Moviestore/Shutterstock

1. Director Nancy Meyers wrote her starring ladies Iris and Amanda with Kate Winslet and Cameron Diaz successful mind. 

"You know, I deliberation a screenwriter would prevarication to you if they said, 'I don't deliberation astir anybody erstwhile I americium writing,'" the famed scribe told ComingSoon.Net. "I can't ideate it, you cognize idiosyncratic has got to accidental it and bash it. It's earthy to commencement fantasizing astir who is going to beryllium successful it."

2. To beryllium fair, casting Winslet was beauteous overmuch a no-brainer. "If you're penning a 30-year-old pistillate successful England you evidently deliberation of Kate Winslet," Meyers explained. "She's conscionable 1 of the large actresses."

3. While Winslet was the inspiration for Iris, the Titanic prima was convinced she was going to beryllium fired from the movie. 

"I've ne'er done a romanticist drama oregon thing that is labelled arsenic that before," Winslet explained to About.com successful 2006. "I was truthful excited to bash thing caller and besides tense you know? The interest of, 'Can I beryllium funny?' It's a unspeakable happening to beryllium acrophobic about. And Jude [Law] and I would talk connected the telephone a batch earlier we started shooting. 'Oh my god, they're going to occurrence us! They're going to recast. What if we don't marque them laugh?' You know, precise tense astir the full thing."

Moviestore/Shutterstock

4. When it came to her California-based movie trailer exertion who ne'er cries, Diaz was an evident choice for Meyers.

"Cameron is simply a large comedienne and I thought astir this earlier I formed her and erstwhile I formed her she continued to thrill maine successful that area," Meyers said. "It's truly hard I deliberation to beryllium that cute and sexy and that comic and that benignant of girl-friendly. I americium truly lone funny with women successful my movies that are girl-friendly, I'm astir apt ne'er going to enactment with those girls that lone the guys similar due to the fact that I conscionable don't get them. So Cameron's truly a girl's miss and boys adore her obviously. She seemed perfectly the close prime for a California girl."

5. Though Law made millions of movie-goers swoon arsenic azygous dada Graham, helium wasn't what Meyers' initially had successful caput for the part.

"Jude's quality evolved much during the penning than the others," she admitted. "I benignant of enactment him done immoderate twists and turns that you don't expect. Then, erstwhile I was done, of people you deliberation of Jude Law. He's truthful handsome and he's truly specified a terrific actor, but I wasn't instantly definite that helium was going to acceptable into the genre and bash this benignant of work. So I met with him and we went done the publication unneurotic and helium conscionable got it. You know, helium conscionable hasn't had a accidental to bash it before."

Moviestore/Shutterstock

6. For Miles, Iris' emotion interest, Meyers wrote the relation for Jack Black aft seeing him successful School of Rock, explaining to ComingSoon.net, "I conscionable adored him, I thought helium popped disconnected the screen. He spoke to maine arsenic an assemblage member."

"When I was reasoning of this movie I thought helium was idiosyncratic I would similar to constitute a portion for and I'm alert he's not Clark Gable, he's not gangly acheronian and handsome, but he's adorable, he's lovable," she continued. "It's my mode of saying this is the close benignant of guy, this is what astir guys look similar if they're lucky, he's truthful adorable, and wherefore not? Everybody has a bosom and deserves to autumn successful emotion and helium should get a large girl. So I fixed him up with Kate Winslet."

7. And it was being partnered with Winslet that yet got an unsure Black to motion on, with Meyers adjacent trying to woo him implicit a pasta dinner. 

"Kate was unthinkable arsenic I anticipated," Black told Coming Soon successful 2006. "It was a immense crushed wherefore I wanted to bash the movie. I was specified a large instrumentality of hers, I conscionable emotion her enactment and her acting."

Moviestore/Shutterstock

8. Miles and Iris' boob graze infinitesimal wasn't successful the archetypal publication and was inspired by a existent brushwood betwixt Black and Meyers.

"One time connected the acceptable helium bumped into maine and said, 'Oh, atrocious astir the boob graze,'" Meyers told Coming Soon. "I conscionable laughed truthful hard due to the fact that men bump into women each the clip similar that and enactment similar they didn't bash it, but helium instantly said atrocious astir the boob graze truthful I wrote it into the adjacent country helium did."

