Where the cast of The Holiday is now – from organic wine to Oscar wins | Films | Entertainment

When The Holiday premiered in 2006, its charming cast and cosy transatlantic romance quickly made the film a modern Christmas classic, featuring cameos from Dustin Hoffman, Lindsay Lohan, and James Franco.

Today, almost two decades later, its stars have gone on to win major awards, lead blockbuster franchises, launch businesses, and build their own families.

Here’s a look at what Cameron Diaz, Kate Winslet, Jude Law, Jack Black, and other main cast members have been up to since the holiday film.

Cameron Diaz

Cameron Diaz played Amanda Woods, the owner of a successful L.A.-based film trailer production company. Since then, she continued voicing Princess Fiona in the Shrek franchise and starred in What Happens in Vegas alongside Ashton Kutcher, My Sister’s Keeper, and The Box.

She then leaned into comedies, aside from The Green Hornet, with films such as Knight and Day, Bad Teacher, and What to Expect When You’re Expecting.

In 2013, she tried her hand at thrillers with Ridley Scott’s The Counselor and also published a health book that became a #2 New York Times bestseller.

After releasing Annie in 2014, Diaz stepped back from acting to focus on travelling, writing, and producing. She later published a second book on science and ageing in 2016 and invested heavily in health and biotech startups. Diaz also launched Avaline, her organic wine brand.

She returned to acting in 2022, starring opposite Jamie Foxx in Back in Action, and later worked with Keanu Reeves in Outcome. Diaz is also confirmed to reprise her voice role as Fiona in Shrek 5, scheduled for release in 2027.

In her personal life, Diaz previously dated stars including Jared Leto and Justin Timberlake. In 2015, she married musician Benji Madden, with whom she has two children – a son and a daughter.

Kate Winslet

British actress Kate Winslet played Iris Simpkins, a London-based society columnist who escapes to the U.S. to recover from a toxic office romance.

At that point in her career, Winslet was primarily known for her roles in period dramas, making The Holiday her first romantic comedy.

Her career soared even higher afterwards with acclaimed roles in Revolutionary Road and The Reader, earning her Golden Globes for both, as well as an Academy Award and a BAFTA for The Reader. The intense spotlight led her to take a two-year hiatus due to burnout.

Winslet returned with HBO’s Mildred Pierce, earning an Emmy, followed by commercial successes such as Contagion and Carnage.

After another break to focus on raising her children, she appeared in smaller films and the Divergent trilogy. Her major resurgence came with Ammonite in 2020, considered her return to form.

She has since narrated documentaries, produced and starred in Lee, and appeared in Avatar: The Way of Water and HBO’s The Regime.

Winslet is active in autism awareness, environmental issues, and sustainable development. She has earned seven Academy Award nominations (including one win), five BAFTAs, two Emmys, and one Grammy.

She has three children: Mia (with Jim Threapleton), Joe (with Sam Mendes), and Bear (with Abel Smith).

Jude Law

Jude Law had already become a major name before The Holiday, earning Golden Globe and Academy Award nominations for The Talented Mr Ripley.

After playing Graham, the charming widowed father, he returned to the stage in the West End, taking on the title role in Hamlet.

He later starred as Dr Watson in Sherlock Holmes alongside Robert Downey Jr. and delivered standout 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 took on roles 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 shares three children with actress Sadie Frost, one with model Samantha Burke, one with Catherine Harding, and two with Phillipa Coan.

Jack Black

Jack Black, already a well-known comedian and actor, played Miles, the warm-hearted Hollywood composer who becomes Winslet’s love interest.

After his venture into romantic comedy, he returned mostly to comedic roles across film and television, including extensive voice work such as Po in the Kung Fu Panda franchise.

From 2009 to 2014, Black saw a quieter period in his career before returning to mainstream success with Jumanji: Welcome to the Jungle in 2017.

Since then, he has voiced Bowser in The Super Mario Bros. Movie, appeared in The Mandalorian, starred in Kung Fu Panda 4, and joined the cast of the upcoming Minecraft movie.

Black shares two sons with Tanya Haden and describes himself as an atheist, culturally Jewish individual.

Eli Wallach

The veteran actor played Arthur Abbott, a retired Hollywood screenwriter who befriends Winslet’s Iris. He had already made his name with a six-decade-spanning career.

After The Holiday, Wallach continued to act into his nineties, appearing in films such as 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 passed away peacefully at 98 in 2014, leaving behind his wife, Anne Jackson, and three children.

Rufus Sewell

After playing Iris’ manipulative ex-boyfriend Jasper Bloom, Rufus Sewell built a strong career across film, television and theatre. He starred in British crime series Zen, played one of the main characters in ITV’s Victoria, and was praised for his performance in The Man in the High Castle.

He also had major roles in films like Dark City, The Illusionist, Old, and The Diplomat. He has been married three times and has two children.