‘The Holiday’ Turns 14: See Cameron Diaz, Kate Winslet & More Then & Now

'The Holiday' is one of those perfect Christmas movies to cozy up and watch every year. The beloved film was released on this day in 2006. See 'The Holiday's core four then and now.

Cameron Diaz
Image Credit: The Everett Collection/AP

Every year around the holidays, there are just certain movies you love to watch over and over again. The Holiday is one of those movies. The rom-com has made our 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. Talk about the most adorable meet-cute premise. The Holiday featured a star-studded cast. Get updates on where the stars of The Holiday are today.

Cameron Diaz

Cameron Diaz
Cameron Diaz played Amanda Woods. (The Everett Collection/AP)

Cameron Diaz, 48, was already a major Hollywood actress when she starred as Amanda Woods in The Holiday, having been in the Shrek movies and Charlie’s Angels movies. Following the success of The Holiday, Cameron reprised the role of Fiona in Shrek the Third, which was released in 2007. That same year, she split from then-boyfriend Justin Timberlake.

Over the years, she starred in a number of hits like Knight and Day (with Vanilla Sky co-star Tom Cruise) and Bad Teacher. Her final film roles were the comedy Sex Tape and the latest film adaptation of Annie in 2014. Cameron announced she had retired from acting in 2018.

Since retiring, Cameron has welcomed a daughter, Raddix, who was born in 2019. She married Benji Madden in 2015. Cameron launched an organic wine brand in 2020 called Avaline.

Kate Winslet

Kate Winslet
Kate Winslet played Iris Simpkins. (The Everett Collection/AP)

Kate Winslet, 45, was one of Hollywood’s most in-demand actresses when she took on the role of Iris Simpkins in The Holiday. In the next few years after The Holiday, Kate won the Academy Award for Best Actress for her role in The Reader and reunited with Titanic co-star Leonardo DiCaprio for Revolutionary Road. She also joined the Divergent film series.

She earned another Academy Award nomination, this time for Best Supporting Actress, for playing Joanna Hoffman in Steve Jobs. Her most recent work is starring alongside Saoirse Ronan in the period romance Ammonite and voicing the titular horse in the Disney+ film Black Beauty. Kate will star in the HBO limited series Mare of Easttown and Avatar 2, the highly-anticipated Avatar sequel. Kate learned to free-dive for the part and was able to hold her breath underwater for 7 minutes.

The actress’ second marriage to Sam Mendes ended in 2010 after 7 years together. They divorced in 2011. Kate married Ned Rocknroll in 2012. Kate has three children.

Jude Law

Jude Law
Jude Law played Graham Simpkins. (The Everett Collection/AP)

Jude Law, 47, played Graham Simpkins in The Holiday. He went on to star as Dr. Watson in the Sherlock Holmes movies alongside Robert Downey Jr. He’s also known for playing young Albus Dumbledore in Fantastic Beasts: The Crimes of Grindewald. Jude has also starred in movies like Captain Marvel, Spy, Contagion, and more.

He’s also dabbled in television with shows like The Young Pope and The New Pope. The actor recently starred in the HBO miniseries The Third Day. He will be reprising his role as Albus Dumbledore in the next Fantastic Beasts movie and will play Captain Hook in the live-action Peter Pan.

The same year that The Holiday came out, Jude’s relationship with Sienna Miller ended. Jude’s welcomed two children with his former girlfriends Samantha Burke and Catherine Harding. He married Phillipa Coan in 2019. They welcomed their first child, Jude’s sixth, in Sept. 2020.

Jack Black

Jack Black
Jack Black starred as Miles Dumont. (The Everett Collection/AP)

Jack Black, 51, played Miles Dumont in The Holiday, playing Kate’s love interest. 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.

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