Morgan Freeman was originally approached to play the role of Frankie Dunn. But even before Clint Eastwood took on directing and starring roles, he decided to take the part of Eddie "Scrap-Iron" Dupris.
Hilary Swank contracted a bacterial infection from a blister she developed on her foot during training for her role. The infection was so serious that she almost had to be hospitalized for three weeks. Catching the infection in the nick of time, she instead chose to take a week off for medicated rest and didn't tell Clint Eastwood or the other producers of the film about the injury, because she didn't believe it was in character.
Producer Albert S. Ruddy loved the story and was determined to make it into a film and spent four years trying to find backers who were interested in helping him make it. "I couldn't get anybody interested", he said in an interview, "and I'm talking about people who are friends of mine, people I've done business with for years. They'd tell me "Who wants to see a movie about two old grizzled guys and a girl fighter?"" Eventually he found someone interested - Clint Eastwood. The actor-director read the script and said "It's a downer...but God, it's gorgeous".
The first shot of Frankie and Scrap in the gym office was filmed with a split diopter lens. This is a close-up accessory lens cut half so it changes the focal point of only half of the scene, allowing both the foreground on one side and background on the other side to appear sharp. Brian De Palma is famous for using this technique in his films.
Stuck in development hell for years with many studios rejecting it because of its relatively downbeat subject matter. Even Warner Brothers rejected it, despite their longstanding association with Clint Eastwood, refusing to put up the thirty million dollars required. Eastwood persuaded Lakeshore Entertainment's Tom Rosenberg to put up half the budget, along with Warner Bros.
Anjelica Huston originally brought the book "Rope Burns" to producer Albert S. Ruddy's attention, hoping that he would ask her to direct the film. (She guaranteed that he would cry after reading the "Million Dollar Baby" story, and he admits that he did.) However, by the time Ruddy acquired the rights, Huston was busy on another project.
"Rope Burns: Stories From the Corner," a collection of short stories based on the experiences of long-time fight manager and cut-man Jerry Boyd, writing under the pen name F.X. Toole, was published in 2000 by Harper Collins. Toole was seventy at the time, and had been writing and battling rejection letters for forty years. "Rope Burns" was his first published work. Soon after its publication, he was commissioned to write his first novel, an epic story set on the Texas-Mexico border. He died on September 2, 2002, at the age of 72, just before his novel was finished. "Rope Burns" was dedicated to Jerry's partner and longtime friend Dub Huntley.
One of two times when the presenter handing Eastwood an Oscar was Barbara Streisand. She previously handed him the Best Director Oscar of Unforgiven (1992). Before giving the second movie award to him, she said, "I would be very happy to give you this again, Clint."
One of two times when Clint Eastwood and Martin Scorsese would compete for Best Picture and Best Director at the Oscars. Clint Eastwood won this time, but four years later they would compete again with Scorsese winning for The Departed (2006) and Eastwood nominated for Letters From Iwo Jima (2006).
Though this was the only time Clint Eastwood and Albert S. Ruddy won Oscars together for Best Picture, this wasn't the first time they were on stage for the Oscars. Clint Eastwood handed Albert S. Ruddy the Best Picture Oscar for the Godfather (1972) in 1973.
One of three Warner Bros. movies in a row where the Best Picture winner co-stars Morgan Freeman. The other two are Driving Miss Daisy (1989) and Unforgiven (1992). The Departed (2006) would be the first Warner Bros. Best Picture Oscar without Morgan Freeman since Amadeus (1984).
Of the three Best Picture Oscar winners featuring Morgan Freeman, this is the only one where he also won the Oscar for Best Supporting Actor. He was nominated for Best Supporting Actor in Driving Miss Daisy (1989).
The trivia items below may give away important plot points.
Probably one of the key features to the film being such a success was that no one had divulged the gutpunch twist that occurs towards the end of the movie, taking it in a whole new direction. People were going to see what they thought was a female boxing movie, and coming out overwhelmed by having seen a searing account of euthanasia.