A smart, wry romantic comedy for a bit more demanding viewers

Rating: 8/10 (17 February 2016)

Screenwriter/director Nancy Meyers continues to defy all romantic comedy conventions by doing a few things that are often missed by screenwriters of the genre. Instead of focusing on incredulous romances and meet-cutes, Meyers is quick to focus on the characters involved in these on-screen relationships, developing them by closely following their mannerisms before they become involved in the film's core romances. Secondly, she places emphasis on the dialog of the characters while they are in these relationships, rather than their actions, and even if circumstantial incredulity comes into play, you almost miss it because Meyers crafts such likable on-screen presences that it isn't so blatantly obvious that they are saying and doing things that are a bit too playful with narrative conveniences. Finally, the emphasis on conversation and character relationships helps Meyers naturally include humor and wittiness to a screenplay that would otherwise try too hard to be funny or relevant.
The end result is The Holiday, a very natural romantic comedy, with a quartet of strong performers and a story that takes its time to build over the course of two hours. Interestingly enough, most romantic comedies exhaust themselves past the one-hundred minute mark, but The Holiday defies convention by taking a liberal amount of time to illustrate two brewing romances on opposite sides of the world that all began because of adventurous feelings by two introverts.
The film opens by introducing two characters, Iris Simpkins (Kate Winslet), a column editor for a newspaper in London and Amanda Woods (Cameron Diaz), a movie trailer producer in Los Angeles. Iris has been in love with her coworker Jasper Bloom (Rufus Sewell) for over three years, despite him cheating on her when they were dating and that her love has gone unrequited. Iris winds up becoming more upset when she learns Jasper is engaged and she, well into her thirties, is still single. Amanda, however, has been a workaholic since the startup of her company, and the result has taken a toll on her live-in boyfriend (Edward Burns), who packs up and moves out after he reveals she has been cheating on her.
Both women are in need of a vacation, and upon discovering one another on a chat-room, they agree to a "house swap," where Iris will go live in Amanda's spacious, Los Angeles mansion and Amanda will live in Iris' small London cottage over the course of the holiday season. During her stay in Los Angeles, Iris meets an elderly man named Arthur Abbott (Eli Wallach), who was once a screenwriter during the Golden Age of Hollywood, in addition to Miles (Jack Black), a charming employee of Amanda's who has an obsession with films scores. Meanwhile in London, after initially slugging away at wine and holiday snacks, a drunk Amanda winds up meeting Iris' brother Graham (Jude Law) when he, also drunk, knocks on her door one night expecting Iris. The two commit to having a one-night stand, but when they realize their dynamic and chemistry is something neither of them can deny, the morning after becomes that much more complicated, especially when Graham allows Amanda to meet his kids.
The Holiday ostensibly sets itself up for immediate failure by focusing on two separate romances. That narrative structure is a constant problem with romance films because they struggle in trying to humanize and develop both relationships under a reasonable amount of time. For Meyers, time never seems to be a factor; she starts liberally, by revealing more about the characters through their mannerisms and their choices rather than by with whom they interact before inviting the love-interest into the picture. By including characters like Amanda's ex-boyfriend and Wallach's ex-screenwriter character, Meyers also shows that she has more on her mind than simply cranking out a dime-a-dozen love story. She wants to populate a film with characters that simultaneously mean something and fill a film with a great deal of entertainment value.
The result is a film that's breezily paced, but never fluffed, remarkably charming, but never saccharine, and humbly emotional, and never manipulative. This is largely thanks to Meyers' screen writing, but also thanks to the talented cast of performers, specifically Winslet and Black who are trying to break out of their own character archetypes throughout the entire film. Consider Winslet's character, who could easily be a faceless, mopey spinster. Instead, Winslet is a deeply sympathetic character because she's not dysfunctional nor is she a comical trainwreck. Consider the scene where Iris is beside herself, talking with Miles about the perils and the unrelenting sadness of unrequited love and it how strips not just a piece, but several pieces, from your ability to love, trust, and sympathize with people. It's a truly sad monologue that Meyers wisely doesn't choose to milk for tears, but rather, pure, unadulterated honesty.
Meanwhile, Black gives a performance that is perhaps his most delightful mixed of controlled chaos yet. While he is more restrained and casual here, his zealous, roly-poly tendencies sneak in on various occasions, particularly the video store scene where he brilliant recites harmonies and melodies of film scores. Cameron Diaz and Jude Law serve as the more predictable couple, though that's not a bad thing, for they are the narrative anchor that keeps the film from taking off into another world. You're bound to have a preferred couple watching The Holiday, and for me, the insights and the consistent charm of both Winslet and Black's characters was an instant winner for me.
With all that in mind, The Holiday works as a very lovable piece of entertainment, and furthers Nancy Meyers' status as one of the smartest female directors working in the business today. Her careful craft when it comes to assembling a romantic comedy is shown with every character in the film, and rather than cluttering Holiday with useless caricatures or sticking to a basic love quartet, she surprises on multiple levels, effectively giving most audience members more than they expected.