Kevin Costner and Jake Gyllenhaal Join Forces for Honeymoon with Harry at Amazon MGM

Hollywood has its fair share of projects that take years — sometimes decades — to finally make it to the screen. One of those long-awaited films is Honeymoon with Harry, a heartfelt dramedy that has been in development for over 20 years. After countless false starts, studio shifts, and near-misses, the movie has finally found its home with Amazon MGM. Even better, it has secured two powerhouse actors: Kevin Costner and Jake Gyllenhaal.

Directed by Glenn Ficarra and John Requa, with a screenplay by Dan Fogelman, the film is shaping up to be one of the most anticipated releases on Amazon MGM’s slate.

A Story Two Decades in the Making

Honeymoon with Harry first entered Hollywood’s radar back in 2004. The script was adapted from an unpublished novel by Bart Baker and immediately sparked interest across the industry. The film tells the emotionally charged story of a man (played by Jake Gyllenhaal) who loses his fiancée just two days before their wedding. Struggling to cope with his grief, he embarks on the planned honeymoon anyway — but not alone. He’s joined by his would-be father-in-law (played by Kevin Costner), leading to a complicated, funny, and deeply moving journey of healing and unexpected bonding.

The unusual premise — blending comedy, drama, and bittersweet human emotion — has kept Honeymoon with Harry alive in industry circles, even as multiple attempts to launch it stalled.

The Creative Team Behind the Project

The directorial duo Glenn Ficarra and John Requa are known for their ability to balance humor with heartfelt storytelling. Their work on Crazy, Stupid, Love proved they can handle a mix of comedy and drama with nuance, while their collaboration with Dan Fogelman on Hulu’s Paradise showcased their strength in character-driven narratives.

PASADENA, CALIFORNIA – JANUARY 09: (L-R) John Requa and Glenn Ficarra of Paramount+’s ‘Rabbit Hole’ pose for TV Guide Magazine during the 2023 Winter Television Critics Association Press Tour at The Langham Huntington, Pasadena on January 9, 2023 in Pasadena, California. (Photo by Maarten De Boer/Getty Images)

Fogelman, who wrote the screenplay, is best known as the creator of This Is Us and the writer behind Crazy, Stupid, Love. His track record of tugging at audience heartstrings makes him an ideal fit for this emotional story.

This powerful creative lineup gives Honeymoon with Harry an added boost of credibility — and raises expectations for its eventual release.

A Rocky Development Journey

The journey to get Honeymoon with Harry on screen has been anything but smooth. Over the years, the project has attracted A-list talent, but timing, script changes, and studio shifts repeatedly stalled its progress.

  • Early drafts: Paul Haggis, the Oscar-winning filmmaker behind Crash, once wrote a draft and was set to direct. At the time, Vince Vaughn and Jack Nicholson were circling the lead roles.
  • Jonathan Demme’s involvement: The acclaimed director of The Silence of the Lambs briefly considered the project with a script written by Jenny Lumet (Rachel Getting Married).
  • 2015 reboot: Fogelman came on board, and New Line eyed Bradley Cooper and Robert De Niro for the starring roles.
  • 2017 attempt: Director Nick Cassavetes was attached for yet another version.

Through it all, producer Mike Karz refused to give up. When rights lapsed and various versions fell apart, he continued pushing, eventually finding the right home at Amazon MGM.

Amazon MGM’s Role

Amazon MGM has been expanding its range of films, from romantic comedies to action blockbusters. Securing Honeymoon with Harry not only adds prestige to its lineup but also reunites the studio with producer Mike Karz, who previously delivered the rom-com Upgraded and action flick One Fast Move for the streamer.

The project also marks the producing debut of Jennifer Salke, the former head of Amazon MGM. Salke will produce the film under her new banner, Sullivan Street Productions, adding another layer of significance to the movie’s journey.

The Stars: Costner and Gyllenhaal

The casting of Kevin Costner and Jake Gyllenhaal is a dream pairing that instantly elevates the project.

  • Kevin Costner: An Oscar-winning legend, Costner has spent recent years focused on his ambitious Western saga Horizon: An American Saga. Though only two of the planned four parts have been made (with one released), the project has kept him in the spotlight. His return to a heartfelt dramedy like Honeymoon with Harry gives fans a chance to see a different side of him.
  • Jake Gyllenhaal: A versatile actor known for his roles in Nightcrawler, Prisoners, and Brokeback Mountain, Gyllenhaal is no stranger to emotionally complex roles. Recently, he starred in Amazon’s Road House remake, which became one of the platform’s biggest streaming hits, securing a sequel. He also earned critical acclaim for his role in Apple TV+’s Presumed Innocent, earning an Emmy nomination.

Together, the duo brings star power, acting chops, and credibility that should ensure audiences give Honeymoon with Harry the attention it deserves.

Why This Film Matters

At its core, Honeymoon with Harry is more than just another dramedy. It’s a story about grief, healing, and the unexpected bonds that can form through shared pain. With Costner portraying a grieving father and Gyllenhaal as a devastated fiancé, the emotional weight of the story is bound to resonate with audiences.

The film also represents persistence — not just within the story itself, but in its own long journey to the screen. After more than two decades of development hell, the project finally has the right mix of talent, timing, and support to bring it to life.

Conclusion

After years of near-misses, studio changes, and endless speculation, Honeymoon with Harry is finally a reality. With Amazon MGM backing the film, Glenn Ficarra and John Requa directing, Dan Fogelman scripting, and two powerhouse actors — Kevin Costner and Jake Gyllenhaal — leading the cast, this movie has all the ingredients of a modern classic.

More than just a film, it’s a story about second chances — both on and off-screen. For audiences, it promises laughter, tears, and the kind of heartfelt storytelling that sticks long after the credits roll. For Hollywood, it proves that some stories are simply too good to give up on.

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