'The Holiday' Cast: Where Are They Now?

When it comes to romantic holiday movies, nothing quite tops The Holiday.

Starring Kate Winslet and Cameron Diaz, the 2006 Nancy Meyers film follows two women who decide to switch homes (and continents) for the holidays after facing major heartbreak. What ensues is a heartwarming tale as they each find love with new people (Jack Black and Jude Law) over Christmas. The film premiered in New York City on Nov. 29, 2006, before it was theatrically released on Dec. 8, 2006, and has since become a classic over the years.

"People look at Nancy's movies as a statement, in a way," Diaz told Vulture about the film in 2020. "It's set in the real world, but it's like, Who's getting on first class, and flying, and taking this cute little cottage in the middle of England? Who gets to do that? You always wish that was you. You want to go do that."

She added, "When people watch The Holiday, it's just so aspirational. 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. And not just Prince Charming, but the guy who's actually capable of showing up in all the ways she needs him to."

See what the cast has been up to since The Holiday was released.

Jude Law as Graham Simpkins

Before Law played sensitive, bookish, single father Graham (a.k.a. Mr. Napkin Head), the two-time Oscar nominee was already revered for his work on the screen and stage.

No stranger to adventure and fantasy films, Law is known for his role as Dr. Watson in 2009's Sherlock Holmes and its 2011 sequel. He appeared as the alien military commander Yon-Rogg in 2019's Captain Marvel and was featured as young Albus Dumbledore in the second and third installments of the Fantastic Beasts franchise. Law also starred as Captain Hook in the 2023 Disney+ live-action movie adaptation of Peter Pan and Wendy.

Law has achieved success on the small screen as well, most notably on the HBO series The Young Pope, The New Pope and The Third Day. In 2018, the actor earned a Golden Globe nomination for his performance as Lenny Belardo on The Young Pope. Law is also gearing up to portray a Jedi on the Disney+ series Star Wars: Skeleton Crew in 2024.

Beyond acting, he is actively involved with UNICEF and philanthropy related to climate change and cancer research. Law married psychologist Phillipa Coan in a low-key ceremony in London in 2019, and he's the father of seven children: He and Coan welcomed two kids together. He shares two sons — Rafferty and Rudy — and daughter Iris with ex-wife Sadie Frost. Law has two more daughters, Sophia and Ada, from previous relationships.

Cameron Diaz as Amanda Woods

As one of Meyers' leading ladies, Diaz played Amanda, the Los Angeles movie trailer executive who breaks her famous promise not to fall in love with Graham. Fresh off the heels of The Holiday and critically acclaimed performances in 2009's My Sister's Keeper and 2010's Knight and Day, the actress transitioned into comedy — starring in films like Bad Teacher (2011), What to Expect When You're Expecting (2012), The Other Woman (2014) and Sex Tape (2014). Diaz is also known for voicing the animated character Princess Fiona in the Shrek franchise.

Following her role in the 2014 remake of Annie, where she assumed the role of selfish orphanage owner Miss Hannigan, Diaz said she was retiring from acting. However, in June 2022, she announced her return to the screen with the upcoming Netflix flick Back in Action, which is set to be released in 2024 and features her former Annie costar, Jamie Foxx.

During her time off-screen, Diaz has focused mainly on wellness and food ventures. In 2016, she published The Longevity Book: The Science of Aging, the Biology of Strength, and the Privilege of Time (a follow-up to 2013's The Body Book: The Law of Hunger, the Science of Strength, and Other Ways to Love Your Amazing Body), a New York Times best seller. Diaz invested in health and biotech startups like Modern Acupuncture and Seed Health, and, in 2022, she co-launched an organic wine brand: Avaline.

Diaz has been married to Good Charlotte musician Benji Madden since January 2015, and the couple welcomed their first child, daughter Raddix, in December 2019.

