As the seasonal story goes, two women—Amanda (Cameron Diaz) from L.A., and Iris (Kate Winslet) from England—heal their heartbreaks while home for the holidays… at each other’s homes, that is. Their respective trips across the pond inevitably lead to new romance, as they each encounter a local love interest on their respective getaways. “When people watch The Holiday, it’s just so aspirational,” Diaz told Vulture while reflecting on the movie’s charm in 2020. “They’re like, ‘One day, I’ll be able to do that.’ It’s almost like a modern-day Prince Charming, but not a helpless princess. It’s more like the fully capable princess who could have whatever she wants, but she can’t have it until she breaks open her heart and is vulnerable, and lets in the right man.” While critics panned the story as formulaic at first, the house-swapping holiday film has since gone on to cement its status as a quintessential Christmastime watch. After all, what’s cozier than a Meyers movie in the month December? As we celebrate the 16th anniversary of the 2006 film, read on for our rundown of what the cast of The Holiday is up to now.
What happened to The Holiday cast?
Kate Winslet as Iris in The Holiday
From England to Easttown! Winslet played The Holiday’s leading lady from London, a Daily Telegraph columnist who embarks on a new adventure after discovering her ex is engaged. The award-winning actress had already played several memorable parts before starring as Iris in The Holiday, including her iconic Titanic role in 1997. Since 2006, she’s continued to add to her acting resume with roles in films like Revolutionary Road, the Divergent series and 2008’s The Reader, for which she nabbed the Best Actress Oscar. She’s starred on the small screen too, most recently in her Emmy-winning role as detective Mare Sheehan in HBO’s Mare of Easttown. We’ll next see her in Avatar: The Way of Water, which premieres Dec. 16, 2022.
Cameron Diaz as Amanda in The Holiday
In the beloved rom-com, Diaz plays Amanda, a movie trailer producer from California who house swaps on a whim after discovering her boyfriend’s infidelity. In real life, Diaz went from sipping wine onscreen in The Holiday to eventually launching her own clean wine brand. While she starred in several movies after The Holiday, including comedies like What to Expect When You’re Expecting, Bad Teacher and The Other Woman, Diaz eventually retired from acting following her role in the 2014 Annie remake. In addition to marrying musician Benji Madden in 2015 and welcoming their first child, Raddix, in 2019, Diaz’s post-acting life has also included teaming up with entrepreneur Katherine Power to launch Avaline, a line of wine made with organic grapes. Following an 8-year hiatus, Diaz announced in June 2022 that she’s returning to acting in Jamie Foxx’s upcoming Netflix movie Back in Action. Foxx even called in a little help from another GOAT to explain to Diaz how to un-retire!
Jude Law as Graham in The Holiday
Law starred as Graham (aka Mr. Napkin Head), Iris’ brother. In the ultimate Meyers meet-cute, the single father falls for Amanda while she’s staying in his sister’s cozy English cottage. Law, a London native himself, has played several literary roles since the rom-com’s release, including starring in Anna Karenin and two Sherlock Holmes movies. He’s also acclaimed for his roles onstage, in the Tony-winning production of Hamlet, and on the small screen, in the HBO series The Young Pope. His most recent credits also include a role as Albus Dumbledore in Fantastic Beasts: The Secrets of Dumbledore. He’ll next hit the big screen as Captain Hook in Peter Pan & Wendy, which is slated for a 2023 release.
Jack Black as Miles in The Holiday
As Graham and Amanda’s love story unfolded, sparks were simultaneously flying between Iris and Miles, a composer played by Black. Since The Holiday, many of Black’s most memorable roles have ostensibly appealed to a younger audience. The actor is known for his voice acting as the panda Po in the Kung Fu Panda animated movies. He’s also starred in other kid-friendly films including Goosebumps, Jumanji and The Muppets. In 2018, he even cemented his status as a superstar with a star on the Hollywood Walk of Fame. He just headed back in front of the camera as iconic DJ Wolfman Jack in Weird: The Al Yankovic Story and he’ll voice Bowser in the upcoming The Super Mario Bros. Movie coming in 2023.
