Nearly a decade after his ambitious first feature (which then became three features) and filmmaker Ned Benson is finally back on the big (and small) screen. His second film, “The Greatest Hits,” arrives ten years after his directorial debut, the 2014 breakout feature “The Disappearance of Eleanor Rigby.” And this time, Benson is letting his protagonist have a happily ever after … kind of.

During a recent interview, Benson told IndieWire that, in a similar twist to his “Eleanor Rigby” process, the script for “The Greatest Hits” was one he had been tinkering with for years, starting in 2008. Unlike “Eleanor Rigby,” which was eventually split into a “Him”/”Her”/”Them” mini trilogy, “The Greatest Hits” firmly centers on sole lead Harriet (Lucy Boynton), whose heartbreak leads to a music-induced time travel back to her past relationship with her late lover (David Corenswet) prior to his death.

In her present, Harriet grapples with crippling anxiety, grief, and the possibility of opening her heart up again to a new crush (Justin H. Min). Should Harriet change her past to stay away from her ill-fated ex and never feel that pain, or was it all worth it to make her into the woman she is today? As Harriet is caught between two men, two timelines, and two potential heartbreaks, Benson (who wrote and directed the film, in addition to producing it) still calls the film his version of a “cotton candy” rom-com, despite its weighty existential debate.

“I love relationships,” Benson told IndieWire. “I’m a sucker for a cotton candy romance and I think, in this case, I wanted to make my own version of a cotton candy romance. ‘Eleanor Rigby’ is obviously a much more intense movie, but they’re both dealing with grief and loss and letting go, which are themes in this movie too. But I think in that movie, letting go is the overall theme, but this movie is also learning how to live again too.”

Justin H. Min and Lucy Boynton in THE GREATEST HITS. Photo by  Merie Weismiller Wallace, Courtesy of Searchlight Pictures. © 2024 Searchlight Pictures All Rights Reserved.
Justin H. Min and Lucy Boynton in ‘The Greatest Hits’Merie Weismiller Wallace/Courtesy of Searchlight Pictures

Benson recalled the “really long journey” behind getting “The Greatest Hits” greenlit. “I kind of came up with the idea in 2008 after reading this book by Oliver Sacks called ‘Musicophilia,’ which is just about music in the brain, things like musical hallucinations, aphasia, and I’m just such a music freak,” Benson said, citing Harriet’s ability to travel back in time when a song she has a memory with plays. “I’m obsessed with music and what it does to me and how it sort of forms nostalgia. So many songs and so much music just transports me back to the past and sort of helps remind me to live my life too, so I wanted to write a movie about that.”

Benson said that he eventually put away his early drafts to focus on “Eleanor Rigby” and other projects. “I tried to make two other films,” he said. “One we just couldn’t get the financing for and another, I really loved it but I think what the people I was working on it with realized was I was not the right person to direct that movie. And then the pandemic hit and my manager was like, ‘Why don’t we pull this off the shelf and let’s look at it?’”

He continued, “During COVID, music really was this salve. Between my friends, my wife, it really helped us through. It was quite an isolating time for everybody and I revisited the script through that lens. I wanted to make a love letter to Los Angeles, got a draft out, and when I sent it out, people bit, and I got to make another movie. Sometimes it’s not you who decides to make the movie you want to make; it’s what the business decides.”

The casting process led to script changes, with Benson even rewriting dialogue daily. While the original script included specific needle drops tied to Benson’s own music taste (“very upbeat, dance-y, positive, much more disco”) circa 2020, Benson wanted the story to come to life with the actors, especially Boynton.

Lucy Boynton and David Corenswet in THE GREATEST HITS. Photo by  Merie Weismiller Wallace, Courtesy of Searchlight Pictures. © 2024 Searchlight Pictures All Rights Reserved.
Lucy Boynton and David Corenswet in ‘The Greatest Hits’Merie Weismiller Wallace

“We had a meeting and she walked into the coffee shop and it was like, ‘Oh, yeah, this is Harriet,’” Benson said. “She’s an extraordinary actor in everything that she does, and she’s also just a lovely human being. It was a very easy, exciting process. She grilled me on the script, asked me questions about ‘How am I going to do this, how am I going to do that?’”

Those questions became part of the rehearsal process, with Benson “100 percent” opening up the script to any changes the cast saw fit. Benson and “Eleanor Rigby” star Jessica Chastain did the same thing during that production, leading to the three-part perspectives for that feature.

“I’m always kind of rewriting. I’m never really too precious on the script,” Benson said. “I think it’s more about finding the scene together. We did a rehearsal process where we worked through the script together and just saw what dialogue was working and what didn’t and what felt right. We’re playing with themes and ideas that seem ridiculous like time travel, but just making sure that things felt organic with each of them. We were listening to a lot of playlists together. That was leading up to it in pre-production, and then on the day we rehearse, we were finding the scene and rewriting the scene as we do it too. That’s a big part of my process.”

So would Benson ever consider doing a “The Greatest Hits” B-side with a different perspective other than Harriet’s? “Not at the moment, but never say never,” Benson said. “I definitely love perspective as I tried with my first film. We’re talking also about a musical version of this movie. I think we’ll see how it goes. I think there’s a lot of fun characters in it and you only have so much time with each character and in this case, I was sort of using Harriet as the lens for our story. Would I love to fill out all those other characters and discover them more? Of course.”

And despite the tweaks to the script, the ending always stayed the same, with Benson knowing exactly what he wanted “The Greatest Hits” to say.

Lucy Boynton in THE GREATEST HITS. Photo by Merie Weismiller Wallace, Courtesy of Searchlight Pictures. © 2024 Searchlight Pictures All Rights Reserved.
Lucy Boynton in ‘The Greatest Hits’Merie Weismiller Wallace

“I think as people we have this capacity to love multiple people at once in our hearts, and that no matter what our experiences are, I think we carry those relationships and those feelings with us however we want it to happen to them,” Benson said. “In this specific case, I really wanted this story to end on Harriet’s journey. It’s really about Harriet figuring out how to live her life again so that she has the ability to be in a new relationship, whatever that is. There’s this kind of mutual sacrifice between these people, which I think is all necessary for each of them, to not only move on to something that’s right for them but really that’s actually the healthiest version of love.”

But this isn’t actually the end of “The Greatest Hits,” nor Benson’s passion for telling complex romantic stories that have existential ties. It’s just a matter of funding for Benson’s future projects.

“Again, like what I talked about with this movie, what can you get made? There’s a ton of movies I want to make, but it’s whether you can get them made, if you can find the actor who believes in it, the financing to believe in it, etcetera, etcetera,” Benson said. “I think sometimes it’s just doing your best to make these things and seeing what happens. There are a few things I’m really excited about right now. We’ll see if they come together. If you had asked me 10 years ago what my next movie would be like, I wouldn’t have expected it to be this, but here we are. I wouldn’t change the experience.”

“The Greatest Hits” is now streaming on Hulu.

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