The Holiday stars 18 years on from festive film’s release – sad death, Oscar joy and new career

The Holiday became a festive favourite when it was released in 2006, and nearly two decades later, its stars including Cameron Diaz, Kate Winslet, Jude Law and Jack Black have achieved remarkable things

When The Holiday hit the screens in 2006, its delightful cast and heartwarming cross-Atlantic love story quickly established the film as a contemporary Christmas favourite, featuring guest appearances from Dustin Hoffman, Lindsay Lohan, and James Franco.

Fast forward nearly twenty years, and its stars have bagged major awards, headlined blockbuster franchises, started businesses, and built their own families. Let’s take a peek at what Cameron Diaz, Kate Winslet, Jude Law, Jack Black, and other main cast members have been up to since the festive flick.

Cameron Diaz

Cameron Diaz in 2025(Image: Getty)

Cameron Diaz portrayed Amanda Woods, the proprietor of a thriving film trailer production company based in L.A. After The Holiday, she continued lending her voice to Princess Fiona in the Shrek series and starred in What Happens in Vegas with Ashton Kutcher, My Sister’s Keeper, and The Box, according to the Express.

She then gravitated towards comedies with films like Knight and Day, Bad Teacher, and What to Expect When You’re Expecting. In 2013, she ventured into thrillers with Ridley Scott’s The Counselor and also penned a health book that clinched the #2 spot on the New York Times bestseller list.

After releasing Annie in 2014, Diaz took a step back from acting to concentrate on travelling, writing, and producing. She later published a second book on science and ageing in 2016 and made significant investments in health and biotech startups. Diaz also launched Avaline, her organic wine brand.

In 2022, she made a triumphant return to acting, sharing the screen with Jamie Foxx in Back in Action and later collaborating with Keanu Reeves in Outcome. Diaz is also set to lend her voice once again to Fiona in Shrek 5, slated for release in 2027. Off-screen, Diaz has been linked romantically to celebrities such as Jared Leto and Justin Timberlake. In 2015, she tied the knot with musician Benji Madden, and they now share two children – a son and a daughter.

Kate Winslet

Kate Winslet in 2025(Image: Getty)

British star Kate Winslet portrayed Iris Simpkins, a society columnist based in London who flees to the U.S. to heal from a toxic office romance. At this stage in her career, Winslet was predominantly recognised for her performances in period dramas, making The Holiday her debut in the romantic comedy genre.

Her career trajectory took an upward turn after The Holiday, with critically acclaimed roles in Revolutionary Road and The Reader, earning her Golden Globes for both, along with an Academy Award and a BAFTA for The Reader. The relentless spotlight led her to take a two-year break due to exhaustion.

Winslet made a comeback with HBO’s Mildred Pierce, which earned her an Emmy, followed by box office hits like Contagion and Carnage. After another hiatus to focus on her family, she featured in smaller films and the Divergent trilogy. Her significant comeback was marked by Ammonite in 2020, hailed as her return to form.

Since then, she has lent her voice to documentaries, produced and starred in Lee, and appeared in Avatar: The Way of Water and HBO’s The Regime. Winslet is a vocal advocate for autism awareness, environmental conservation, and sustainable development. Her impressive accolades include seven Academy Award nominations (with one win), five BAFTAs, two Emmys, and a Grammy. She is a mother to three children: Mia (with Jim Threapleton), Joe (with Sam Mendes), and Bear (with Abel Smith).

Jude Law

Jude Law in 2025(Image: Getty)

Before The Holiday, Jude Law had already made his mark, earning Golden Globe and Academy Award nominations for The Talented Mr Ripley. After portraying the endearing widowed father Graham, he returned to the West End stage, taking on the title role in Hamlet.

He later starred as Dr Watson in Sherlock Holmes alongside Robert Downey Jr., and delivered memorable performances in Contagion, The Young Pope, Fantastic Beasts: The Crimes of Grindelwald, and appeared as a screenwriter in Woody Allen’s A Rainy Day in New York. He also featured in Marvel’s Captain Marvel, Peter Pan & Wendy, and Star Wars: Skeleton Crew.

Law has been active in peace efforts in Afghanistan and anti-fur campaigns, and was featured on Vampire Weekend’s 2019 album Father of the Bride. He is a father to three children with actress Sadie Frost, one with model Samantha Burke, one with Catherine Harding, and two with Phillipa Coan.

Jack Black

Jack Black in 2023(Image: Getty)

Already a renowned comedian and actor, Jack Black played Miles, the affable Hollywood composer who becomes Winslet’s love interest. After dabbling in romantic comedy, he primarily returned to comedic roles in film and television, including significant voice work such as Po in the Kung Fu Panda franchise.

From 2009 to 2014, Black experienced a quieter phase in his career before bouncing back to mainstream success with Jumanji: Welcome to the Jungle in 2017. Since then, he has lent his voice to Bowser in The Super Mario Bros. Movie, made an appearance in The Mandalorian, starred in Kung Fu Panda 4, and joined the cast of the forthcoming Minecraft movie. Black is a father to two sons with Tanya Haden and identifies himself as an atheist, culturally Jewish individual.

Eli Wallach

The seasoned actor portrayed Arthur Abbott, a retired Hollywood screenwriter who strikes up a friendship with Winslet’s Iris. He had already established his name with a career spanning six decades. Post The Holiday, Wallach continued to act into his nineties, featuring in films like The Ghost Writer and Wall Street: Money Never Sleeps, and making notable TV appearances. He received numerous lifetime achievement awards throughout his career, including an Academy Honorary Award in 2011. Wallach peacefully passed away at the age of 98 in 2014, leaving behind his wife, Anne Jackson, and three children.

Rufus Sewell

Following his role as Iris’ manipulative ex-boyfriend Jasper Bloom, Rufus Sewell built a robust career across film, television and theatre. He starred in the British crime series Zen, played a key character in ITV’s Victoria, and received acclaim for his performance in The Man in the High Castle. He also held significant roles in films such as Dark City, The Illusionist, Old, and the TV series, The Diplomat. He has walked down the aisle three times and is a father to two children.