9. Winslet and Rufus Sewell, a.k.a. Iris' precise atrocious ex-boyfriend Jasper, really dated IRL successful the aboriginal 1990s for a fewer months. But things weren't awkward connected set.

"It was wholly fine," Winslet told the Irish Examiner. "I hadn't seen him for a precise agelong clip but we'd remained friends. It was truly not a large deal. I was thrilled helium got the part."

Moviestore/Shutterstock

10. Sure, Amanda's Los Angeles location is gorgeous, but Iris' cute state cottage was the existent swoonworthy determination among the crew. After initially uncovering a charming home, the producers decided to physique their ain truthful they could beryllium person to London.

Calling Meyers "a perfectionist," Law explained during a November 2024 appearance connected BBC Radio 2’s The Zoe Ball Breakfast Show, “She toured the full country and didn’t rather find the cocoa container cottage she was looking for. So she conscionable hired a tract and drew it and had idiosyncratic physique it.”

The accumulation squad created Rosehill Cottage successful lone 2 weeks, with Meyers saying successful a DVD feature, "We built that partition and we enactment successful those trees. It truly was conscionable an bare field. It was a existent tourer attraction portion it was there."

Unfortunately, the gathering was torn down aft filming and each of the interior scenes were done connected a dependable signifier successful Culver City, Calif. Thus, Meyers instructed her cinematographer Dean Cundey not to instrumentality immoderate wide shots wrong the cottage truthful it would consciousness tiny and cozy.

11. One of the film's astir iconic moments is Law's Mr. Napkinhead performance, with a bulk of the country being improvised, according to Miffy Englefield, who bushed retired implicit 2,500 actresses to play Graham's daughter, Sophie. Englefield revealed to Vulture that Law came up with the enactment astir smoking being atrocious for you, portion Englefield genuinely told Diaz that the spot was "so funny, you'll autumn disconnected your chair." 

Moviestore/Shutterstock

12. Lindsay Lohan and James Franco marque unexpected cameos arsenic the stars of a movie Amanda's institution is cutting the trailer for. 

"I cognize Lindsay due to the fact that I directed The Parent Trap and I told her she owes maine everything truthful I made her bash it," Meyers told ComingSoon.Net of the fake film's origin. "I called her and said, 'You person to bash this for me,' but she was saccharine astir it, she was wholly there."

As for Franco, helium and Meyers had met astatine a fewer meal parties done communal friends. "So, I knew him a small spot and I asked him if helium would bash it," she added, "and it turned retired Lindsay and James knew each different and it was truly fun."

13. During a 2006 quality connected The Tonight Show With Jay Leno, Dustin Hoffman revealed his cameo during the Blockbuster country was unplanned. The Oscar victor happened to beryllium driving by that store and stopped to spot what was filming. After talking to Meyers for a bit, she said, "'Wait, I got an idea,'" Hoffman explained. "So she enactment maine successful the movie. And similar a fool, I didn't negotiate."

Moviestore/Shutterstock

14. Amanda's large dash backmost to the cottage to instrumentality to Graham wasn't successful the script.

"Literally, I was truthful acceptable by the extremity of that week," Diaz told Vulture past year. "I ran astir apt 7 miles a time successful those heels. Through mud and hills. It was truthful hilarious. I was literally, like, I'm not adjacent complaining close present due to the fact that my occupation is to run, and I'm good with that. But I'm sweating!"

15. An icon successful the rom-com genre, The Holiday proved to beryllium "really hard" for Meyers to constitute aft 2003's Something's Gotta Give due to the fact that of the storylines.

"I truly wanted to constitute a broader canvas, but not a broader taxable by penning aggregate characters and aggregate stories and it was really amusive trying to weave them together," Meyers admitted. "The lone conscious happening I did was to not person each miss conscionable 1 person. So, connected Kate's broadside of the movie she befriends Eli and that narration and helps her and guides her. I conscionable thought it would beryllium amended for the assemblage not to person 2 girls who instantly conscionable guys and autumn successful emotion and person that benignant of parallel situation, but it was truly amusive to constitute an ensemble movie."