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.
Christopher Guest and Nicolas Guest play the weaselly Ford brothers, and have almost nothing to do except act as suspicious as possible in their very few scenes, possibly as a result of being last minute replacements for the Bridges Brothers, Jeff and Beau. Dennis Quaid plays Ed Miller, who is much smarter and handsomer than the Ed Miller played by Garret Dilahunt in TAOJJBTCRF, but still manages to get himself kicked out of the gang for needlessly murdering people. His brother Clell Miller (Randy Quaid) stays with the gang, but later proves that murderous incompetence runs in the family when he plans the gang's disastrous Northfield robbery.
The Younger brothers are played by David Carradine, Keith Carradine, and Robert Carradine and are ironically more central characters to this film than the James Brothers. Stacy Keach and his less famous brother James Keach produced this film, and star as Frank and Jesse James respectively. Jesse is bizarrely not the spotlighted character in the story, and probably not even one of the top five most important characters here. Between robberies, the other men drink, gamble and chase women, but Jesse is already married, and returns home to his dour wife to have dull conversations from time to time. Frank James has much more prominence, and not just because of Stacy Keach's mustache's power to draw the camera towards itself.
The real main character is Cole Younger, a wry gunslinger played by David Carradine, who enjoys the most lengthy subplots, including a trip to Texas to fight for the love of Bella Starr, a famous lady outlaw for reason changed to a famous prostitute here, against her new beau. Starr is played by Pamela Reed, most famous nowadays for Kindergarten Cop and her role as Marlene Griggs-Knope on Park And Recreation; I'm sure her and Paul Schneider used to have discussions about what it was like to star in Jesse James movies. Her new beau is played by James Remar, possibly as a native American, who quickly challenges Carradine to a knife fight that wrecks most of the bar, sheds plenty of blood, and solves nothing.
The TAOJJBTCRF features Jesse James during the last year or so of his life, when he was hard up for quality partners or well-planned robberies, but this film is set mostly during the golden days. The James-Younger gang is so well-liked by the Missouri populace that out-of-state Pinkerton detectives have to be hired to hunt them, and their attempts to hunt for the gang seem utterly hopeless; the land is foreign, and the natives are hostile. They might as well be soldiers in another country, on the opposite side of the globe dealing with thousand year old customs and languages they only hope to properly understand. All the Pinkertons manage for most of the story is to drive public sympathy further towards the James-Younger gang.
Just like in a crime movie such as Goodfellas, the good times have to end eventually. Hundreds of hired men roam the state searching for them, so the gang decides to head to Minnesota to rob the Northfield bank, but it turns into a protracted gun battle that leaves every single man at best severely wounded. The signature Peckinpah battle shot, someone falling from somewhere in slow-motion intercut with several other full speed occurrences elsewhere, shows up in the hellish melee. The earlier gun battles of the film, a foggy nighttime ambush and a standoff in a barn in particular, are very small tastes of just how bad things will get when they get bad. When your best option to escape being shot (shot more) is to ride your horse through one window and then out another, you know you're in a tight spot.
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