Kate Winslet as Iris Simpkins

By the time Winslet played Iris — a witty wedding columnist for the Daily Telegraph — she had already achieved notoriety as Rose in 1997's Titanic and blue-haired Clementine in 2004's Eternal Sunshine of The Spotless Mind, for which she earned an Oscar nomination for Best Actress. (Nearly a decade after playing star-crossed lovers in James Cameron's Titanic, Winslet and Leonardo DiCaprio reunited on-screen in 2008's Revolutionary Road. She played the strong-willed housewife April, receiving a Golden Globe for best actress.)

Winslet later gave an Oscar-nominated performance in 2006's Little Children before winning Best Actress for 2008's The Reader. In 2016, she nabbed another Oscar nomination for her role as Apple marketing executive Joanna Hoffman in Steve Jobs. Winslet also appeared in the first and second installments of the Divergent franchise as villain Jeanine Matthews. The 2017 survival drama The Mountain Between Us, costarring Idris Elba, featured Winslet as photojournalist Alex Martin.

In 2021, she executive produced and starred on HBO's Mare of Easttown, adopting Pennsylvania's Delaware County accent to play a grieving murder detective. Winslet won an Emmy, Golden Globe and SAG Award for her performance as the titular Mare Sheehan. The actress then stepped into a motion capture suit (and held her breath for more than five minutes!) to play Na'vi warrior Ronal in 2022's Avatar: The Way of Water — her second project with filmmaker Cameron. She is slated to reprise the role in an upcoming third installment of the Avatar film series.

Off-screen, Winslet is an advocate for autism awareness. In 2010, she co-founded the nonprofit Golden Hat Foundation to shed light on the strengths and abilities of people with autism. She authored The Golden Hat: Talking Back to Autism, which the United Nations featured during a ceremony on World Autism Awareness Day in April 2012.

In 2012, Winslet and Richard Branson's nephew, Edward Abel Smith, tied the knot. The couple welcomed their son, Bear Blaze, in 2013. Winslet shares older son Joe (born in 2003) with American Beauty director Sam Mendes. The two split in 2011. Winslet also has a daughter, Mia, with her ex-husband and director Jim Threapleton, whom she was married to from 1998 to 2001.

Jack Black as Miles Dumont

Before starring in the holiday rom-com as Hollywood composer Miles, Black was already famous for his roles as Barry in High Fidelity (2000), stoner Lance in Orange County (2002) and substitute teacher–turned–middle school music hero Dewey Finn in School of Rock (2003).

He followed up The Holiday with 2010's Gulliver's Travels — costarring Jason Segel and Emily Blunt — as the titular character whose fibs lead him to the Bermuda Triangle. Later, Black acted in two Goosebumps movies, Jumanji: Welcome to the Jungle (and the 2019 sequel) and cameoed as Wolfman Jack in 2022's Weird: The Al Yankovic Story. Beginning in 2008, Black lent his voice to the Kung Fu Panda franchise as the fluffy protagonist Po, and in 2023, he voiced the fire-breathing Bowser in The Super Mario Bros. Movie. He is also set to voice Claptrap in the upcoming film adaptation of the popular video game Borderlands. On TV, the actor has appeared on comedy shows like Drunk History, The Brink and History of the World: Part II.

Black is one half of the bearded comedy rock duo Tenacious D with collaborator Kyle Gass. The band has released four studio albums: Tenacious D (2001), The Pick of Destiny (2006), Rize of the Fenix (2012) and Post-Apocalypto (2018). In 2015, they brought home a Grammy for best metal performance for "The Last in Line."

In August 2006, Black founded a production company — Electric Dynamite Productions, Inc. — which produced the 2021 dark comedy Happily featuring Joel McHale. He also launched the YouTube channel JablinskiGames in December 2018, showcasing his gaming skills and comedy sketches.

Black married musician Tanya Haden in March 2006. Together, they share sons Samuel Jason and Thomas David.

Rufus Sewell as Jasper Bloom

Since playing Iris' cheating ex, Jasper, Rufus Sewell has made a name for himself both in Hollywood and on stage, appearing in the movies The Tourist (2010), Abraham Lincoln: Vampire Hunter (2012), Hercules (2014), Judy (2019) and M. Night Shyamalan's Old (2021). He notably led the cast of the British play Rock 'n' Roll, in its West End and Broadway productions, alongside Succession star Brian Cox. For Sewell's role as Jan, he received his first-ever Tony Award nomination in 2008.

