Sweethearts movie with Kiernan Shipka is Millennial Ode to John Hughes

If “Rebel Without a Cause” took teenagers on screen seriously for the first time since the 1950s, John Hughes helped revitalize them again as a full-fledged genre in the 1980s. The new film “Sweethearts” celebrates both moments in film history.

“Sweethearts,” whose title is a nod to the 50s lingo of high school sweethearts in an era where they go on, is the directorial debut of “Dollface” creator and “Freakier Friday” screenwriter Jordan Weiss. The filmmaker co-wrote the script with his real-life best friend Dan Brier; Weiss and Brier’s relationship also partially inspired the not-quite-rom-com about Jamie and Ben, two freshmen who make a pact to break up with their high school sweethearts over Thanksgiving break … and realize they might actually have feelings for each other instead.

It’s fitting that Kiernan Shipka, a breakout star of the ’50s series “Mad Men” who later went on to lead the ’80s aesthetic of “The Chilling Adventures of Sabrina,” was the first star of “Sweethearts.”

“She was always who I dreamed of playing Jamie … She’s such a great performer on screen, but off screen she’s really, really smart,” writer/director Weiss told IndieWire about working with Shipka. “She had such great things to say about how she was going to bring Jamie to life, and I just knew she was going to be such a great leader of a set. And as a first-time director, I just knew she was going to be such a reliable, great energy to have.”

But who could balance Shipka’s Jamie? According to Weiss, for whom the character Jamie is a kind of surrogate, the film “had to live and die by the chemistry between her and whoever played Ben.”

Enter: “Booksmart” alum Nico Hiraga.

“There was no decision to make when Nico walked out of the room. I think he got the part about four seconds after the door closed and left their chemistry reading because it was so obvious,” Weiss said. “( Dan and I) wrote this together. We were both executive producers on the film. We really knew the dynamic we were looking for. And the way Nico and Kieran are so different they such opposite personalities, but there was just this magic when they made each other laugh, even when they were just goofing off between reading the scenes. I was like, ‘That’s them, that’s Ben and Jamie.’

The cast is rounded out by “Severance” star Tramell Tillman, Joel Kim Booster, Ava Demary, Charlie Hall and Christine Taylor.

And while the film is semi-autobiographical for Weiss, she encouraged the cast to improvise on set, especially to avoid making the script seem too “millennial.”

“I’m a big fan of improv. I’m definitely a comedy girl through and through, and I originally come from TV. TV is very democratic, the best joke wins, so I really have no ego about it. And I love when my actors make me look funnier than I am coming up with amazing things on set,” Weiss said. “I really tried to encourage and create an environment on our set where the actors could play, for them to improvise.. .where our actors, especially the younger generation, closer to the age of the characters than Dan and I are as people in our 30s…We really wanted to make sure this felt authentic to young people”

But, she said, “We were also pretty conscious of trying to avoid too much modern slang or language, just because I think that can date things.”

She added that “Sweethearts,” like her “all-time favorite director” John Hughes, had to have a “sense of timelessness” like “Ferris Bueller.”

“I think we were really intentional with the way we styled their costumes and the music we chose and the kind of slang we tried to avoid to create that evergreen timelessness,” Weiss said. “But we definitely sat down all our cool Gen Z actors on day one and we were like, ‘If we’ve written a line in the script that makes us seem like cringe millennials, you’re obligated to say it and tell us and to work on it with us.’”

It was also important that Shipka infuse the character Jamie with her own “experiences and touchstones and personal style and way of speaking” so that Jamie “isn’t just about me anymore,” Weiss said.

Regarding the character’s backstory, Shipka said, “(Developing a character) is always important to me, and I was lucky that in the movie there’s actually a glimpse of why Jamie is the way she is, so I thought about that a lot. I thought a lot about our friendship and our relationship growing up, and honestly, just being on set with such amazing props made it very easy to feel the energy of this movie while it was in production there, no green screen. It was very convenient and we just had a good time.”

Weiss wanted to build a ’50s-inspired idyllic town to emphasize how much Jamie and Ben’s perspectives on where they grew up would have changed after just a few weeks away at college. Those are the kind of rose colored glasses.

“A lot of what this movie is about is when you leave your hometown and come back from the first time after being away with fresh eyes, and I think that’s an interesting, nerve-wracking kind of cardinal event to be a young adult and going back to your hometown for the first time after you don’t live there anymore,” Weiss said. “The first time you go back to your bedroom and it’s not your bedroom anymore. And I think some times that can feel like you’re stepping into a time capsule or like you’re stepping into the past, and so I thought it would be a really cool interpretation of that feeling to embrace a little bit of a retro feel in our production design and our costumes. We have a lot of 1950s, mid-century aesthetic touches; even the title ‘Sweethearts’ is a reference to the term high school sweethearts on like ‘Archie Comics’ and my grandparents and sock hops and ‘Grease’.”

Of course, there’s another Shipka connection: The actress helmed “The Chilling Adventures of Sabrina,” which was literally an “Archie” cartoon.

“Sweethearts” aren’t everything cute – it also captures the heightened emotions of being a teenager trying to navigate adult situations. Shipka pointed to a “blowout fight scene” with Hiraga that she “really loved” filming. However, Hiraga did not.

“It was hard to do,” Hiraga said. “You look at this angel (Shipka) and your voice gets louder. It kind of keeps you from being too excited. I didn’t like that.”

Still, Shipka explained that it was a real-life time crunch that led to how intense the on-screen drama was.

“There was a thunderstorm situation and we didn’t have that long to film it before the set had to shut down,” Shipka recalled of the scene, “and I love a time limit or some kind of pressure. It felt like very high stakes , and when we did, it ended up being so cathartic.”

It helped that Shipka also saw herself in Jamie.

“I’m in my 20s, I have lots of guy friends, and there’s always that energy, at least for me, with a lot of people,” Shipka said of the will-they-won’t-they story. “I’m always thinking about what if, even if it’s not meant to be.”

“Sweethearts” writer/director Weiss hopes the film can live up to the John Hughes legacy of teenage angst and love on screen.

“(Hughes’) movies were so successful … because he took teenagers seriously and he took their stories seriously, and I think we tried to do the same,” Weiss said, “even though sometimes one of the characters could be a little misguided or maybe realizing something that to an adult would seem obvious, it’s still really meaningful to them.”

Weiss to adapt Curtis Sittenfeld’s bestselling novel “Romantic Comedy” and also sold a rom-com pitch to New Line Cinema about the NFL playoffs. She also wrote the “Freaky Friday” sequel, “Freakier Friday,” from “Late Night” and “And Just Like That” director Nisha Ganatra. Shipka’s “The Last Showgirl” co-star Jamie Lee Curtis reprises her original role from the 2003 film alongside Lindsay Lohan, Chad Michael Murray and Mark Harmon.

For Weiss, “Sweethearts” is a through line for all her projects.

“The theme of my career so far, and the kind of stories I’m really interested in, are unconventional love stories,” Weiss said. “I think ‘Dollface’ was a love story between a girl and her female friends, and ‘Sweethearts’ is a love story about platonic love, and ‘Freakier Friday’ is a love story of mothers and daughters.”

“Sweethearts” premieres November 28 on Max.