'The Holiday' Cast: Where Are They Now?

Hello, Mr. Napkin Head! See what the star-studded cast of Nancy Meyers' romantic comedy has been up to since its 2006 premiere

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 romantic comedy hit theaters.

Jude Law as Graham Simpkins

Decades after Law played sensitive, bookish, single father Graham (a.k.a. Mr. Napkin Head), he has remained an adored figure on screen and stage. After the success of the Nancy Meyers classic, Law went on to star as Dr. Watson in Sherlock Holmes and its sequel, Sherlock Holmes: A Game of Shadows (2009, 2011), and appeared in Wes Anderson's The Grand Budapest Hotel (2014).

The rom-com veteran is no stranger to the fantasy world either. Law took on the role of alien military commander Yon-Rogg in Captain Marvel (2019) and was featured as a young Albus Dumbledore in the second and third Fantastic Beasts and Where to Find Them films (2018, 2022). In 2023, the actor put on his pirate hat to play Captain Hook in Disney+'s Peter Pan and Wendy, and he's set to star as a Jedi in Disney+'s Star Wars: Skeleton Crew in 2023.

In 2009, Law took on the titular role of Hamlet in a West End production that made its way to Broadway months later. He was nominated for a Drama Desk Award and Tony Award and won a Critics' Choice Award for best Shakespearean performance. In 2007, Law received an Honorary César Award and was named a knight of the Order of Arts and Letters by the French government.

The actor received praise for his role as the stubborn Pope Pius XIII on HBO's The Young Pope, which he reprised in the series' 2020 continuation, The New Pope. Later that year, he starred in HBO's psychological thriller, The Third Day as Sam — a grieving father navigating a mysterious island — opposite actress Katherine Waterston.

Outside of acting, the star has been involved with UNICEF and philanthropy related to climate change and cancer research.

Law shares two sons and a daughter with ex-wife Sadie Frost (Rafferty, Rudy and Iris) and daughters with ex-girlfriends Samantha Burke (Sophia) and Catherine Harding (Ada), respectively. He married his wife Phillipa Coan in 2019, with whom he shares a daughter born in 2020.

Cameron Diaz as Amanda Woods

Diaz starred as Amanda, the Los Angeles movie trailer producer who breaks her famous promise not to fall in love with Graham. Coming off of several critically acclaimed dramatic roles in films like Being John Malkovich (1999), Gangs of New York (2002) and My Sister's Keeper (2009), Diaz transitioned to mostly comedy in the early 2010s.

She starred in funny flicks like Bad Teacher (2011) and its subsequent TV spinoff as the bad teacher herself — the somewhat spiraling Elizabeth Halsey. She played alongside Leslie Mann and Kate Upton in The Other Woman (2014) and opposite Jason Segel in Sex Tape (2014).

Following her role in the 2014 remake of Annie, where she played Miss Hannigan — the orphanage owner with a serious distaste for little girls — Diaz announced that she was retiring from acting.

During her time offscreen, Diaz focused mainly on wellness and food ventures. In June 2016, she published The Longevity Book (a follow-up to 2013's The Body Book), which landed the #2 spot on the New York Times Best Seller list. Diaz invested in health and biotech startups like Modern Acupuncture and Seed Health, and in 2022, she co-launched an organic wine brand: Avaline.

In June 2022, it was announced that Diaz would return to acting with Netflix action-comedy Back in Action alongside her Annie costar, Jamie Foxx.

Diaz married musician Benji Madden in 2015, and the couple welcomed their first child, Raddix, in 2019.

Kate Winslet as Iris Simpkins

By the time Winslet played Iris, a wittyDaily Telegraph columnist, she was already a Hollywood A-lister. She is considered one of her generation's most gifted actresses and, in 2012, was appointed Commander of the Order of the British Empire (CBE) for her contributions to drama.

Before The Holiday, two of Winslet's most iconic roles were in Titanic (1997) as Rose opposite Leonardo DiCaprio and Eternal Sunshine of The Spotless Mind (2004) as blue-haired Clementine opposite Jim Carrey. Winslet reunited with Leonardo DiCaprio in 2008's Revolutionary Road as April, a strong-willed 1950's housewife, and her performance won her a Golden Globe for best actress.

Winslet went on to star in Little Children (2006) and The Reader (2008), which respectively earned her an Oscar nomination and win for Best Actress. She also appeared in the first and second Divergent movies (2014, 2015) as antagonist Jeanine Matthews and in The Mountain Between Us (2017) as photojournalist Alex Martin opposite Idris Elba.

In 2021, she executive produced and starred on HBO's Mare of Easttown, where she adopted a Delaware County accent to play a grieving murder detective alongside her partner, portrayed by Evan Peters. 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 seven and a half minutes straight!) to play aquatic Na'vi, Ronal, in 2022's Avatar 2: The Way of Water — her second project with Titanic director James Cameron. She is slated to reprise the role in an upcoming third installment of the Avatar series.

