Diaz assumed the role of Amanda Woods, a workaholic movie producer whose boyfriend reveals he's been cheating on her, right before Christmas no less. Desperate for a shakeup, she heads to the British countryside for a house swap with Iris (Winslet), where she meets her charming brother Graham and soon finds herself falling for him.
Prior to filming, Diaz was a well-recognised face in the industry, having taken out several awards including an MTV Movie Award for Best Performance in There's Something About Mary (1999) and an MTV Award for Best Dance Sequence in Charlie's Angels (2001).
To almost everyone's dismay, Diaz made the decision to quit acting in 2014 in order to make her life "more manageable," per Variety. However, the actress shocked the entire world on June 30 when she announced that she would be returning to the big screen in a Netflix action comedy. Starring alongside Jamie Foxx, the flick, titled Back In Action will be starting production later this year.
Cameron married Good Charlotte guitarist Benji Madden in 2015, and welcomed their daughter Raddix, in December 2019.
The following year, she released organic wine label Avaline, alongside entrepreneur Katherine Power. She mostly lives a quiet life and appears happy to be keeping out of the spotlight for now.
The Holiday simply wouldn't be what it is without the divine essence that is Jude Law (also known as Graham Simpkins, also known as Mr Napkin Head). In the film, he arrives at his sister's cottage incredibly drunk, only to be greeted by the vivacious Amanda (Diaz), who he quickly finds himself smitten over.
In 2016, Jude told People that he's still “approached on the street about that film. Who knew? I didn’t know [what it would become] at the time, I’m just really happy that it’s something that people still enjoy."
While Mr Napkin Head is arguably his most famous role to date (seriously, this character is timeless), Law is still enjoying a successful career in the arts.
The actor won several awards for his leading role in the Broadway production of Hamlet, including the Falstaff Award for Best Leading Actor. He assumed the iconic role of Albus Dumbledore in Fantastic Beasts: The Secrets of Dumbledore (2022), Dr. John Watson in Sherlock Holmes (2009) and the Pope in The Young Pope (2016). Most recently, Law has just wrapped production as Captain Hook in Peter Pan & Wendy and a third Sherlock Holmes movie.
Jude is now a proud father of six: Rafferty, Iris, and Rudy Law from his marriage to Sadie Frost; Sophia Law whom he shares with Samantha Burke; Ada Law from his relationship with Catherine Harding; and a one-year old with his wife Philippa Coan.
Taking on the role of Iris Simpkins, Winslet was an adorable, lovesick columnist who was totally and completely in love with the wrong man. After finding out he's engaged, she flees to LA for a house swap with Amanda (Diaz), and befriends her delightful, elderly neighbour, before slowly falling in love with Miles (Black).
At the time, Winslet revealed she was terrified of not being funny enough, having had limited experience in romantic comedies. In an interview, she said:
“I’ve never done a romantic comedy or something that is labelled as that before. I was so excited to do something new and also nervous you know? The worry of, ‘Can I be funny?',” adding that, "Jude [Law] and I would speak on the telephone a lot before we started shooting. ‘Oh my god, they’re going to fire us! They’re going to recast. What if we don’t make them laugh?’”
Interestingly, the film’s creator Nancy Meyers actually wrote the role of Iris with Kate Winslet in mind, explaining in an interview that when you think of “a 30-year-old-woman in England”, your mind immediately goes to Kate Winslet.
After making us laugh (lots) in The Holiday, Winslet has remained on our screens in a variety of roles. Of course, she was already a globally recognised name, having starred in The Titanic, with the actress later taking home countless awards, including an Academy Award for Best Actress in The Reader (2008), a BAFTA for Best Supporting Actress in Steve Jobs (2016) and a Golden Globe for Best Actress in Mare Of Easttown (2022).
As for her personal life, she married Edward Abel Smith in 2012 and welcomed a child, Bear Blaze in 2013. She also has two other children, Mia Honey Threapleton and Joe Mendes, from her previous marriages to Jim Threapleton and Sam Mendes.
