There is very little to admire about Jesse James, and yet Americans for generations have.
Jesse James, 1876.
James, as everyone knows, was the Missouri born leader of what was essentially a family, and indeed an ethnic, gang based in Missouri that successfully operated for a time in the Post Civil War Missouri region. James and his siblings had been exposed to extreme violence as Confederate guerillas during the war and were endowed with the "Little Dixie" region of Missouri's views on the world, none of which would draw sympathy from many people today, but which allowed them to operate relatively safely in the region in spite of their criminal activities due to the feeling that they were, in some ways, continuing the Southern cause. Those views didn't hold up everywhere in Missouri and they certainly didn't outside of the state, which brought the end of the gang following an extremely failed attempt to raid a bank in Northfield Minnesota.
In spite of the fact that James-Younger gang is not admirable in any sense, they've been the topic of fascination of Americans since their very own time and therefore have been the subject of numerous movies. Indeed, there are at least twenty screen depiction of James and his gang including one television series from 1965-66. Numerous Americans claim to be related or descendant from James no matter how dubious their claims may be and, just like for Butch Cassidy, plenty of people claim that James didn't die from a bullet to the back of the head fired by Bob Ford in 1882. He did.
I haven't seen most of the films that portray James, but there are three that really stand out that a lot of people have seen and which are worth mentioning. I'll deal with them here, in chronological order.
The Great Northfield Minnesota Raid is a 1972 film limited to the raid on Northfield Minnesota and the events leading up to it. It has a notable cast, including a young Robert Duvall as James and Cliff Robertson as Cole Younger. It's a fictionalized version of the raid containing fanciful and strained elements but it's really notable for Duvall's portray of James as a homicidal maniac. It's worth watching for that reason as Duvall, in a portrayal that perhaps could be regarded as an example of an early anti Western, portrays a really disturbing James which served to strip him from the heroic portrayal that was more common up until then. Robertson, however, steals the show with a really eclectic portrayal of an intellectually curious Younger.
The film isn't bad in terms of material details.
Returning, however, to a more sympathetic portrayal is the sweeping 1980 The Long Riders which is really unique for casting actors who were in fact brothers to play characters in the true story who were actually brothers. While this film is only eight years later than The Great Northfield Minnesota Raid it placed really close attention to material details and has the look and feel of mid 19th Century Missouri right.
As noted, the film made use of actual siblings, with the Keach bothers playing the James brothers, the Caradine brothers playing the Younger brothers, the Quaids playing the Miller brothers, and the Guests playing Bob and Charley Ford. In some odd way that makes the film feel that much more accurate.
This film starts before the Northfield Minnesota Raid and also features James Whitmore, Jr. as a Pinkerton agent. It concludes with Ford's killing of James.
As does the 2007 film The Assassination of Jesse James by the Coward Robert Ford. The awkwardly long title of the film in some ways sets this film up nicely for what it is, a beautifully filmed and very accurate movie which starts after the Northfield Minnesota Raid and deals with the gang and its central post raid figures. Extremely moody and presented almost like a narrated book, Brad Pitt's portrayal of James as a highly intelligent, charismatic, and mentally deranged figure is brilliant. Casely Affleck's Robert Ford is really the main focus of the film and his portrayal of James "assassin" is likewise brilliantly done. The portrayals are so effective that they risk actually defining the real individuals, which may not be fair in context.
This film is superb on material details and it has the look and feel of mid 19th Century Missouri, and then briefly late 19th Century Colorado, just right. The film concludes with the death of Bob Ford, showing how its focus is really on the Ford character, not on James. In some ways its a subtle morality tale which none of the other James movies are. If a person was going to watch just one of these films, this one would be the one to watch.