Jesse and his elder brother, Frank, fought as Confederate guerrillas with the bushwacking Quantrill's Raiders during the American Civil War. In sharp contrast to the later myth of the James as poor farmers and soldiers turning to war, the James family were relatively well-off. They had a substantial farm growing hemp and tobacco before the Civil War, and they owned seven slaves. The Younger Family (Cole, Jim, Bob and John), future allies and compatriots of James' gang were in fact descendants of the richest slaveowning family in Jackson County, Missouri. The James and Younger family served alongside the notorious William Quantrill and Bloody Bill Anderson in several guerrilla wars in Kansas and Missouri against the Jayhawkers, anti-slavery militants from Kansas. They were involved in the Lawrence and Centralia Massacres in particular.
His criminal fame took off after Anti-Reconstruction newspaper editorials claimed that Jesse and Frank wanted revenge for the appropriation of their family and neighbors' farms by investors who wanted to build a railroad there. Their gang of bitter ex-Confederates sabotaged railroad constructions and they robbed banks where the investors kept their money. Even during his life, the James and Younger gangs were seen as folk heroes and living legends, which elevated Jesse James as a Robin Hood character, who rebelled against the government and gave his stolen goods to the poor. While it's true that in only two train hold-ups passengers were robbed since James typically limited himself to the express safe in the baggage car, the gang always kept the money to themselves. They also killed civilians and took medicine intended for the poor and needy.
An attempt to rob a bank in Northfield, Minnesota in 1876 was met with whole bunch of gunfire and the Youngers were arrested. Jesse and Frank managed to escape and kept hidden for three years. In 1879 they started a new gang robbing banks and trains, specifically targeting those owned by Republicans as part of their revenge for the civil war. In 1882 the 34-year-old Jesse was murdered by one of his own gang members, Robert Ford.
Jesse James' portrayal in fiction provides examples of...
- Dime Novel: He was such a legendary character that he became subject of these cheap novels after death.
- Folk Hero: Because of the Robin Hood myth surrounding his character he's often thought to have been a Gentleman Thief who stole from the rich and gave to the poor. This made him a hero in 19th-century American folklore to the point that the man who finally murdered him, Robert Ford, was branded as a coward, for shooting Jesse James in the back. In reality James' gang were ordinary robbers and never shared their profits with anyone but themselves. Indeed they often robbed trains containing medicine for the poor.
- Freudian Excuse: Romantic media portrayals such as the folk song "Jesse James" casts him as a Confederate veteran branded as an outcast during the Reconstruction era, with Jesse James being one of many Confederate veterans who ended up as a bandit after the Civil War. The James family were in fact well-off, and Jesse and Frank James did not see a great deal of battle action, their key activities being that of pro-slavery bushwhackers.
- Historical Hero Upgrade: Compared to Billy the Kid his legacy is a bit more positive in the public perception, despite all evidence to the contrary. This is because unlike Billy Jesse James benefited from the "Lost Cause" hagiography. Most Jesse James movies neglects the time he and his brother served under William Quantrill in Missouri during The American Civil War, where they served, in the words of one historian, as a "death squad" against the local population of Union sympathizers and massacred not only civilians but also Union POWs. Most portrayals evoke Jesse James with an anti-authoritarian romanticism rather than anything related to the actual political reality.
James McPherson It is true...that [James] was daring, brave, and capable of astonishing feats of endurance, but it is also true that most of his homicide victims after the Civil War were unarmed and helpless, as were many of the men he murdered as a teenage guerrilla. So why do so many still worship him as a hero?...The answer lies in what both contemporaries and later commentators have chosen to see in Jesse James—Robin Hood, social bandit, scourge of capitalism—rather than in what he really stood for.
- Just Like Robin Hood: Like many other historical outlaws he has been depicted in this manner by ballads, dime novels and movies. It is doubtful that such a reputation is justified, however. Especially the notion of him (like so many others listed) "stealing from the rich and giving to the poor", which has little to no evidence supporting it.
- Outlaw: Together with Billy the Kid, the most famous outlaw of The Wild West.
- Shocking Defeat Legacy: To this day, Northfield, Minnesota celebrates the first weekend of September as "The Defeat of Jesse James Days". Jesse and Frank escaped, but two of their gang were left dead in the streets of Northfield and everyone else was nabbed by the ensuing manhunt. The James brothers never regained that level of fame and fortune, ending up as small-time crooks before Robert Ford put an end to it permanently.
Appearances in popular culture:
- Lucky Luke: Appears at the end of Billy The Kid trying to scare the villagers of that town in order to give him all his loot. Unfortunately they are no longer afraid of outlaws and simply tar and feather him. He returns in a much larger role in the album Jesse James'. In this album he fancies himself the new Robin Hood, but is a bit reluctant about the "giving to the poor" part. His brother Frank has a brilliant idea: Jesse will give everything he steals to him, Frank, who currently is poor; by doing this, Jesse will become poor too, so Frank will give everything back to him, and so on. Robin-Hooding stays in the family. Another amusing joke is that Frank is such a William Shakespeare fan that he quotes lines from his plays in fitting situations.
- The Flash: The first Trickster, James Jesse admired Jesse James since childhood and decided to pull the modern equivalent of train robberies by robbing airplanes—in midair.