Off-screen, Winslet is an advocate for autism awareness. In 2010, she co-founded the Golden Hat Foundation, which aims 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 2012.

Winslet shares her daughter Mia (an actress) with her ex-husband, director Jim Threapleton, and her son Joe with her ex-boyfriend, director Sam Mendes. In 2012, Winslet married Edward Abel Smith, and the two welcomed their son, Bear, in 2013.

Jack Black as Miles Dumont

Black was already a familiar face when he played Hollywood composer Miles. Some of the funnyman's most loved roles of the early 2000s include 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 Gulliver's Travels (2010) — alongside Segel and Emily Blunt — as the titular Gulliver whose fibs lead him to the Bermuda Triangle. Later, Black acted in two Goosebumps movies (2015, 2018), Jumanji and its sequel (2017, 2019) and Weird: The Al Yankovic Story (2022).

Beginning in 2008, Black lent his voice to the Kung Fu Panda franchise as fluffy protagonist Po Ping, and in 2023, he voiced the fire-breathing Bowser in The Super Mario Bros. Movie. The actor has also made appearances on a handful of TV shows like The Office and iCarly.

Black is one half of the comedy/hard rock duo Tenacious D, alongside collaborator Kyle Gass. The band has released four albums: The Pick of Destiny, Rize of the Fenix and Post-Apocalypto, and won best metal performance at the 57th Grammy Awards.

In 2006, Black founded a production company, Electric Dynamite Productions, Inc, which produced the comedy thriller Happily (2021) starring Joel McHale. He also runs a popular YouTube channel, Jablinski Games, which often centers on comedy sketches and gaming with his two sons.

Black married musician Tanya Haden in 2006, with whom he shares two sons: Samuel Jason and Thomas David, born in 2006 and 2008.

Rufus Sewell as Jasper Bloom

Since playing Iris' less-than-honest ex, Jasper, Rufus Sewell has made a name for himself on the big screen, small screen and stage. He went on to appear in Paris je t'aime (2006), Abraham Lincoln: Vampire Hunter (2012), Judy (2019) and M. Night Shyamalan's Old (2021).

In 2008, Sewell portrayed Alexander Hamilton on HBO's miniseries John Adams, which he followed with a starring role on CBS' Eleventh Hour as Dr. Jacob Hood — a biophysicist and Special Science Adviser to the FBI. He guest starred on an episode of The Marvelous Mrs. Maisel in 2018, for which he received an Emmy nomination for outstanding guest actor in a comedy series. Sewell played John Smith, a former US Army Captain turned Nazi leader on Man in The High Castle.

In 2023, Sewell starred in Netflix's heist anthology series, Kaleidoscope, and The Diplomat as Hal Wyler, opposite Keri Russell.

He notably led the cast of the British play Rock 'n' Roll, in its West End and Broadway productions, alongside Succession superstar Brian Cox. For Sewell's role as Jan, he was nominated for a Tony Award and won a Laurence Olivier Award for best actor in a play.

Sewell shares a son, William Douglas, with his ex-wife: producer Amy Gardner. He shares a daughter, Lola, with his partner, Ami Komai.

Shannyn Sossamon as Maggie

After playing Maggie, Miles' aspiring-actress girlfriend, Shannyn Sossamon landed numerous TV and film roles — mainly in independent features and horror flicks. She appeared in movies like 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 CBS' Moonlight — a supernatural romance where she played a 340-year-old vampire, Coraline, and appeared on Fox's Wayward Pines as Matt Dillon's onscreen wife. In Fox's hit series Sleepy Hollow, Sossamon was Pandora, a mysterious woman who arrives in town having captured the Headless Horseman.

Outside of acting, Sossamon is involved in music. She started the indie/psychedelic rock band Warpaint with her sister, where she played the drums and sang.

The actress has two sons — Audio Science and Mortimer.

Emma Pritchard as Olivia Simpkins

Emma Pritchard hasn't appeared on-screen since playing one of Law's young daughters, Olivia. Her role in The Holiday is Pritchard's only documented acting credit.

Miffy Englefield as Sophie Simpkins

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

Now a young adult, Englefield is a part of the punk scene in West Sussex, UK, where she balances gigging with working as a barista.

In 2020, Englefield welcomed a daughter, Frances Rosanna Lee, with her partner, Alex Whivley-Conway.

Eli Wallach as Arthur Abbott

Eli Wallach already had a notable resume before starring as Arthur, Amanda's neighbor who happens to be an award-winning screenwriter. In the '60s, the beloved actor played alongside Marilyn Monroe and Clark Gable in The Misfits (1961) and appeared in classics like The Good, The Bad and The Ugly (1966) and Once Upon a Time in the West (1968). Wallach continued to act well into his nineties and, following The Holiday, was featured in New York I Love You (2008) and Wall Street: Money Never Sleeps (2010).

In 2011, Wallach was presented with an Honorary Academy Award for his decades-long contributions to the film industry.

The actor's final role was in 2015'sThe 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.

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