Amblin Entertainment, founded by Steven Spielberg, bought the film rights to Robert James Waller's novel for just $25,000 in late 1991, before the book was even published; it went on to sell 9.5 million copies worldwide.

The project went through multiple directors and screenwriters before Eastwood took over: Spielberg first hired Sydney Pollack, who had Kurt Luedtke draft a version before dropping out, then Ronald Bass was brought in with unsatisfying results, and Bruce Beresford (with writer Alfred Uhry) was also attached before leaving when everyone preferred Richard LaGravenese's script.

Steven Spielberg enjoyed working on the script with Eastwood and LaGravenese so much that he considered directing Bridges himself as his next film after Schindler's List, before ultimately stepping back and letting Eastwood direct.

Eastwood and Spielberg rewrote LaGravenese's script together and added the framing device of Francesca's adult children discovering and reading her diaries after her death, which was not part of the earlier draft.

Catherine Deneuve and Isabella Rossellini both did screen tests for the role of Francesca, but Eastwood advocated for Meryl Streep from the very beginning despite Spielberg's initial reluctance.

Principal photography lasted only 42 days, wrapping on November 1, 1994, ten days ahead of Eastwood's planned 52-day schedule.

Eastwood filmed the story chronologically from Francesca's point of view, explaining it was important because the actors, like the characters, were getting to know each other in real time.

The film was shot on location in Madison County, Iowa, including the town of Winterset, as well as in Adel in Dallas County.

The MPAA initially gave the film an R rating because of a sarcastic line of dialogue spoken by Francesca ("Or should we just fuck on the linoleum one last time?"), but Eastwood successfully appealed and the rating was lowered to PG-13.

The film was the number one movie at the Japanese box office for nine consecutive weeks, grossing over $35 million there, and it opened at number two in the US, behind Casper, which coincidentally featured a cameo by Eastwood.