‘The Holiday’ Cast: Where Are They Now?

Credit: Simon Mein/Sony/Kobal/Shutterstock; Zade Rosenthal/Sony/Kobal/Shutterstock

‘The Holiday’ Cast: Where Are They Now?

Spontaneous travel, Christmas cheer, dueling love stories — The Holiday has it all! Cameron Diaz and Kate Winslet were already majorly famous before they starred in the 2006 film, but it is still one of their most beloved projects (for good reason).

The Nancy Meyers-directed movie follows two unlucky-in-love women who trade houses for the holiday season. Of course, romance ensues for Amanda (Diaz) and Iris (Winslet) in the form of Graham (Jude Law) and Miles (Jack Black), respectively.

While the romantic comedy stayed on fans’ minds for years to come and became a staple many rewatch every time Christmas rolls around, Black hilariously forgot about its very existence in December 2019.

“My favorite holiday film — it’s got to be Elf,” the actor told Variety at the time. “Jon Favreau — I don’t know if I’m saying it right — and Will Ferrell just knocking it out of the park.”

The interviewer then teased Black about his selection: “You could have said your own movie.”

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The Jumanji: The Next Level star looked confused before admitting defeat. “Do I have a Christmas movie? Which one is mine?” he asked. “Oh, The Holiday! Obviously, The Holiday! Nancy Meyers — genius.”

“Holiday” is literally in the title, but who could blame him for the temporary lapse? 2006 was a while ago.

Black has been so busy since The Holiday that he can’t even remember starring in it, but Diaz, on the other hand, took a step back from the business. “I am actually retired,” she confirmed in an Entertainment Weekly interview published in March 2018.

The Charlie’s Angels star elaborated on her decision in August 2019. “I started [experiencing fame] when I was 22, so 25 years ago — that’s a long time,” she told InStyle. “The way I look at it is that I’ve given more than half of my life to the public. I feel it’s OK for me to take time for myself now to reorganize and choose how I want to come [back] into the world. If I decide to. I don’t miss performing.”

She came out of retirement in for Netflix’s Back In Action with Jamie Foxx, which was announced in June 2022.

“It just turned out that at this point in time, it’s a really nice thing for my family,” Diaz said during a September 2022 appearance on The Rachael Ray Show. “My husband [Benji Madden] is the best. He’s so supportive. He really wants to help me. He’s been busy building his businesses for the last eight years, and he appreciates the support that I’ve given him in that and he really wants to be able to show me that support. So he’s gonna come along with our daughter and we’re gonna all go together and make a movie in the U.K.”

Scroll through the gallery below to see what the stars of The Holiday have been up to!

Credit: Simon Mein/Sony/Kobal/Shutterstock; Evan Agostini/Invision/AP/Shutterstock

Cameron Diaz (Amanda)

Diaz went on to star in What Happens in Vegas, My Sister’s Keeper, Knight and Day, Bad Teacher, What to Expect When You’re Expecting, The Other Woman and Annie before retiring from acting. She launched a line of clean, organic wines called Avaline in 2020 and released The Body Book in 2013 and The Longevity Book in 2016. She returned to acting in 2022 for Netflix’s Back in Action.

The actress married Benji Madden in January 2015. They announced the arrival of daughter Raddix in January 2020.

Credit: Simon Mein/Sony/Kobal/Shutterstock; Sundholm Magnus/Action Press/Shutterstock

Kate Winslet (Iris)

The Oscar winner stayed busy with roles in The Reader, Revolutionary Road, Mildred Pierce, Divergent, Steve Jobs and The Mountain Between Us, racking up awards along the way. In 2021, she won an Emmy for best actress in a limited series for her role in HBO’s Mare of Easttown.

Winslet shares daughter Mia with ex-husband Jim Threapleton, son Joe with ex-husband Sam Mendes and son Bear with husband Edward Abel Smith (formerly known as Ned Rocknroll), whom she wed in December 2012.

Credit: Zade Rosenthal/Sony/Kobal/Shutterstock; Arthur Mola/Invision/AP/Shutterstock

Jude Law (Graham)

Law has starred in many films since The Holiday, including Anna Karenina, The Grand Budapest Hotel, Spy and Captain Marvel, as well as HBO series The Young Pope and The New Pope. He plays Albus Dumbledore in the Fantastic Beasts franchise and John Watson in Sherlock Holmes franchise.

The father of six has three children with ex-wife Sadie Frost, a daughter with ex Samantha Burke, a daughter with ex Catherine Harding and a child with wife Phillipa Coan, whom he married in May 2019.

Credit: Zade Rosenthal/Sony/Kobal/Shutterstock; Matt Baron/Shutterstock

Jack Black (Miles)

The Golden Globe nominee moved on to Kung Fu Panda, Tropic Thunder, Gulliver’s Travels, Bernie, Goosebumps, Jumanji: Welcome to the Jungle and The House With a Clock in Its Walls. He is also the lead vocalist of the duo Tenacious D. 

Black tied the knot with Tanya Haden in March 2006. They are parents of sons Samuel and Thomas.

Credit: Zade Rosenthal/Sony/Kobal/Shutterstock

Eli Wallach (Arthur)

Wallach appeared in Mama’s Boy, Nurse Jackie, Wall Street: Money Never Sleeps and The Ghost Writer before his death in June 2014 at age 98. He was survived by three children, three grandchildren and one great-grandchild.

Credit: Charles Sykes/Shutterstock; Ken McKay/ITV/Shutterstock

Rufus Sewell (Jasper)

Sewell starred in The Man in the High Castle, Victoria, Eleventh Hour, The Tourist, Judy and The Marvelous Mrs. Maisel. 

The actor shares son William with ex-wife Amy Gardner and daughter Lola with Ami Komai.

Credit: Erik Pendzich/Shutterstock; Gregory Pace/Shutterstock

Edward Burns (Ethan)

Burns went on to appear in 27 Dresses, Entourage, Friends With Kids, Alex Cross and Public Morals. He also produces, writes and directs many of his projects, including the Epix series Bridge and Tunnel and the film Summer Days, Summer Nights.

The actor married Christy Turlington in June 2003. The couple are parents of daughter Grace and son Finn.

Credit: Sipa/Shutterstock; Matt Baron/BEI/Shutterstock

Shannyn Sossamon (Maggie)

The actress went on to appear in several episodes of the TV shows Mistresses, Sleepy Hollow and Wayward Pines. She also starred in the movies Wristcutters: A Love Story, Our Family Wedding and The Undertaker’s Wife.

She welcomed son Audio with ex Dallas Clayton in 2003 and son Mortimer with ex Richard Purser in 2011.