
When you hear that Kevin Costner and Jake Gyllenhaal are teaming up for a movie, you’d be forgiven for assuming it could be an addition to some of the best western movies or a tense political thriller. Costner's most recent work involved him playing cowboys in Yellowstone (available with a Peacock subscription) and his sprawling epic Horizon: An American Saga, while Gyllenhaal has built a career with some of his best movies being prestige dramas and intense genre pieces ranging from Nightcrawler to Prisoners. That’s why their latest project together is such a curveball.
Costner and Gyllenhaal have officially signed on to star in Honeymoon With Harry, an upcoming book-to-screen adaptation of a Bart Baker novel produced by Amazon MGM Studios, according to Deadline. The studio announced the film on Monday, with Glenn Ficarra and John Requa (Crazy, Stupid, Love; Focus) directing from a script penned by Dan Fogelman, the writer-producer best known for This Is Us and Crazy, Stupid, Love.

The story is said to follow a man (Gyllenhaal) who finds himself reeling when his fiancée tragically dies just two days before their wedding. In an unexpected turn, he decides to go on their trip anyway, and he's joined by his late bride's grieving father (Costner).
The unlikely pairing sets the stage for a mix of heartbreak, tension, and humor, as two men bound by tragedy find themselves navigating an unthinkable situation together. It’s an intimate premise that leans into character-driven storytelling, which is a noticeable shift from the blockbuster spectacle we’ve come to expect from both stars.
The film is also notable for its producing team. Alongside Fogelman and Mike Karz of Gulfstream Pictures, the project will mark the producing debut of Jennifer Salke under her new Sullivan Street Productions banner. Salke recently stepped down as head of Amazon MGM Studios, and this marks her first collaboration with the company since her exit. She reunites here with Fogelman, whose This Is Us she famously championed during her time as President of NBC Entertainment.

For Amazon MGM, the project also continues a creative partnership with Gulfstream Pictures, following recent collaborations on Upgraded, a romantic comedy starring Camila Mendes, and One Fast Move, a racing drama featuring KJ Apa and Eric Dane. Honeymoon With Harry has been floating in Hollywood circles for years, originally set up at New Line during Karz’s tenure there, before finally finding its footing at Amazon.
The casting comes at a busy time for both actors.
The Zodiac star is fresh off awards recognition for Apple TV+'s Presumed Innocent, which he also executive-produced. The courtroom drama became the streamer’s most-watched series to date and is already set for a second season. He also has two high-profile films on the horizon: M. Night Shyamalan’s next thriller, Remain, and Maggie Gyllenhaal’s The Bride! for Warner Bros.
Meanwhile, Costner continues to expand his career both in front of and behind the camera. In addition to his multi-part Horizon saga, he’s producing The Gray House, a Civil War spy drama limited series through his company Territory Pictures.
With Honeymoon With Harry, both of the A-list actors are heading into territory we don’t usually see them in, and that’s exactly what makes it so exciting. Instead of the big action pieces or sweeping epics they’re known for, this one’s shaping up to be a smaller, more personal story. Honestly, just the idea of watching these two share the screen in something this heartfelt is enough to put it high on my must-watch list.