First Look: Honeymoon with Harry Finally Begins Filming After 20 Years

• Kevin Costner and Jake Gyllenhaal will star in Honeymoon with Harry after 20 years in development.
• The film follows a man who takes his late fiancée’s father on their planned honeymoon.
• Glenn Ficarra and John Requa direct from Dan Fogelman’s script.
• Jennifer Salke produces her first project since leaving Amazon MGM.

For two decades, Hollywood has chased the bittersweet love story of Honeymoon with Harry—a project that survived rewrites, recasts, and studio shifts. Now, the wait is over.

Amazon MGM Studios has officially set Kevin Costner and Jake Gyllenhaal to star in the dramedy, marking the end of a 20-year journey to bring Bart Baker’s novel to the screen.

Directed by Glenn Ficarra and John Requa (Cr@zy, St#pid, Love), the film promises a poignant yet humorous take on grief, family, and unexpected bonds.

A Two-Decade Journey to the Screen

The film’s path began in 2004 when producer Mike Karz first secured the rights at New Line Cinema. Over the years, A-list talent circled the project, including Vince Vaughn, Jack Nicholson, Bradley Cooper, and Robert De Niro. At one point, Oscar winner Paul Haggis (Crash) was attached to direct, while Rachel Getting Married scribe Jenny Lumet penned a draft.

“It’s been a courtship lasting over 20 years, but Honeymoon with Harry is one love story that Hollywood can’t quit,” noted The Hollywood Reporter

Despite setbacks, Karz never gave up. When rights lapsed, he championed Dan Fogelman’s (This Is Us) script, which ultimately landed at Amazon MGM.

The Story Behind the Film

Gyllenhaal plays a grieving man who, after his fiancée’s sudden death, embarks on her planned honeymoon—with her father Kevin Costner as his unlikely companion. The premise blends heartbreak with humor, a tone Ficarra and Requa mastered in Cr@zy, St#pid, Love.

“The film follows a man (Gyllenhaal) as he decides to go on a honeymoon with his would-be father-in-law (Costner) after his fiancée dies two days before their wedding,” Deadline reported

Jennifer Salke, former Amazon MGM chief, joins as a producer, reuniting with Fogelman after their This Is Us success.

Why This Casting Works

Costner and Gyllenhaal bring gravitas and emotional depth. The Yellowstone star’s recent work in Horizon showcases his ability to balance ruggedness with vulnerability, while Gyllenhaal’s Emmy-nominated turn in Presumed Innocent proves his dramatic range.

“Gyllenhaal is an Amazon favorite thanks to starring in last year’s remake of Road House, which became one of the streamer’s biggest hits ever,” noted The Wrap

Their dynamic—a grieving son-in-law and a stoic patriarch—could mirror the chemistry of Sideways meets The Descendants.

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Last Updated on August 18, 2025 by 247 News Around The World