20 Wild Details Behind The Making Of The Holiday

Long before Hallmark and Lifetime and, now, Netflix had cornered the market on the art of the Christmas romantic comedy, feel good big screen films like 2006’s The Holiday went a long way toward providing avid viewers everywhere with their festive fix for holiday romance. Starring a cast of big names, including Kate Winslet, Cameron Diaz, Jude Law, Jack Black, and old Hollywood icon Eli Wallach, The Holiday has become one of the time honored classics, even if the debate about whether the movie is actually any good still rages on twelve year after its release.

The Holiday follows two total strangers, Amanda Woods (Diaz) and Iris Simpkins (Winslet). While one is based in Los Angeles, the other resides in the English countryside. Dissatisfied with their current careers and the affairs (or lack thereof) of their romantic lives, the two women take part in a home exchange with one another for the holiday season — only to, of course, find love on the other side of the pond where they least expected anything of the sort. It’s a cutesy movie from start to finish that never takes itself too seriously — and that’s entirely what makes it work.

With so many storied Hollywood names in the cast, and with the movie being helmed by likewise big name Nancy Meyers, there just so happens to be an endless trove of amusing stories of all that went on behind the scenes.

Here are the 20 Wild Details Behind The Making Of The Holiday.

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Katharine Ross and Dustin Hoffman in The Graduate

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20 Dustin Hoffman was never meant to have a cameo

Katharine Ross and Dustin Hoffman in The Graduate

It’s a moment in the movie that’s always a good source for a quick chuckle, even if it stands out like a sore thumb. When Miles and Iris are in a video store and entertaining themselves with the soundtracks of classic films, Miles picks up a copy of The Graduate and begins to sing Simon and Garfunkel’s “Mrs. Robinson”. As Iris laughs at his antics, across the store, who should appear and hear them? Why, none other than the star of The Graduate himself, Dustin Hoffman.

This moment, in fact, was never meant to be part of the movie at all. According to the commentary track on the film’s DVD, Hoffman was merely in the area when this scene was being filmed and, since he is close with writer and director Nancy Meyers, he agreed to film a small cameo for the movie.

19 Iris and Amanda were written with Winslet and Diaz in mind

Sometimes, it can really feel like a part was meant to meet a specific actor or actress’ wheelhouse of talents. Iris is the more emotionally driven of the duo of female leads, with flourishing speeches and plenty of effusive tears. Amanda is more withdrawn, more self-deprecating, and more humorous overall. Kate Winslet is perfectly cast as Iris, and no one would have been better for the role of Amanda than Cameron Diaz.

As it turns out, these two were exactly who Nancy Meyers had in mind when she was crafting the script: “I wanted Kate and Cameron during the writing process. You know, I think a screenwriter would lie to you if they said, ‘I don’t think about anybody when I am writing.’ I can’t imagine it.”

18 Kate Winslet improvised Iris’ dancing

Kate Winslet as The Evil Queen Snow White

Amanda gets most of the movie’s comedic moments when it comes to female-driven comedy. Much of this is likely due to Cameron Diaz’s proven strength as a comical actress, especially since she was the one who Nancy Meyers had in mind while creating the character. However, Iris occasionally gets in on some of the hilarious fun, too — though perhaps without Meyers even having intended this to be so.

When Iris first arrives in Los Angeles, she’s entirely swamped by just how different things are versus life in picturesque Surrey, England. However, as she runs around Amanda’s home and takes in the sights and sounds, her state quickly turns into euphoria — nncluding an adorable moment of dancing that was entirely improvised by Winslet herself.

17 Winslet and Rufus Sewell have some awkward real life history

Kate Winslet and Rufus Sewell in The Holiday

These days, it seems like it’s becoming increasingly common for costars to pair up romantically behind the scenes — or, at least, it really feels that way, given the prevalence of tabloids and social media coverage. Yet actors have dated actors ever since the art form of film began. According to rumors, two of The Holiday‘s stars had a romantic history long before the movie was released.

