The Holiday is a classic festive romcom featuring some big Hollywood stars – but what have they been up to since it was released in 2006?
Maria Leticia Gomes GAU Writer
08:00, 07 Dec 2025
When The Holiday hit the big screen in 2006, it quickly became a festive favourite thanks to its star-studded cast and heartwarming transatlantic love story, featuring surprise appearances from Dustin Hoffman, Lindsay Lohan, and James Franco.
Fast forward nearly two decades, and the film’s leading stars have bagged prestigious awards, headlined blockbuster franchises, embarked on entrepreneurial ventures, and started families of their own.
Let’s take a peek at what Cameron Diaz, Kate Winslet, Jude Law, Jack Black, and the rest of the main cast have been up to since this Christmas classic.
Cameron Diaz
Cameron Diaz in 2025(Image: Getty)
Cameron Diaz took on the role of Amanda Woods, the boss lady of a thriving film trailer production company based in L.A.
Post-The Holiday, she lent her voice to Princess Fiona in the Shrek series and starred in films like What Happens in Vegas with Ashton Kutcher, My Sister’s Keeper, and The Box, reports the Express.
She then shifted gears towards comedy, apart from The Green Hornet, with flicks such as Knight and Day, Bad Teacher, and What to Expect When You’re Expecting.
In 2013, she ventured into the thriller genre with Ridley Scott’s The Counselor and also wrote a health book that soared to #2 on the New York Times bestseller list.
After the release of Annie in 2014, Diaz decided to take a step back from acting to focus 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 introduced Avaline, her own brand of organic wine.
In 2022, she made a comeback to acting, starring alongside Jamie Foxx in Back in Action, and later teamed up with Keanu Reeves in Outcome. Diaz is also set to return as the voice of Fiona in Shrek 5, which is due to hit the screens in 2027.
In her personal life, Diaz has been linked to celebs like Jared Leto and Justin Timberlake. In 2015, she tied the knot with musician Benji Madden, and they now have two children – a son and a daughter.
Kate Winslet
Kate Winslet in 2025(Image: Getty)
The British actress 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 primarily recognised for her roles in period dramas, making The Holiday her first venture into romantic comedy.
Her career trajectory took an upward turn post The Holiday with lauded roles in Revolutionary Road and The Reader, bagging her Golden Globes for both, along with an Academy Award and a BAFTA for The Reader. The intense limelight led her to take a two-year break due to burnout.
Winslet made a comeback with HBO’s Mildred Pierce, earning an Emmy, followed by box office hits such as Contagion and Carnage.
After another hiatus to focus on her family, she appeared in smaller films and the Divergent trilogy. Her major resurgence came with Ammonite in 2020, considered her return to form.
Since then, she has lent her voice to documentaries, produced and starred in Lee, and featured in Avatar: The Way of Water and HBO’s The Regime.
Winslet is a passionate advocate for autism awareness, environmental conservation, and sustainable development. Her impressive accolades include seven Academy Award nominations (including one win), five BAFTAs, two Emmys, and one 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 his role in The Holiday, Jude Law had already established himself as a household name, bagging 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 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 in 2023(Image: Getty)
Already a well-known comedian and actor, Jack Black played Miles, the warm-hearted Hollywood composer who becomes Winslet’s love interest.
After dabbling in the world of romantic comedy, he gravitated back towards comedic roles across film and television, including lending his voice to Po in the Kung Fu Panda franchise.
Between 2009 to 2014, Black’s career took a bit of a breather before he bounced back into the limelight with Jumanji: Welcome to the Jungle in 2017.
Since then, he has voiced 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 Minecraft movie.
Black is a proud father of 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 was already a household name with a career spanning six decades.
Post The Holiday, Wallach continued to act well into his nineties, featuring 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 illustrious 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
After portraying Iris’ manipulative ex-boyfriend Jasper Bloom, Rufus Sewell carved out a successful career across film, television and theatre. He starred in the British crime series Zen, played one of the main characters in ITV’s Victoria, and received acclaim for his performance in The Man in the High Castle.
He also landed significant roles in films such as Dark City, The Illusionist, Old, and The Diplomat. He has been married three times and is a father to two children.
