Long before Hallmark and 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 with their festive fix for a 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.
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 their romantic lives (or lack thereof), the 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.
Updated on December 21st, 2021, by Lynn Gibbs: Cameron Diaz and Jude Law are the perfect pair in The Holiday, as are Kate Winslet and Jack Black. The story of a home exchange program during the holidays turned into a Christmas classic that fans rewatch every holiday season. Aside from the storylines, The Holiday’s cast made this movie the success that it is today. Every rewatch, however, brings more questions from viewers that have them wondering about what The Holiday was like behind-the-scenes. From Iris’ English cottage to the hilarity behind Jack Black, fans want to know everything about this movie since there doesn’t appear to be a sequel on the way.
Wallach plays Amanda Woods’ neighbor, Arthur. Arthur is an older man who needed help getting around, which is where Iris stepped in when she was staying in Amanda’s house. The two created a real bond and enjoyed each other’s company.
In real life, the cast and crew actually celebrated Wallach’s 90th birthday on set. It was amazing that Wallach was still acting in his 90’s! BuzzFeed noted that the crew got a big cake to celebrate the extraordinary occasion. Sadly, he passed away at the age of 99 in 2014.
Iris’ English cottage is small, charming, and cozy. Amanda’s home, on the other hand, is lavish, modern, and massive. Both homes are to be desired, which is why fans wanted to know if Amanda Woods’ home was actually real and where to find it.
Apparently, the outside of Amanda’s house is a real house that can be found in San Marino, California, according to Locations Hub. The inside of her home, however, was created at a studio. According to Cosmopolitan, the interior of Amanda’s house cost production $1 million — and it’s not even a real house!
As a famed director and writer from the Golden Age of Hollywood, Arthur gave Iris much-needed inspiration for her life… and movie collection. He gave her a long list of movies to watch that showcased leading ladies and powerful forces on the big screen.
BuzzFeed noted that before Miles interrupted Iris, she was about to watch a movie called Punch-Drunk Love. The film follows a lonely man who tries to find himself while falling in love with a British woman. It sounds awfully similar to The Holiday’s premise, which could have been a small hint of foreshadowing.
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, Dustin Hoffman—who was in The Graduate—is standing there.
Funny enough, this moment was never meant to be part of the movie at all. As a behind-the-scenes take on this Nancy Meyers film, the scene was by chance. 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 Meyers, he agreed to film a small cameo for the movie.
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, according to Coming Soon, 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.”
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, what some fans might not know about The Holiday is that when Iris runs around Amanda’s home and takes in the sights, her state quickly turns into euphoria — including an adorable moment of dancing that was entirely improvised by Winslet herself, noted Hollywood.
According to Cosmopolitan, there are rumors two of The Holiday‘s stars had a romantic history long before the movie was released.
Reports suggest that Kate Winslet and Rufus Sewell—otherwise known as the actors behind The Holiday‘s problematic and unrequited romance, Iris and Jasper—were once romantically involved for a brief period in the 1990s. If this is true, it certainly provides the relationship between their characters with a whole new level of tension.
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. The cozy cottage was home to some of The Holiday‘s sweetest moments. Surprisingly, Hooked On Houses noted that 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.
Since Amanda makes her career producing flashy trailers for movies, it’s fun that the film takes the time to show a few glimpses of her work. One of these such trailers features a few prominent faces — Lindsay Lohan and James Franco. 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. As Meyers said according to Coming Soon, “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.”
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 one of his best works as Dewey Finn 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.”
Miles is 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. According to E! Online, Meyers said, “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.”
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. Jude Law was not known for romantic roles at the time. Even though Law had spent his career 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.
Despite wanting him for the role, The Things noted that 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.
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,” Indie London noted her saying. However, apparently, his level of commitment didn’t preclude the potential for improvisation.
Miles is a likable 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.
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. Everyone involved in the production was apparently all too eager to learn about the days of Old Hollywood from Wallach. Apparently, Wallach was truly all too eager to tell the stories.
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.”
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.
In an interview with Variety, when Meyers was courting Black for the role, she 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. Funny enough, years later Black was asked about his Christmas movie and he forgot he even had one!
Much of what makes Iris’ sleepy little cottage home appear as idyllic as it does is the snowy picturesque landscape that surrounds it. If fans could swap places with a character, it would be Iris simply because of that cottage. When the movie was in production on location in England, Meyers recalled in an interview that 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 produce fake snow. Ironically, it snowed a couple of times during filming, which was the perfect gift.
There’s a long-known stereotype about the acting world that actors never 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.
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, in an interview, 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.
Iris’ friendship with Amanda’s neighbor, the adorable Arthur, is one of the movie’s strongest storylines. 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 comedic 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.”
When The Holiday was first released in 2006, sequels weren’t necessarily par for the course for most movies. 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, Marie Claire reported that 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. Some sequels go nowhere, and no one wants that for The Holiday.
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, according to an interview.
Cameron Diaz’s character is athletic and 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.
Regardless of whether fans find the romance between Miles and Iris to be a believable part of The Holiday‘s plot, a lot of care and consideration went into the creation of it. Nancy Meyers was 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 according to Bustle, admitted in a dual interview with Cameron Diaz for Moviefone that “it was not difficult to fall in love with Jack Black. At all.”
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.
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.
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.
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. Regardless if The Holiday is seen as a Christmas movie or not, there are theories for every possibility in the film.