‘The Holiday’ Turns 16: See Cameron Diaz, Kate Winslet & More Then & Now

‘The Holiday’ is one of those perfect Christmas movies to cozy up to and watch every year. The 2006 film also featured a star-studded cast. Learn what they’re up to now.

There are certain films that come to mind when you need a comforting movie to cozy up to come holiday time, and The Holiday is one of those movies. The rom-com has made hearts melt every year since it was released on Dec. 8, 2006. The movie follows two women who swap homes in each other’s countries, where they each meet a local guy and fall in love. Aside from the adorable premise of the movie, The Holiday featured a star-studded cast: Cameron Diaz, whose character falls in love with the man played by Jude Law, and Kate Winslet, whose romantic interest is Jack Black.

Fans have been itching for a The Holiday sequel for years, and on Dec. 5, 2022, it was reported that a script had been greenlit. Sadly, the film’s director, Nancy Meyers, and Kate Winslet said the rumors are not true. “So many DM’s about this – sorry but it’s not true,” Nancy wrote on Instagram on Dec. 6. That same day, Kate said she had never even been informed of a reboot in an interview with PEOPLE. “I read something about that, but it’s the first I’ve heard of it. I promise you not an agent or a representative or anyone from the first one around has had any conversation with me about that,” she confirmed. “Hand on heart, that’s never come up.”

So, what are the stars of The Holiday up to since they’re not busy rebooting the classic Christmas film? Read on to lean about what the main cast of The Holiday below.

Cameron Diaz

Cameron Diaz, 50, was already a major Hollywood actress when she starred as Amanda Woods in The Holiday. She turned into what many would call an overnight success after her 1994 film The Mask debuted. Her star power was cemented with her leading roles in 1997’s My Best Friend’s Wedding, 1998’s There’s Something About Mary, and of course, the iconic Charlie’s Angels movies. She also voiced princess Fiona in the original Shrek films.

Between 2003 and 2007, while she was one of the biggest stars of the time, Cameron was also in a high-publicized relationships with Justin Timberlake. After that, she tried to keep her romances under the radar — especially with magician Criss Angel, who she dated briefly following her split from Justin.

Cameron had a huge year in 2014: Not only did she star in her last film before her retirement, the remake of Annie, she met the love of her life. She and Good Charlotte rocker Benji Madden had actually crossed paths once in 2004 at NSYNC’s Challenge For The Children Celebrity Basketball Game, but they didn’t officially meet until Cameron’s pal Nicole Richie and her husband, Benji’s brother Joel Madden, introduced the pair. “The first thing I said when I first met my [would be] husband was, ‘He’s hot,’” she told Andy Cohen on his radio show, per E! News. “How come I didn’t know this before? We had never been in the same circle.”

The pair tied the knot in 2015 and welcomed their daughter, Raddix, in 2019. “Happy New Year from the Maddens! We are so happy, blessed and grateful to begin this new decade by announcing the birth of our daughter, Raddix Madden,” the couple wrote in a joint Instagram post in Jan. 2020. The happy couple also noted that while they were “overjoyed to share this news”, they said they felt a “strong instinct to protect our little one’s privacy.” They concluded, “From our family to all of yours, we’re sending our love and best wishes for a Happy New Year and Happy New Decade.”

After officially announcing her retirement in 2018 and taking some time to grow her family, Cameron pleasantly surprised fans in 2022 when she signed on to star alongside Jamie Foxx in the Netflix film, Back in Action. “It’s a little bit of muscle memory, you know what I mean?” she said on a Sept. 2022 episode of The Tonight Show Starring Jimmy Fallon about her acting return. “I did that for so long, it’s kind of like the process, I kind of just fell back into it. But it feels a little bit different.”

Kate Winslet

Kate Winslet, 47, was one of Hollywood’s most in-demand actresses when she took on the role of Iris Simpkins in The Holiday. In the years after The Holiday, Kate won the Academy Award for Best Actress for her role in The Reader and reunited with her Titanic co-star Leonardo DiCaprio for Revolutionary Road. She earned another Academy Award nomination in 2015, this time for Best Supporting Actress for portraying Joanna Hoffman in Steve Jobs.

In 2022, she played Ronal in the long-awaited Avatar sequel, Avatar: The Way of Water, a movie that grabbed the record for the biggest box office opening in the post-pandemic world. More impressively, she broke Tom Cruise‘s record for the longest time someone has ever held their breath under water for a film by doing so for seven minutes and 15 seconds. “I have the video of me surfacing saying, ‘Am I dead, have I died?’ And then going, ‘What was [my time]?'” she told Total Film in Dec. 2022. “Straight away I wanted to know my time. And I couldn’t believe it… The next thing I say is, ‘We need to radio set. I wanted [director James Cameron] to know right away.”

On the more personal side of her life, Kate’s marriage to Sam Mendes ended in 2010 after seven years. The Ammonite actress married Ned Rocknroll in 2012. Kate has given birth to one child during each of her three marriages.

Jude Law

Jude Law, 49, played Graham Simpkins in The Holiday. He went on to star as Dr. Watson in the Sherlock Holmes movies alongside Robert Downey Jr and as young Albus Dumbledore in the Fantastic Beasts movies. He’s also dabbled in television with shows like The Young Pope, The New Pope, and The Third Day.

Her also has some exciting projects in the works. He is playing the villainous character of Captain Hook in the live-action Peter Pan & Wendy movie, which is set to debut in 2023, and he landed a role in the Star Wars franchise series, Skeleton Crew, which is also due out in 2023. “It’s a galaxy far, far away … I mean that,” he replied after he was asked by Variety about how his inner child would feel about him joining the franchise. “[Star Wars] was such an important part of growing up. The impact of that film and that world, the way it penetrated and exploded my imagination, that there are more than one or two times every day where I’m walking on the sets where it hits me like a child. I get awestruck by certain characters that are around me. … it’s a wonderful experience.”

Aside from expanding his career, Jude expanded his family over the years. The same year that The Holiday came out, Jude’s relationship with Sienna Miller ended. He then welcomed two children — daughter Sophia in 2009 with his former girlfriend Samantha Burke and daughter Ada in 2015 with his ex, Catherine Harding. He married Phillipa Coan in 2019, and they welcomed their first child together in Sept. 2020. The actor was already father to son Rafferty, 26, daughter Iris, 22, and son Rudy, 20, with his ex-wife, actress Sadie Frost.

Jack Black

Jack Black, 53, played Miles Dumont in The Holiday. The comedian went on to lead the Kung Fu Panda franchise from 2008 to 2016. He’s also starred in hit films like Goosebumps, Jumanji: Welcome to the Jungle, and Jumanji: The Next Level. He earned his second Golden Globe nomination for his performance in the 2011 film Bernie. Jack launched the YouTube channel, Jablinski Games, in 2018.

Jack married Tanya Haden in 2006. They have two children together.