- Wonder Woman (1942): A couple of invading trouble making aliens rob a train disguised as Billy the Kid and Jesse James in #107, allowing for a short flashback explaining each outlaws' place in popular culture.
- Jesse James (1939) stars Tyrone Power as Jesse, Henry Fonda as Frank and John Carradine as Bob Ford.
- I Shot Jesse James (1949) by Samuel Fuller features Jesse James in the opening sequence and then focuses on Robert Ford who is given a highly sympathetic portrayal. Fuller himself stated that he disliked the Jesse James myth and according to him, Robert Ford, was more sympathetic or likable to him.
- Brad Pitt portrays him in The Assassination of Jesse James by the Coward Robert Ford. The most recent and critically acclaimed movie adaptation of Jesse James, praised for being more historically accurate than older films. Nick Cave also wrote the song "The Ballad of Jesse James" about him.
- Appears in the weird movie Jesse James Meets Frankenstein's Daughter.
- The Great Northfield Minnesota Raid, a 1972 Western which may be one of the first films to portray Jesse as the thug that he was. (Probably because the film was trying to portray Cole Younger as the badass one)
- Subject of the film The Long Riders, best known for casting actual brothers as the James and Younger siblings.
- Jesse James is one of the eponymous outlaws to appear in The Three Stooges feature film The Outlaws IS Coming!.
- The Brady Bunch: In the episode "Bobby's Hero", Bobby becomes so fascinated with Jesse James that he brings a toy gun to school and makes his teachers and parents very concerned. Finally, Jethroe Collins, the (fictional) son of one of James's victims, tells Bobby how his father was gunned down by James, and Bobby's subsequent Opinion-Changing Dream makes him change his mind. For such a light-hearted 1970s sitcom, it's one of the few Hollywood productions that depicted James accurately as a horrifying Ax-Crazy killer. While Collins was a fictional character, the story he tells is pulled from historical accounts of James's murders.
- Plays in several episodes of The Young Riders.
- James appears in three episodes of The Pinkertons: The pilot, where he participates in the very first Train Job; "Frontier Desperados", where he helps the future Belle Starr kidnap her husband (and becomes her lover as well); and "To the Death", where he's the main villain.
- James and his gang, along with his brother, went up against Al Capone in season 2 of Deadliest Warrior. His gang wins. And he's saved from getting a No-Holds-Barred Beatdown from Capone by his brother, Frank, leading to the only team that has had more than one survivor at the end of the match.
- Monster Garage's host Jesse James' Discovery Channel profile claims the host is descended from the outlaw.
- He turns up in the Timeless episode "The Murder of Jesse James," where he's portrayed as a once-idealistic man whose life of fighting and killing has turned him into everything he used to hate.
- The Twilight Zone (1959): In "Showdown with Rance McGrew", Rance McGrew is an arrogant actor with way too much creative control who stars in a Western show where he never loses and outlaws like Jesse James are weaklings and cowards. He abruptly finds himself in the real Wild West where Jesse James says he and his fellow outlaws are displeased with how they are portrayed on his show. He challenges Rance to a duel with real guns, and Rance quickly folds and begs for mercy. Rance finds himself back in the present, but Jesse James is now his agent who revises the show so that the outlaws are tougher.
- The traditional folk song "Jesse James" dates to shortly after Jesse's death, was first recorded in 1919, and has since been recorded in literally hundreds of versions including by Woody Guthrie, The Pogues on Run, Sodomy & the Lash, and Bruce Springsteen on The Seeger Sessions.
- Serge Gainsbourg mentions him at the start of his song "Bonnie & Clyde".
- Warren Zevon wrote another sympathetic song, "Frank and Jesse James".
- Country musician Jessie James takes her name from him.
- Bob Dylan's "Outlaw Blues" from Bringing It All Back Home namedrops Jesse James and his assassin Robert Ford.
I might look like Robert Ford, but I feel just like a Jesse James.
- Referenced in "Bad Meets Evil" from Eminem's The Slim Shady LP
- Namechecked in Cher's 1989 hit "Just Like Jesse James".
- Country singer-songwriter Paul Kennerly wrote a very star-studded 1980 concept album based on James' life, featuring Johnny Cash, Charlie Daniels, Emmylou Harris and Levon Helm, with comics artist Howard Chaykin drawing the cover art.
- Silas Greaves from Call of Juarez: Gunslinger claims to have outgunned Jesse. When someone points out that James was killed by Robert Ford, he quickly corrects himself that he only wounded him and that this defeat was so embarrassing, Jesse never told anyone about it.
- Gunfighter: The Legend of Jesse James is a Light Gun Game where players assume the role of Jesse to take down a corrupt sheriff. The Younger brothers gets to play key roles in both games as well, notably Bob Younger who is the second game's main villain.
- A severed hand that supposedly belonged to Jessie James shows up in a a Crappy Carnival in Sam & Max Hit the Road, and re-appears in its follow-up. It's heavily implied in both to be a complete fake - In the former, Sam mentions that it's still twitching when he takes it, and the latter has him use a carbon dater that proclaims it to be only 15 years old. Sam seems to be in denial about that, though.