In 2008, Sewell portrayed Alexander Hamilton in the HBO miniseries John Adams. He followed that up with a starring role on CBS' Eleventh Hour as Dr. Jacob Hood — a biophysicist and science adviser to the FBI. After a guest appearance on The Marvelous Mrs. Maisel, Sewell earned an Emmy nomination in 2019 for his performance.

He was also featured on the British historical drama Victoria and a regular on the Amazon Prime Video dystopian series The Man in the High Castle. As of 2023, Sewell has led the cast of Netflix's heist anthology Kaleidoscope and political thriller The Diplomat, starring opposite Keri Russell as her on-screen husband, Hal Wyler.

In December 2023, Sewell became engaged to actress Vivian Benitez. The actor shares a daughter, Lola, with ex-girlfriend Ami Komai and a son, William Douglas, with ex-wife Amy Gardner — whom he divorced in 2006.

Shannyn Sossamon as Maggie

After playing Maggie, an aspiring actress and Miles' unfaithful girlfriend, Shannyn Sossamon landed several roles in indie and horror films. She appeared in One Missed Call (2008), Life Is Hot in Cracktown (2009), The Day (2011), Sinister 2 (2015) and Grimcutty (2022).

Sossamon was a series regular on the supernatural romance Moonlight, playing 340-year-old vampire Coraline, and she appeared on Fox's Wayward Pines as Matt Dillon's on-screen wife. Her other TV credits include How to Make It in America, Mistresses and Sleepy Hollow, the latter of which she played Pandora, a mysterious woman who arrives in town having captured the Headless Horseman.

Beyond acting, Sossamon was the frontwoman and drummer for the rock band Warpaint started with her sister, Jenny Lee Lindberg.

The actress has two sons — Audio Science and Mortimer.

Emma Pritchard as Olivia Simpkins

Emma Pritchard hasn't appeared on-screen since playing Law's younger daughter, Olivia, who famously asks her father to "do Mr. Napkin Head." Her role in The Holiday is Pritchard's only documented acting credit.

Miffy Englefield as Sophie Simpkins

Miffy Englefield has enjoyed a couple of minor roles on TV shows like The Whistleblowers and Casualty since portraying Law's older daughter, Sophie. She also appeared in the 2011 short film Beautiful Enough.

Since then, she has kept a relatively low profile, absent her life updates as a mother and punk rock musician on TikTok. Englefield revealed to The New York Times in November 2019 that she works as a barista between music gigs.

In 2020, Englefield and her partner, Alex Whivley-Conway, welcomed daughter Frances Rosanna Lee — who, according to the actress, doesn't recognize her in The Holiday. "[My daughter’s] seen it. She was a bit confused why I had ginger hair and I wasn’t the darker-haired one, seeing as I’ve had black hair her whole life," she told Metro.co.uk in 2023. "If you ask her now what film mummy was in she’s like, 'The Holiday,' which is lovely."

Englefield continued, "My family and friends like to see it as just a constant running joke to bring it up as much as possible to embarrass me around Christmas."

Eli Wallach as Arthur Abbott

Eli Wallach was already a veteran actor — appearing in The Magnificent Seven (1960), The Misfits (1961) and The Good, the Bad and the Ugly (1966) — before charming festive movie lovers as Arthur, Amanda's neighbor and an award-winning screenwriter. Following The Holiday, Wallach was featured in New York, I Love You (2008) and Wall Street: Money Never Sleeps (2010).

He earned Emmy nominations for his guest appearances on Studio 60 on the Sunset Strip in 2007 and Nurse Jackie in 2010. In 2011, Wallach received an Honorary Academy Award for his decades-long contributions to the film industry.

The actor's final role was in 2015's The Train, a short film where he played a Holocaust survivor and mentor to a young man. The short premiered at the Rhode Island International Film Festival after Wallach's death.

Wallach was married to actress Anne Jackson from 1948 until his death in June 2014. The couple shared three children, Peter, Roberta and Katherine. He died at age 98 of natural causes.