Kevin Costner and Jake Gyllenhaal team up as 'Honeymoon with Harry' sets filming date after 20 years

Under development since 2004, 'Honeymoon with Harry' has eyed numerous actors, including Bradley Cooper and Robert De Niro
Kevin Costner in a still from ‘Yellowstone’; Jake Gyllenhaal in a still from ‘Presumed Innocent’ (Cover Image Source: (L) Yellowstone | Photo by Emerson Miller; (R) Apple TV Press | Presumed Innocent)
Kevin Costner in a still from ‘Yellowstone’; Jake Gyllenhaal in a still from ‘Presumed Innocent’ (Cover Image Source: (L) Yellowstone | Photo by Emerson Miller; (R) Apple TV Press | Presumed Innocent)

'Honeymoon with Harry,' which has been in development for over 20 years, finally set a production date with Kevin Costner and Jake Gyllenhaal. The movie, a passion project for producer Mike Karz, was originally set up in 2004. The movie even had a draft script, penned by 'Crash' writer Paul Haggis, ready, as per The Hollywood Reporter. Since then, 'Honeymoon with Harry' has eyed numerous actors, including Bradley Cooper and Robert De Niro. Now, 21 years later, Costner and Gyllenhaal will be teaming up for their first movie together to bring Karz's vision to life. 

Kevin Costner as John Dutton in 'Yellowstone' (Facebook/@Kevin Costner & Modern West)
A still of Kevin Costner as John Dutton from 'Yellowstone' (Image Source: Facebook | @kevincostner&modernwest)

'Honeymoon With Harry' was officially confirmed in August 2025, with Dan Fogelman set to write the script. With the cast finalised and pre-production nearly complete, the makers have now announced the filming schedule. At CCXP in Brazil, Fogelman revealed that filming is set to begin in March 2026. Speaking about casting Costner and Gyllenhaal, he told Collider in an exclusive interview, "There had been 18 billion iterations of different cast members playing the two main characters," adding, "For us, it's Jake [Gyllenhaal] and Kevin Costner and my guys, John [Requa] and Glenn [Ficarra]...They've been my partners for a lot of things, and they're going to go and direct it with those guys. We're gonna start shooting in March."

Saying he had always wanted to make a movie of a self-published book by "wonderful writer" Bart Braker, Fogelman noted Honeymoon With Harry's long journey through development. "I don't believe anything's officially going until your cameras are rolling, and the movie stars are on set. We're as close as you get. It's as close as this one's gotten before. We're making plans, so it's pretty close," he told Collider. Notably, Amazon MGM and Karz's Gulfstream Pictures have teamed up for the movie. 

When it was first conceptualized, Karz's 'Honeymoon with Harry' was signed up at New Line Cinema. At the time, Haggis had written the draft with Vince Vaughn and Jack Nicholson considered for roles, as per CBR. Fogelman has been attached to 'Honeymoon with Harry' since 2015, originally with Bradley Cooper and Robert De Niro considered as leads. The movie, based on Braker's book, centers on two grieving men who must set aside their mutual hatred to cope with the loss of the woman they both loved.

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