Reports cited by Cosmopolitan and The Telegraph suggest that Kate Winslet and Rufus Sewell — otherwise known as the actors behind the movie’s unrequited romance, Iris and Jasper — were once romantically involved for a brief period in the 1990s. While we’ll never know for sure, it certainly provides the relationship between their characters with a whole new level of tension.

16 Iris’ cottage was built by production in two weeks

Iris's cottage in The Holiday

One of the big takeaways from watching The Holiday for viewers is often the overwhelming desire to whisk themselves away to stay in a little picturesque England village, in a place like Rosehill Cottage, which is the total polar opposite of basically anywhere in this day and age of internet and commercialism driven culture. So this next fact may be pretty hard for fans everywhere to hear: Iris’ dream home never existed to begin with.

All scenes in the interior of Rosehill Cottage were filmed on a set. The beautiful exterior of the cottage was built by the production crew in less than two weeks, the majority of time being spent on the elaborate greenery and plant life that can be seen in Iris’s garden and neighboring areas.

15 Lindsay Lohan filmed a cameo as a favor to Nancy Meyers

Since Amanda makes her career producing flashy trailers for action and romance movies, it’s fun that the film takes the time to show us a few glimpses of her work. One of these such trailers features a few prominent faces — Lindsay Lohan and James Franco. It’s an odd moment in the movie, even after all these years, to see such prominent Hollywood names in such a relatively insignificant aspect of the film. Yet as it turns out, Lohan’s involvement stemmed from a highly personal reason.

Nancy Meyers directed The Parent Trap remake in the 1990s, which more or less launched Lohan’s career: “I know Lindsay because I directed The Parent Trap and I told her she owes me everything so I made her do it. I called her and said, ‘You have to do this for me,’ but she was sweet about it, she was totally there.”

14 Jack Black was chosen because of his performance in School of Rock

School of Rock with Jack Black

It’s a sticking point for a lot of people with this movie: in what Hollywood typical world would a Kate Winslet fall in love with a Jack Black? Apparently, that was exactly the point Nancy Meyers intended to make with his casting. After seeing him in School of Rock, and particularly how hilarious and skilled he was when interacting with children, Meyers knew that he was exactly the kind of actor she needed for Miles.

As Meyers explained, “I’m aware he’s not Clark Gable, he’s not tall dark and handsome, but he’s adorable, he’s lovable. It’s my way of saying this is the right kind of guy, this is what most guys look like if they’re lucky, he’s so adorable, and why not? Everybody has a heart and deserves to fall in love and he should get a great girl.”

13 One of Iris and Miles’ signature moments had real life inspiration

Jack Black and Kate Winslet in The Holiday

The character of Miles is one who is perhaps best defined by the awkward humor he displays at all times. One of the moments that best displays his tendency to make a joke, even at the most awkward of moments, comes when he inadvertently bumps into Iris in a particularly intimate way, noting that he’s sorry for the “graze.”

As it turns out, this wasn’t in the script to begin with, and was instead something inspired by an interaction between Black and Meyer. “One day on the set he bumped into me and said, ‘Oh, sorry about the [chest] graze,’ and I just laughed so hard because men bump into women all the time like that and act like they didn’t do it, but he immediately said sorry about the [chest] graze so I wrote it into the next scene he did,” she said.

12 Meyers didn’t think Jude Law would fit the role

The characters of The Holiday all work because, despite the movie being a clichéd romantic comedy in many ways, none of the characters are stereotypical types. Graham is yet another clear example of this trend. Even though Jude Law had spent his career until that point in dramatic, alluring roles, Graham is a multifaceted character: he’s brooding romantic lead material, but he’s also a single father with a nerdy side, a farm to tend to, and many more emotions than any stereotypical male lead would normally show.

Despite wanting him for the role, Meyers had her doubts about Law’s ability to fit the part. “I wasn’t immediately sure that he was going to fit into the genre and do this kind of work. So I met with him and we went through the script together and he just got it. You know, he just hasn’t had a chance to do it before,” she said.

