Jude Law in ‘The Holiday’: The Casting That Almost Wasn’t

The Holiday, released in 2006, is one of the most underrated movies of the early aughts. This modern classic tells the tale of Iris, played by Kate Winslet, and Amanda, portrayed by Cameron Diaz. Both characters, struggling with love, make the decision to swap homes for the holidays.

Amanda, a Los Angeles native and typical California girl, finds herself in the quaint, English countryside, inhabiting Iris’s snug Surrey cottage, while Iris experiences life in Amanda’s opulent Los Angeles mansion.

Amanda’s LA mansion is a perfect depiction of her successful and ambitious character, while Iris’s charming Surrey cottage in England, paints a picture of her humble and introverted personality.

This story follows their individual journeys of self-discovery and serendipitous romance, with Jack Black and Jude Law complementing the duo as their respective love interests.

The film, directed and written by Nancy Meyers, was unexpectedly popular, eventually raking in over 200 million at the box office. However, the pivotal casting process reveals a little known backstory, involving two very well-known actors, up for the roles eventually secured by Jude Law and Jack Black.

The role of Iris’s brother, Graham, famously played by Law, almost went to Iron Man himself, Robert Downey Jr. Winslet reportedly voiced a certain apprehension concerning Downey Jr.’s ability to convincingly portray a British character, citing his British accent as being subpar.

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While Downey Jr. is an actor of formidable talent, as seen in his performances in films such as Less Than Zero and Sherlock Holmes, it’s challenging to picture anyone other than Law, playing Graham with such bravado and charm.

Jude Law "The Holiday" and Cameron Diaz.

In more interesting behind the scenes news, the role of Jack Black, the music composer Miles, who catches Iris’s attention, could have been played by Jimmy Fallon. Fallon confessed that his audition for The Holiday was his last.

He stated that acting alongside Downey Jr. was a remarkable experience that led him to deem Downey as one of the finest actors of his generation. However, it was Jack Black who ultimately seized the role, successfully playing on the character’s humor and sensitivity.

The film also boasts a cameo by the legendary Dustin Hoffman, and roles by Rufus Sewell and Shannyn Sossamon as Jasper and Lindsay respectively. Eli Wallach’s character, Arthur, is a screenwriter who symbolizes Hollywood’s forgotten heroes. He also gives a poignant speech at an awards ceremony, honoring him, on the fleeting nature of fame.

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In spite of the initial uncertainty surrounding casting, The Holiday attained substantial success. It maintains an audience score of 80% on Rotten Tomatoes, made significant box office earnings globally, and earned recognition on IMDb’s list of top romantic comedies.

Kate Winslet and Jack Black in "The Holiday".

The cult following for the film has sparked requests for a sequel, a topic frequently brought up on social media. While there is no official confirmation of a sequel, fans hope there is a possibility of revisiting the charming Surrey cottage and the LA mansion in the Hollywood Hills.

The performances of Law and Black were perfect and it’s clear that Meyers’ ultimate casting choices were the right ones. Whether it was the strength of the original script or the production team – the same team involved in Something’s Gotta Give and The Parent TrapThe Holiday is a fun romantic comedy, wrapped in love and humor, and subtly infused with the Christmas spirit. The Holiday is now streaming on Amazon Prime Video.

If you love a good Christmas Rom-Com, you may enjoy our article on When Harry Met Sally.