Rufus Sewell as Jasper in The Holiday
Sewell stars as Iris’ ex—who, despite having cheated on her, is still very much a part of her life. The two even work together at The Daily Telegraph, where Iris has perhaps the ultimate rom-com character job: writing wedding announcements. Finding out that Jasper is engaged (to the girl he cheated with, no less) leads Iris to accept Amanda’s house-swap invite, setting the plot in motion. Since his role in The Holiday, Sewell has appeared in The Tourist, Hercules, The Father and the 2021 time-warp thriller Old. He’s currently filming Netflix political thriller The Diplomat and has signed onto Jigsaw another upcoming Netflix series.
Eli Wallach as Arthur in The Holiday
Miles isn’t the only new face Iris meets in California; she also befriends Arthur Abbott, an iconic screenwriter who introduces her to films with strong female leads. The Holiday was one of Wallach’s final acting roles before he passed away in 2014 at the age of 98. Like his character, Wallach had a long, legendary career. His prolific time in Hollywood included roles in films such as The Godfather: Part III, The Good the Bad and the Ugly and The Misfits, the latter of which also starred Marilyn Monroe.
Shannyn Sossamon as Maggie in The Holiday
In one of the film’s many romantic missteps, Sossamon’s character Maggie cheats on Miles, inevitably sending him into Iris’ arms. Sossamon has starred in several indie films since, including Life Is Hot in Cracktown and The Day. In 2021, she raised $66,029 on Kickstarter for a variety show called “The Maude Room,” which she described as “a little picture show theater.” More recently, she starred in the widely panned Mexican-American thriller There Are No Saints.
Emma Pritchard as Olivia in The Holiday
Pritchard played the youngest of widower Graham’s two daughters in The Holiday, a girl who adorably begs her dad to become “Mr. Napkin Head” and loves mini marshmallows in her cocoa. Her role in the rom-com is her first and last acting credit and she doesn’t appear to have a public presence on social media.
Miffy Englefield as Sophie in The Holiday
Graham’s eldest daughter, Sophie, was played by Englefield. Although she starred in a few films after her 2006 debut in The Holiday, her last acting credit was in 2011. Now, over a decade after the holiday flick first came out, she has a daughter of her own and has switched up her style with jet-black hair. According to PEOPLE, she said in an Instagram Story on her now-deleted account that her edgier look has been a barrier to landing more roles in adulthood, writing, “As an adult, I’ve found that casting directors aren’t overly seeking people who ’look like me’ to play roles, even though body modifications [sic] isn’t rare these days and is the most common is has ever been.”
Edward Burns as Ethan in The Holiday
Burns plays Amanda’s ex-boyfriend, a California-based composer who cheats on her with his secretary at the start of the film. His real-life love story has had a much happier ending, as he’s been married to model Christy Turlington since 2003 and has welcomed two children with her. The Holiday is hardly his only romantic comedy credit, as he’s also starred in similarly feel-good flicks like 27 Dresses and Friends with Kids. Most recently, he wrote and directed the half-hour EPIX original Bridge & Tunnel. The series was canceled shortly after EPIX announced it would rebrand as MGM+.
Kathryn Hahn as Bristol in The Holiday
Hahn, now a household name, makes a small appearance in The Holiday as Bristol, Amanda’s assistant. She called her experience on-set “surreal” in an interview with RadioTimes.com, revealing that she was actually pregnant in real-life while wearing a prosthetic pregnant belly for her role. Hahn’s prolific career has included several comedies, including another (albeit much less family-friendly) holiday movie, A Bad Moms Christmas. The star, who most recently nabbed an Emmy nom for her work in the buzzy series Wandavision, has said she still watches The Holiday each year, adding, “My 15-year-old son is not as excited about it as my 12-year-old daughter!” You can see her next in Glass Onion: A Knives Out Mystery, which premieres in theaters Nov. 23 and streams Netflix Dec. 23.
John Krasinski as Ben in The Holiday
When he played Amanda’s editor Ben in The Holiday, Krasinski had just started what would become a nine-season run on The Office. In addition to his breakout role in the beloved sitcom, the actor has since starred in films including Tom Clancy’s Jack Ryan and The Quiet Place, the latter of which he also co-wrote and directed alongside wife Emily Blunt. Next, Son of a Nutcracker! 75+ Funny and Iconic Quotes from Your Favorite Christmas Movies
