‘Something From Tiffany’s’: How Inclusive Storytelling Drove the Casting and Adaptation of the Holiday Rom-Com

Hello Sunshine president of TV and film Lauren Neustadter takes TheWrap inside the making of the Prime Video feature

Kendrick Sampson and Leah Jeffries in "Something From Tiffany's" (2022)
Amazon Prime Video

Producer of “Something From Tiffany’s” Lauren Neustadter credits costars Kendrick Sampson (“Insecure”) and Zoey Deutch (“Not Okay,” “Set It Up”), as well as casting director Ronna Kress, with transforming the story of the film, adapted from Melissa Hill’s book that came out over a decade ago. 

“I read it when it was in galley [advanced, not finished format] and it’s a delightful book with an A+ movie premise. I immediately gravitated towards the premise of the book,” Neustadter told TheWrap in a recent interview. “I thought the characters were incredibly charming, but it wasn’t the kind of thing where there was a lot of specificity around the roles and the backgrounds of each of the characters. It was written in a bit of a different moment in time, and so we were imagining the script now, and we were imagining making the movie now. It was just something that I think we wanted to make sure that we were incredibly inclusive.” 

In addition to the casting of Sampson and Deutch as the interracial couple at its center, the film stars Shay Mitchell (“Pretty Little Liars”) and Ray Nicholson (“Licorice Pizza,” “Promising Young Women”). Rachel (Deutch) runs her own small bakery and restaurant business while remaining patient with her tattoo artist boyfriend Gary (Nicholson), who gets hit by a car when shopping for a vague gift for her from Tiffany and Company. Ethan (Sampson), a creative writing professor yearning to move back to New York City to take another shot at writing a novel, happens to be picking out an engagement ring for his girlfriend Vanessa (Mitchell) with the help of his daughter Daisy (Leah Jeffries). In a classic serendipitous switcheroo, Gary and Ethan unknowingly swap Tiffany and Co. jewelry bags after Ethan rushes to Gary’s aid outside the store. This later brings Ethan and Rachel together randomly at the hospital where the first sparks between them ignite.

“We were very clear that the premise is a little bit heightened, so the movie needs to be very grounded,” Neustadter said of the film’s tone. “The big movie moments and the bag swap is a heightened circumstance, and then everything that surrounds it has to feel real, it has to be real for these characters.”

Enter Rachel’s Gillini bakery, which she runs with her business partner and good friend Terri (Jojo T. Gibbs), whose comedic timing often steals the spotlight. Terri — whose partner Sophia (Javicia Leslie) softens Terri’s blunt edges — challenges Rachel over her relationship status with Gary and sharp analysis of his behavior and personality. 

Jojo T. Gibbs and Javicia Leslie in "Something From Tiffany's" (2022)
Amazon Prime Video

“This is one of those movies where there are people that are going to wind up together and there are people that are going to wind up not with the people that they started off with at the beginning of the movie, but no one’s a villain,” Neustadter said of the film’s twist on the traditional rom-com premise before adding, “Everyone deserves love.”

While the premise of the novel and its charming characters initially hooked Neustadter, the cast took the story to new dimensions of diversity and inclusivity, featuring nonwhite leads and a Black, lesbian couple. Deutch — whom Neustadter’s Hello Sunshine business partner Reese Witherspoon loved in “Set It Up” — was brought onboard around the same time as casting director Ronna Kress, who took it from there. 

“We knew and loved [Kendrick] from ‘Insecure.’ He blew us away in his audition. I remember he had actually just landed from a flight and he got on a Zoom with us and he was just so lovely and so charming,” Neustadter recalls. “He brought so much to the role instantly, but he also was very clear with us that if we cast him, he would really want to come in and talk through the script with us.”

Sampson brought on LA-based Black Latina creative consultant Zion Estrada, who currently serves as Director of Programs at BLD PWR (BUILD POWER), a nonprofit organization that calls on athletes and entertainers to bring about social change with their respective platforms, to dig into Tamara Chestna’s script with Neustadter. 

“There were lots of incredibly thoughtful conversations about Ethan and the women who he was in relationships with and what story we were telling there that mattered deeply to Kendrick and also to us.” Neustadter reiterated. “The conversations were really enlightening and thought-provoking, and I think they ultimately really informed much of the film and certainly much of the relationship that Ethan has with his daughter Daisy, and the relationships that Ethan has with characters in the movie.”

Sampson’s character had been married before, but he and his daughter are now navigating life after the death of his first wife. The actor pushed hard for a scene in which his single dad character carefully does Daisy’s hair, a poignant moment for any father, let alone a Black one caring for Black hair. 

Leah Jeffries and Zoey Deutch in “Something From Tiffany’s” (2022) (Amazon Prime Video)

“He really was thinking about his character, and he was thinking about what would his life be like if he was a single dad? What are the things that he would have learned to do and what are the responsibilities that he would have taken on?” Neustadter said. “That was something that we really talked about, and that was an idea that he had that we all absolutely loved.”

Deutch, Neustadter and director Daryl Wein combined forces to bring Jewish touches to the Christmas season setting of the story and film as well, inspired by the fact that Deutch is Jewish.

“We were all sort of loving the fact that we were all Jewish people who really love Christmas romance and holiday romance, and they really dug in to the script. They were like, you’re Jewish, let’s have Rachel be Jewish,” Neustadter said. “And so you notice he’s wearing her Zabar’s shirt, and we say Happy Hanukkah. It comes down to making it honest. I love that this movie has a lead female character who is all of these great things, and is also proud to be Jewish.”

Dimensionality, diversity and inclusivity frame many a Hello Sunshine production, and will continue to do so in the future with upcoming adaptations like “Daisy Jones & the Six.”

“Making sure that the stories that we’re telling are dimensional is a part of what we always strive to do [at Hello Sunshine]. We always strive to really be thoughtful about each character. What is their lived experience, where are they coming from?” Neustadter said. “In television, we have the privilege of having writers rooms that are incredibly representative. If you look back to ‘Little Fires Everywhere’ and that room, we were so careful about making sure that each point of view was represented and not just by one individual,” Neustadter said. “It’s something that we were very, very intentional aboutaround ‘Daisy Jones & the Six,’ which is a show that we have that’s going to be coming out next spring, we just announced.”

Not to mention the bright and joyful feelings that spring to mind when you read the production company’s name. Neustadter credits the cast that came together to pull of this sparkling, heartwarming and cheerful Christmas rom-com.

“If you think about the holidays, I think we are living in a moment where it’s very easy to be cynical. I love that this movie is not cynical. It’s a movie that is romantic, that is hopeful, that is optimistic. I think at the holidays and always we could use a little romance, a little hope and a little optimism. I think that’s something that this movie delivers in spades.”