The Holiday Cast: Where Are They Now?

We take a closer look at the star-studded cast of the festive favourite.
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Since its theatrical release in December 2006, The Holiday has become a modern Christmas-time classic. 

Directed by Nancy Meyers, the romantic comedy follows the two women, played by Kate Winslet and Cameron Diaz, as they swap homes across the Atlantic in an attempt to escape from their relationship woes, with Hollywood stars Jude Law, Jack Black, and Rufus Sewell serving as the pairs past, current, and future love interests. 

WATCH: The Holiday Trailer. Article continues after video. 

In the years following the film’s release, The Holiday has continued to gather a loyal fan following, with many eager to uncover what the cast has been up to in the nearly two decades since The Holiday was in cinemas. 

Where are the cast of The Holiday now? 

Jude Law as Graham Simpkins. (Credit: Getty)

Jude Law as Graham Simpkins

In The Holiday, Graham Simpkins lives in a countryside cottage in Surrey, England, alongside his two daughters. After his sister Iris signs up for a trans-Atlantic home swap, Graham meets Amanda Woods, and the pair’s love story begins. 

Since The Holiday, Jude Law has gone on to star in a collection of major Hollywood blockbusters, including Sherlock Holmes, The Grand Budapest Hotel, Fantastic Beasts and Where to Find Them, and Captain Marvel. 

Jude is also a father of seven, with the 50-year-old welcoming his seventh child in February 2023. 

Kate Winslet as Iris Simpkins. (Credit: Getty)

Kate Winslet as Iris Simpkins

Working as a society columnist for the Daily Telegraph, Iris Simpkins spent many years being led on by her former flame Jasper. After he announced his engagement, Iris decided to take part in the holiday home swap and ventured her way across the pond to California where she met and connected with composer Miles Dumont. 

In the years following The Holiday, Kate Winslet has gone on to become one of the most critically acclaimed stars in Hollywood, having been awarded a Grammy, Emmy, and Academy Award. 

Cameron Diaz as Amanda Woods. (Credit: Getty)

Cameron Diaz as Amanda Woods

After discovering that her boyfriend had been unfaithful, Amanda Woods trades the hustle and bustle of Los Angeles for the English countryside. Upon her arrival, Amanda meets her fellow house swap participant Iris’ brother Graham Simpkins, and the pair’s romance begins to blossom. 

In the years following The Holiday, Cameron Diaz went on to star in films such as Bad Teacher, Annie, What to Expect When You’re Expecting, and What Happens in Vegas.

Following the release of Al Gore’s 2006 film An Inconvenient Truth, Cameron worked closely with the former Presidential candidate to promote Live Earth and raise awareness for climate change. 

Jack Black as Miles Dumont. (Credit: Getty)

Jack Black as Miles Dumont

Working in Los Angeles as a music composer, Miles’ typically happy-go-lucky demeanour is challenged when he learns that his girlfriend has been cheating on him. Fortunately for Miles, the arrival of Iris Simpkins brings some sunshine back into his life, with the pair forming an immediate connection. 

Following the release of The Holiday, Jack Black continued to pursue his music career as the lead singer of Tenacious D. Jack has also continued to have a successful film career,  starring in Nacho Libre, Kung Fu Panda, and Jumanji: Welcome to the Jungle. 

In September 2018, Jack was also awarded with a star on the iconic Hollywood Walk of Fame.

Rufus Sewell as Jasper Bloom. (Credit: Getty)

Rufus Sewell as Jasper Bloom

Despite cheating on Iris, Jasper is still present in her life, with Iris’ feelings for him remaining unwavering despite his infidelity. After reconnecting, Iris eventually decides to set herself free from Jasper in order to get her “gumption” back.

Since starring in The Holiday, Rufus Sewell has starred in several series, including The Diplomat, Victoria, and The Man in the High Castle. 

In December 2023, the 56-year-old British star announced his engagement to 26-year-old Vivian Benitez, with the couple sharing the news to Instagram. 

Stream The Holiday now on Prime Video with a 30-day free trial. Subscribe here. 


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