11 Black improvised many of Miles’s funniest moments

It may come as a surprise, given how much larger than life his characters usually are, but according to Nancy Meyers, Jack Black is tremendously down to earth and entirely committed to the roles he is chosen to play. “People have been asking if I had to reign him in but he’s not like that. He’s not bigger than life. He knows his lines, and he’s doing a character in our movie that doesn’t do outrageous things,” she recalled. However, apparently, his level of commitment didn’t preclude the potential for improvisation.

Miles is a character defined by doing silly, outlandish things, on admittedly varying scales. Much of that humor was originally in the script, to a degree, but it was Black’s interpretation of certain directions and discussions that allowed him to improvise alternate takes in a much funnier way.

10 Eli Wallach’s old Hollywood stories were apparently too entertaining

Eli Wallach in The Holiday

It’s not every day that a cutesy little romantic comedy movie like The Holiday is lucky enough to land a storied Hollywood legend like the late, great Eli Wallach. As you can imagine, everyone involved in the production was apparently all too eager to learn about the days of Old Hollywood from Wallach — and, apparently, Wallach was truly all too eager to tell the stories.

As Nancy Meyers recalled, Wallach was “so full of anecdotes that sometimes we had to say: ‘Eli, just let us get this take!’ But the problem is that everyone was so interested in him and what he had to say. There are so many stills on this movie of Eli sitting in a chair and all of us around him, listening.”

9 Black agreed to take the role after learning it was opposite Winslet

Kate Winslet and Jack Black in The Holiday

Nancy Meyers may have felt that Jack Black was the only fitting option for the role of Miles from fairly early on in the production of the movie, but as fate would have it, Black was originally totally baffled by the idea of performing in a romantic comedy — and not at all without reason.

When she was courting Black for the role, Meyers had Black over to her home for dinner. “When I asked him if he’d ever be in a movie like this, he replied: ‘Nancy, have you seen my work?’ But I assured him that I had and told him that I thought he was fabulous,” she said. However, it wasn’t until Meyers told Black he’d be starring opposite Winslet that he was willing to be open to the idea.

8 Much of the snow in the movie is real, even though production hired a snow company

Cameron Diaz in The Holiday

Much of what makes Iris’ sleepy little cottage home appear as idyllic as it does is the beautiful, serene snowy picturesque landscape that surrounds it. When the movie was in production on location in England, Meyers recalled, they were informed by the crew that “it never actually snows here anymore.” She was totally incredulous at that, claiming, “‘Really? But I saw snow in Bridget Jones!’ But they told me that it was just the movies.”

As a result of the clear need to do some movie magic behind the scenes, the movie’s production crew “hired a company to make snow and then, during the first week of shooting, it snowed maybe three times.” So yes, much of the beautiful snow that fills the movie is indeed the real deal.

7 Jude Law preferred Graham’s role of father to his romance

Graham's daughters in The Holiday

It’s a long-known stereotype about the acting world: actors never, ever want to work with children, because they’ll either be too difficult or entirely upstage their respective performances. However, in the case of The Holiday and star Jude Law in particular, it sounds like none of these stereotypes held true. While it would be easy to expect Law to reflect on the movie and claim that the romance was the highlight of it all for him, he instead claimed that Graham’s relationship with his daughters, Olivia and Sophie, was the high point.

Law commented on his own identity as a father in explaining his preference for those scenes, but there’s no way of ignoring just how adorable, heartwarming, and outright funny the moments between the single father and his two daughters are within the movie, making for some of the movie’s best moments overall.

6 The movie gets Cary Grant’s biography wrong

Cary Grant in Bringing Up Baby

Iris’ friendship with Amanda’s neighbor, the adorable elderly Arthur, is one of the movie’s strongest storylines without a doubt. The two banter with one another to quite amusing effect, even touching on some incredibly poignant matters along the way. However, it’s in an early moment when they discuss Iris’s place of origin — Surrey, England — that the movie runs into a factual error that many viewers from the U.K. took issue with.

