Festive rom-com “The Holiday” is a modern Christmas classic. The 2006 movie, which released 19 years ago on December 8, is now a staple watch for many at this time of year.
It starred Cameron Diaz and Kate Winslet as two lovelorn women from the United States and United Kingdom, respectively, who arrange to swap homes to escape their personal heartbreak over the Christmas season. Jude Law and Jack Black co-star as the men the ladies meet and fall for when they cross the Atlantic.
But what do Diaz, Winslet, Law, Black, and their supporting cast look like now compared to what they looked like back then? Let’s take a look…
Jude Law (Graham Simpkins)
Jude Law played Graham Simpkins in “The Holiday.” Graham is a widower, single father, and book editor who meets Amanda Woods when she temporarily moves into his sister Iris’ home for the festive period. Law was just shy of turning 34 when the movie released.
He had been acting for over 15 years at the time, with most of his credits coming in movies. His notable recent credits included 2004’s romantic comedy-drama “Alfie” and epic biographical drama “The Aviator,” and the political drama “All the King’s Men” and romantic crime drama “Breaking & Entering” earlier in 2006. (per IMDb).
GettyLaw is now 52 and has starred in some huge movies since “The Holiday,” including 2009’s period mystery action move “Sherlock Holmes” and the “Fantastic Beasts” movies as a young Albus Dumbledore. Most recently, he appeared in the 2024 crime drama “The Order” and historical survival thriller “Eden” in the same year.
GettyCameron Diaz (Amanda Woods)
Cameron Diaz was 34 when “The Holiday” hit theaters. She played successful production company owner Amanda Woods, who temporarily moves to Surrey, England from Los Angeles, California when she swaps homes with Iris Simpkins.
Diaz had enjoyed a hugely successful movie career at that point, with her most recent credits including voicing Princess Fiona in the “Shrek” franchise, 2002’s epic historical drama “Gangs of New York” and sci-fi action flick “Minority Report,” and 2005’s romantic comedy-drama “In Her Shoes” (per IMDb).
GettyIn 2018, Diaz announced that she had retired from acting, with her most recent movie roles before that coming in 2014’s rom-com “The Other Woman,” sex comedy “Sex Tape,” and musical comedy-drama “Annie.” However, in 2025, she came out of retirement to appear in the Netflix action comedy “Back in Action.” In 2027, she will reprise her role as Princess Fiona in “Shrek 5.” Diaz is now 53.
GettyKate Winslet (Iris Simpkins)
Kate Winslet played society columnist Iris Simpkins in “The Holiday.” She swaps homes with Amanda Woods for Christmas, moving from Surrey, England to Los Angeles, California. Winslet was 33 when the movie released.
Winslet was a huge star at the time, having made her name with movies like 1997’s epic romantic disaster movie “Titanic.” Her most recent film credits prior to “The Holiday,” all in 2006, were documentary movie “Deep Sea 3D,” animated adventure comedy “Flushed Away,” political drama “All the King’s Men,” and satirical melodrama “Little Children” (per IMDb).
GettyNow 50, Winslet’s career has gone from strength to strength, which included winning the Academy Award for Best Actress for her brilliant performance in 2008’s romantic drama “The Reader.”
Her most recent roles have come in 2025, in the family Christmas drama “Goodbye June” and the epic sci-fi sequel “Avatar: Fire and Ash,” which releases on December 19.
GettyJack Black (Miles Dumont)
GettyActor, comedian, and musician Jack Black played Miles Dumont, a Hollywood film composer working with Amanda Woods who becomes romantically involved with Iris Simpkins when she spends Christmas in California. Black was 37 when “The Holiday” released.
He had been acting for over 20 years and had movie credits dating back to 1992. His most recent credits prior to “The Holiday” were the sports comedy “Nacho Libre” and the musical fantasy comedy “Tenacious D in The Pick of Destiny,” both earlier in 2006 (per IMDb).
GettyBlack is now 56 and still a huge star. Some of his most recent movie credits include 2024’s animated martial arts comedy sequel “Kung Fu Panda 4,” 2024’s sci-fi comedy “Borderlands,” and 2025’s hugely successful fantasy adventure “A Minecraft Movie.”
Eli Wallach (Arthur Abbot)
Eli Wallach had just turned 91 when “The Holiday” hit theaters. In the film, he played Arthur Abbott, a famous screenwriter and Amanda Woods’ neighbor who befriends Iris Simpkins when she temporarily moves into Amanda’s home for the festive period.
Wallach had enjoyed an acting career spanning over half a century at that point. He’d appeared in iconic films like the Westerns “The Magnificent Seven” and “The Good, the Bad and the Ugly” in 1960 and 1966, respectively. His most recent credit before “The Holiday” was the 2006 comedy-drama “The Hoax” (per IMDb).
GettyWallach sadly passed away from natural causes at the grand age of 98 on June 24, 2014. He acted in several more movies after “The Holiday,” with his final feature role being in 2010’s drama movie “Wall Street: Money Never Sleeps.”
May the great Eli Wallach rest in eternal peace.
GettyRufus Sewell (Jasper Bloom)
Rufus Sewell played Jasper Bloom, the emotionally-needy ex-boyfriend of Iris Simpkins, in “The Holiday.” He was 39 when the movie came out.
At that time, he had been acting on screen for around 15 years. He had appeared in four movies before “The Holiday” in 2006 alone. They were the epic romantic drama “Tristan and Isolde,” the romantic mystery film “The Illusionist,” the anthology movie “Paris, je t’aime,” and the biological drama “Amazing Grace” (per IMDb).
GettySewell is now 58 and has continued to act sporadically in movies since 2006. His most recent credits came in 2024. They were the comedy-drama “The Uninvited” and the biographical drama “Scoop.”
GettyEdward Burns (Ethan)
Edward Burns played Ethan, Amanda Woods’ unfaithful composer boyfriend whom she breaks up with at the start of “The Holiday.” Burns was 38 when it hit theaters.
At that point, he had only been acting for around a decade and the biggest movie he had appeared in was undoubtedly 1998’s epic war flick “Saving Private Ryan.” His most recent film credit prior to “The Holiday” was 2006’s comedy “The Groomsmen” (per IMDb).
GettyBurns is now 57 and continues to act, though far from prolifically — although he also directs, produces, and writes. His most recent acting credits include roles in 2024’s family drama “Millers in Marriage” and 2025’s comedy-drama “The Family McMullen.”
GettyThis festive season, when compiling your holiday watchlist, make sure you include “The Holiday.” It has everything from laughs and festive cheer to charm and sentimentality.
