Distributors usually worry about things like "is this film going to make money" and "should we test it for audience reaction?" I do not know if the latter took place, but I can see this happening, and I can see them not being pleased with the results. Theaters are not pleased with movies that do not draw well, particularly at times like Christmas. If theaters have a choice between "Ride With the Devil" and "Terminator 27"--which they believe is going to rake money in, hand over fist--guess which film they are going to book?
Then there are the reviews. I think someone is being kind when they say there were many excellent reviews. Well, that depends on who was doing the reviewing. While there were those who did rave about it, there were those that didn't. I think on balance the polite term for the reviews was mixed. If I had to sum up the reviews I read, I'd say the reviewers gave it credit for historical accuracy, but described the pace of the film as slow and plodding for most movie goers.
Granted, the film did not have the release of a Terminator film, to use that example again. But in all honesty, who was really expecting that?
In any case, "Ride with the Devil" lingered in theaters through January, after a late November release. It's take at the American box office: $635,000. On a $35-38 million dollar movie. Ang Lee's name couldn't carry this film, as most of the actors were still relative unknowns in late 1999.
I'm not sure what the DVD take was, but that's where studios hope to recoup money on films that don't do well at the box office. I can only imagine the repackaging was done to enhance this possibility, which seems ironic given that Jeffrey Wright had already had some acclaim as an actor--more than some of his co-stars at that point. Also, if you look at the original advertising, how could you tell he was a Confederate?
(By the way, let's not forget that John Noland was not the only black riding with Quantrill. A Henry Wilson and a John Lobb also are given that credit.)
Friends I talked to who saw the film had perhaps had a take on the film that explains much. Please note that these people are not people who study the Civil War like some of us do. Their knowledge of the War is very basic. Their complaint was that there could have been a bit more of a "set-up" at the beginning of the film. They did not see this as a Civil War film because they did not understand the guerrilla nature of the war, and so they were a bit lost during most of the film.
While more has been written about the war in the Trans-Mississippi in recent years, it may be that "Ride With the Devil" was just ahead of its time as far as being understood by the general movie-going public.