possibility. Conversely, all the spaces in England are crowded or cosy, making the vast expanse of snowy space outside seem even more mysterious, even more suffused with the prospect of romantic communion.  

In that sense, The Holiday picks up where Sleepless in Seattle and You’ve Got Mail left off. Whereas both those films inchoately grasped a future of online dating, The Holiday was released right when online dating was transforming from a fringe option to a mainstream option, without having descended into the franker and more venal dating apps of the current market. Since Amanda and Iris barely leave their respective houses, this often plays as a film about hook-ups disguised as a film about romance, blending hook-up and romance cues in quite bizarre ways. Meyers’ next film, It’s Complicated, would take its name from an early Facebook relationship option, and in many ways The Holiday feels modelled on the equivalent category when it comes to online dating apps – the “interested” option, which signals interest in a hook-up but also openness to any romance that might extend beyond it. The Holiday takes place in this novel zone (at the time) between online hook-up and romance, allowing Amanda and Graham to sleep together on their very first meeting without disrupting the romantic ether that could only before before physical consummation in Sleepless and Mail.

Unfortunately, there’s not a lot for the characters to do here, so enmeshed is the film in their fantasy lives. We open with two histrionic monologues from Amanda and Iris, which pave the way for a film that subsists entirely on monologues – in the form of voiceovers, letters, speeches and scenes where they introduce themselves, disclose their secrets, or give advice. Most of the film is pitched at the early introduction moments during a blind date, as the script collapses under an avalanche of overthinking and overtalking – a total navel-gazing exhaustion of anything that might remain for the 90s romcom to say. Beyond a certain point, it’s all blather, devoid of plot points, set pieces or pizzazz, as Meyers actually doubles down on convention so the film can free up all its energy for the scale and atmosphere of this transatlantic romance. You know it’s a problem when a romcom needs cheesy kids and old people to facilitate the romance, but that’s just what happens here, as Graham crystallises Amanda’s love by revealing that he’s a #GirlDad, and Miles wins Iris’ love by fanboying Arthur.

This quickly shifts The Holiday in a suffocatingly saccharine direction, which is pretty grating on its own terms, but also totally out of kilter with the classical Hollywood comedy that Meyers invokes at every possible turn. You wonder whether The Holiday cites Hollywood so often because it can’t summon up any wit of its own, since this screenplay doesn’t resemble 1930s and 1940s comedy in the slightest. Instead, it’s classical Hollywood cloaked in a haze of sententious Boomer nostalgia, taking the edge off all the comic spikiness and edginess that Preston Sturges – Meyers’ main point of reference – used to poke fun at the very studio system that The Holiday venerates. For all the pretentious finger-wagging about the Hollywood past, and for all its insufferable name-dropping, the flaccidity of The Holiday would never make it past a Meyer or Warner, and can barely maintain its momentum in the present.

It’s also a bit rich and corny to present the gatekeepers of old Hollywood as paragons of gentlemanliness – although Iris does confide that she’s “looking for corny” just before Arthur goes up to collect his award, in a sequence that reduces classical cinema to the most string-drenched sentiment of an Oscars ceremony. By this late stage, The Holiday is almost unfinishable, just because the film itself has no sense of how to finish, like an Oscar recipient who has well and truly overstayed their welcome. Even Amanda’s heroic run back to the cottage to declare her love for Graham – one of Jude Law’s most simpering roles – seems interminable; one gate after another, one field after another, one pause after another. In the end, Meyers simply seems to give up, cutting abruptly to the foursome back in England, in the Simpkins mansion, surrounded by the novels and literary affectation that ultimately does most of the heavy lifting in this most paranoid, pathological and plain weird of 00s romcoms.