THE GREAT NORTHFIELD MINNESOTA RAID (1972)

Another Jesse James picture?  What makes this one different?  This film from director Philip Kaufman has a narrow focus, concerning itself mainly with the titular event, which showed up as the finale of The Long Riders, but is portrayed much differently here and serves as the bulk of the film.  James is one of our twin protagonists, the other being Cole Younger again.  Jesse James is played by Robert Duvall (same year as The Godfather) but again his depiction is far cry from what might be expected.  This James is ignorant, careless, sloppy, fanatical, shortsighted, petty and seems to have become such a great outlaw solely by luck and good company.  Cole Younger, by far the wiser of the two, is played by Cliff Robertson who is best known nowadays as Uncle Ben in the Spiderman Trilogy.  Dirtier and grimier than most westerns, with loads more period language thrown in to boot, this film seems more authentic even when its differs from history.

THE LONG RIDERS (1980)

Jesse James's time as the leader of the James-Younger gang is the focus of this crowd-pleasing adventure about robbing banks and trains, wooing women, and defending southern honor against Yankee devils.  Its such a good time that its almost a shame the story follows history and ends with pretty much everybody dead or in jail.  This film stands out for a number of reasons.  Walter Hill's stylish direction makes use of gratuitous slow motion and even more gratuitous (not to mention copious) squibs during the gunfights which resemble his mentor Sam Peckinpah's bloodbaths like The Wild Bunch, and his decision to shoot in Georgia makes this the greenest, lushest, most verdant western I've ever seen.  The period score by Ry Cooder is also fantastic, particularly the opening number played over oneiric footage of the men riding through endless green fields with the sky bright above them and his rendition of 'I'm A Good Old Rebel' which sounds much better here than it did in The Assassination of Jesse James by The Coward Robert Ford when Jeremy Renner sang it.  But the most notable and famous feature of this film is the cast: four sets of actor brothers playing four sets of outlaw brothers.

THE ASSASSINATION OF JESSE JAMES BY THE COWARD ROBERT FORD (2007)

The internets claim that when Brad Pitt signed onto this film he had it put in his contract that the studio could not modify the title.  That may be the first thing he did to ensure the greatness of this movie, but the second and more important thing he did is give a brilliant performance.  Pitt as Jesse James is a far cry from what might be expected from the man known as the Robin Hood of postbellum Missouri.  He is not a noble leader of a band of merry men, and he does not steal from the rich to give to the poor; he is boss to a hired pack of thieves and killers, and he steals because that is what he trained to do as a youth in the Civil War and he knows nothing else.  In the last year and so many months of his life that this film dramatizes, James is a paranoid psychotic, murdering in cold blood anyone who might conspire to turn him over to the authorities despite also trusting worse and worse men in his desperation to recruit a posse, with violent mood swings such as a sobbing fit immediately following the extended needless beating and interrogation of a thirteen year old boy.  He is not Robin Hood.