The Holiday Turns 15 This Year: See Where the Cast Is Now

·4 min read
The Holiday then and now
The Holiday then and now

Simon Mein/Sony/Kobal/Shutterstock

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 holiday classic over the years.

"People look at Nancy's movies as a statement, in a way," Diaz told Vulture about the film. "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."

In honor of the film's 15th anniversary this year, see what the cast is up to now.

Jude Law

The Holiday then and now
The Holiday then and now

Moviestore/Shutterstock; Dominik Bindl/WireImage

Following his role as Mr. Napkin Head — oops, we mean Graham — in The Holiday, Law turned to the theater to play the title role in the West End production of Hamlet in 2009. The production eventually moved to Broadway, where Law earned a Tony nomination. Additionally, Law starred in a handful of Sherlock Holmes films with Robert Downey Jr. and gained critical acclaim for his role on HBO's The Young Pope. Most recently, he has appeared in blockbuster films including Captain Marvel and the Fantastic Beasts franchise, in which he plays a young Albus Dumbledore.

Cameron Diaz

The Holiday then and now
The Holiday then and now

Simon Mein/Sony/Kobal/Shutterstock; JB Lacroix/WireImage

After starring as Amanda in The Holiday, Diaz dove into a variety of movie genres including the psychological thriller The Box in 2009, the action-packed Knight and Day in 2010, and the comedy Bad Teacher in 2011. Following her roles in The Other Woman and the remake of Annie in 2014, Diaz retired from acting, and now focuses on parenthood and her natural wine business. She also released two health books The Body Book and The Longevity Book, with the latter becoming a New York Times bestseller.

Kate Winslet

The Holiday then and now
The Holiday then and now

Sony Pictures/Kobal/Shutterstock; Francis Specker/CBS via Getty

A few years after starring as Iris in The Holiday, Winslet reunited with Titanic costar Leonardo DiCaprio for 2008's Revolutionary Road, which earned her several acting awards including a Golden Globe for Best Actress. Winslet went on to star in various book-to-film adaptations including the Divergent franchise, The Dressmaker, and The Mountain Between Us. Most recently, Winslet gained critical acclaim for her role on HBO's miniseries Mare of Easttown, which earned her an Emmy for Outstanding Lead Actress in a Limited or Anthology Series or Movie.

Jack Black

The Holiday then and now
The Holiday then and now

Sony Pictures/Kobal/Shutterstock; Taylor Hill/FilmMagic

Following his role as Miles in The Holiday, Black did some voice acting with his starring role in the Kung Fu Panda franchise. He also appeared on a handful of shows like The Office and iCarly and released more music with his band Tenacious D. His most recent movie roles include Goosebumps, The House With a Clock in Its Walls, and the Jumanji sequels.

Rufus Sewell

The Holiday then and now
The Holiday then and now

Columbia Pictures; Taylor Hill/FilmMagic

After playing Winslet's on-screen ex, Jasper, in The Holiday, Sewell went on to star in The Tourist, Abraham Lincoln: Vampire Hunter, and Hercules. His most recent films include The Father with Anthony Hopkins and M. Night Shyamalan's thriller Old.

Shannyn Sossamon

The Holiday then and now
The Holiday then and now

Columbia Pictures; Paul Archuleta/Getty

Sossamon starred in a handful of indie films after playing Maggie in The Holiday, including Life Is Hot in Cracktown with Kerry Washington and The Day with Shawn Ashmore. Her most recent roles include the 2015 supernatural horror film Sinister 2 and Fox's Sleepy Hollow series.

Emma Pritchard

The Holiday then and now
The Holiday then and now

Emma Pritchard and Miffy Englefield Credit:

Since playing one of Law's on-screen daughters, Olivia, Pritchard has seemingly stopped acting. Her first and only acting credit on IMDb is The Holiday. Pritchard doesn't appear to be active on social media, but The Sun reports she's about 19 years old now.

Miffy Englefield

The Holiday then and now
The Holiday then and now

Columbia Pictures; Miffy Englefield/Instagram

After playing Law's daughter Sophie in The Holiday, Englefield had a handful of small roles on shows like The Whistleblowers and Casualty but hasn't had any acting credits since 2011. Since then, the 22-year-old has become a mom. In April 2020, Englefield announced the birth of her daughter Frances Rosanna Lee Englefield.

Eli Wallach

The Holiday then and now
The Holiday then and now

Moviestore/Shutterstock

Wallach already had a notable resume before starring as Arthur in The Holiday, and he continued acting well into his 90s with films like 2008's New York, I Love You and 2010's Wall Street: Money Never Sleeps. In June 2014, Wallach died of natural causes at age 98.