Arthur tells Iris that the legendary actor Cary Grant was from Surrey, a fact with which Iris agrees. However, Grant wasn’t from Surrey at all, but rather, from Bristol. In a scathing review for The Guardian, long time movie critic Peter Bradshaw notes, “Unforgivably, Meyers’s script has someone saying that Cary Grant was from Surrey. My suspicion is that Meyers knows perfectly well Grant was from unpicturesque Bristol.”

5 Discussions about a sequel are ongoing

Cameron Diaz and Kate Winslet in The Holiday

These days, it’s getting to the point where it’s more surprising when a movie doesn’t get a sequel ordered than when a film does. Admittedly, back when The Holiday was first released in 2006, sequels weren’t necessarily par for the course for most movie. Also, even to this day, most romantic comedies don’t get to come back for a second installment, even if they’re enormously successful.

Yet even all of these years later, discussions about why The Holiday 2 hasn’t happened yet continue. Some of the stars of the movie have expressed interest in it, but nothing conclusive has ever been stated about when or how any sequel would happen, or what kind of storyline would even make sense, since much of the original film’s home swapping charm would clearly not be applicable here.

4 Cameron Diaz considers the movie her most physically tasking

Cameron Diaz Amanda in The Holiday

You would never describe The Holiday as an action movie. Okay, fine, there’s a trailer for an incredibly corny action movie embedded within the film that Amanda and her colleagues have put together. However, nothing about this slice of life romantic comedy would ever be described as action packed or high paced. Yet, all the same, Cameron Diaz has come to consider this movie as her most physically driven performance.

We can’t exactly blame her there. Amanda does have a lot of action heavy moments in the movie, whether drunkenly lapping the cottage as she screams along to “Mr. Brightside”, or running and trekking across the English countryside in high heeled boots when she first arrives and when she decides to stay at the end of the movie.

3 Winslet found it all too easy to fall in love with Black

Kate Winslet and Jack Black in The Holiday

Regardless of whether you find the romance between Miles and Iris to be exactly the most believable part of The Holiday‘s plot, a lot of care and consideration went into the creation of it. As we’ve already shown, Nancy Meyers may have been entirely committed to the casting of the roles from the start, even if co-star Jack Black had his own doubts about it.

However, someone who was entirely committed to the role and the relationship from the very beginning, too, was leading lady Kate Winslet herself, who admitted in a dual interview with Cameron Diaz for Moviefone that “it was not difficult to fall in love with Jack Black. At all.”

2 Most of Iris and Miles’ adventure in the video rental store is improvised

Jack Black and Kate Winslet in The Holiday

One of the most winning moments in the movie that feels like a real interaction between friends hovering along the boundary between friendship and something more comes when Miles takes Iris to a local video store and regales her with trivia regarding famous movie scores. Miles is entirely in his element here, and inviting Iris to join his world on yet another occasion – one that is more public, and more endearing and embarrassing all at the same time.

According to Meyers, this scene was scripted, but Black decided to improvise Miles’s singing method — using “doo doo”s instead of just humming as the script suggested, and introducing the awkward, yet hilarious lyrics of “are you embarrassed by this game I’ve started to play?” to the tune of the Gone with the Wind score.

1 The movie has attracted a series of incredibly dark fan theories

Kate Winslet crying in The Holiday

The internet is good for a lot of things, but one of the things that it truly excels at is making bizarre theories and poking holes in the idyllic haze of any beloved work of art. Over a decade removed from the film’s release, The Holiday has now begun to attract this sort of attention, including some truly dark and twisted fan theories that are not at all what was clearly intended.

In one fan theory shared by Entertainment Weekly in 2017, Iris and Amanda may not exactly have been alive for any part of the movie’s events. In another theory shared by Buzzfeed in 2017, there’s absolutely no possible way that any of these charac­­ters would ever have stayed together long term, which maybe makes the need for a The Holiday 2 entirely moot.

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What’s your favorite secret behind the making of The Holiday? Let us know in the comments!

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