Black, who was predominantly known for his comedy roles at the time, was wonderfully endearing in The Holiday as a composer named Miles. He discovers his awful girlfriend Maggie kissing another man, and soon finds himself seeking comfort in the arms of, you guessed it, Iris (Winslet).
Although we found his performance unforgettable, it seems the actor found it very forgettable. When Variety interviewed him on the Jumanji: Welcome To The Jungle red carpet about his favourite Christmas movie, he said, "I gotta say Elf, […] Jon Favreau and Will Ferrel just knock it out of the park." After being prompted about his own movie, he responded: "Do I have a Christmas movie? Which one is mine? […] Oh, The Holiday! Obviously The Holiday. Nancy Meyers: Genius."
We'll forgive him, this time.
In 2009, Black won an MTV Award for Favourite Animated Voice for his work in the Kung Fu Panda. He also went on to star in Gulliver's Travels (2010) The House with a Clock in its Walls (2018) and Jumanji: Welcome to the Jungle (2017).
He is also still performing in his comedy rock duo, Tenacious D as the lead singer and guitarist. The band now have four albums to their name.
In 2018, Back was given a star on Hollywood's Walk of Fame to solidify his A-list status. He is married to artist and musician Tanya Haden Black, with whom he shares two children, teenager sons Thomas & Samuel.
Jude Law's daughters in The Holiday were arguably the beating heart of the entire film. After Amanda discovers that Graham has two young daughters, she spends the most heartwarming evening with them drinking hot chocolate, laying in their fort and being introduced to Mr Napkin Head.
Englefield, who was just six-years-old at the time of filming, told Vulture in 2019 that bagging the role was a huge win for her family, who were struggling financially at the time.
She also revealed that the cast were incredibly welcoming, saying:
"They had all the time for us in the world. Jude used to pop his head round the door when we were doing our schooling and things like that. He used to sit and chat with my dad. We did act like a family a little bit, and I think that shows in our relationship onscreen. We were all so close and that wasn’t just for when the cameras were rolling. We were always just chatting, making jokes, and having a really good time."
Are you ready to feel old? Because little Miffy is now a mother, welcoming a daughter named Frankie back in 2020.
Job wise, she was last said to be working as a barista and is very into the punk rock scene, debuting a range of tattoos and proving that she really is all grown up.
She's also on TikTok where she shares 'day in the life' videos and sometimes, if we're lucky, reveals BTS tidbits about her time on The Holiday.
Taking on the role of Olivia, Graham's youngest daughter, Pritchard was beyond cute in her knitted sweater. We don't know too much about her character, except that she's a big fan of extra marshmallows in her hot chocolate, and of course, of Mr Napkin Head.
Pritchard is now in her early twenties and is no longer acting. IMBD lists The Holiday as her only role and she doesn't appear to have much of a social media presence.
Taking on the role of most-hated man in the movie (AKA Ethan, AKA the man who cheated on Diaz' character Amanda), we didn't see much of Burns, and gladly so. Still, his five minutes are burned into our memories forever, as a reminder that men really can be the worst.
Edward has starred in a number of projects since The Holiday, including Entourage (2006), 27 Dresses (2008), Friends With Kids (2011) and Public Morals (2015).
Nobody can forget his role as George in 27 Dresses, where he emotionally tortures Katherine Heigl before proposing to her sister. Seriously, why is this man so good at playing horrible men?
Burns is married to the supermodel Christy Turlington, with whom he shares two children, Grace and Finn.
The other horrible male character in The Holiday was brought to you by Rufus Sewell, who played the role of Jasper, Iris' emotional tormentor. Who can forget the iconic text Winslet's character sent him which read: “Jasper, We both know I need to fall out of love with you. Would be great if you would let me try," before the plane to LA took off.
Bizarrely, Ranker claimed that Sewell and Winslet dated briefly from 1995-1996 – which might have made filming a little strange, but they two are nothing if not professional.
Despite playing one of the worst men in the film, Sewell's other roles have seen him a little less hated.
He recently starred in M. Night Shyamalan's psychological thriller, Old (2021), and prior to that, starred in Hercules (2014), The Tourist (2010) and Judy (2019).
He has a son William, who he shares with Amy Gardner, and a daughter Lola, to Ami Koma.