USA: Cowboys

How the West was Won (1962)
Mountain men, Erie Canal, the rivers, the plains, the mountains, the Civil War, the railroad and the outlaws
Into the West (2005)
TV mini-series about the West from perspectives of a white settler family and a native American family
Meek’s Cutoff (2010)
1845 wagon train travel on the Oregon Trail where they lose their way on a supposed short-cut
The Oregon Trail (1959)
Experiences of a wagon train on the Oregon Trail
Donner Pass: The Road to Survival (1978)
Some of the settlers stranded in the northern Sierra Nevada mountains near Truckee, California in the winter of 1846 turn to cannibalism to survive
Lonesome Dove (1989)
C. 1866, based on cattle drivers Oliver Loving and Charles Goodnight out of Texas
Red River (1948)
1867, Chisholm Trail to Abilene, John Wayne
Abilene Town (1946)
At the end of the Chisholm Trail
Thousand Pieces of Gold (1990)
Chinese immigrant woman in the American Old West sold to be wife/slave to a prospector
Heaven’s Gate (1980)
A war in Johnson County, Wyoming between the owners of large-scale ranches and the owners of small ranches in 1892
Wild Bill (1995)
Wild Bill Hickok
Hickok that is; 1866-1871, marshal in Kansas cowtowns, including Abilene
Young Bill Hickok (1940)
Wild Bill Hickok
B western
Calamity Jane (1953)
Wild Bill Hickok
Supposed friend of Hickok
Calamity Jane (1984)
Wild Bill Hickok
Starring Jane Alexander
The Plainsman (1936)
Wild Bill Hickok
Wild Bill Hickok, Buffalo Bill Cody, Calamity Jane and George Armstrong Custer
American Outlaws (2001)
Jesse James
James and Younger gangs
The Long Riders (1980)
Jesse James
James, Younger, Miller and Ford brothers
The Great Northfield Minnesota Raid (1972)
Jesse James
Ill-fated 1876 bank robbery by James and Younger gangs
The Great Missouri Raid (1951)
Jesse James
Jesse James and Youngers
Jesse James (1939)
Jesse James
Bank and train robber and a very bad man; 1866-1882
The Assassination of Jesse James by the Coward Robert Ford (2007)
Jesse James
Shows James as a bit of a psychopath, but still portrays him somewhat sympathetically
Cole Younger, Gunfighter (1958)
Jesse James
With Frank Lovejoy; revenge, romance and a trial
Bad Men of Missouri (1941)
Jesse James
The Youngers
When the Daltons Rode (1940)
The Daltons
Dalton gang in Indian Territory; 1891, first train robbery
The Last Ride of the Dalton Gang (1979)
The Daltons
Dalton gang of bank robbers
Wichita (1955)
Wyatt Earp
1874, Wyatt Earp tries to bring law and order to Wichita, Kansas
Wyatt Earp (1994)
Wyatt Earp
1876-1879 marshal of Dodge City, Kansas (my personal favorite western)
Tombstone (1993)
Wyatt Earp
Wyatt Earp in Tombstone, Arizona; gunfight at O.K. Corral
Dodge City (1939)
Wyatt Earp
Composite fictional hero
Hour of the Gun (1967)
Wyatt Earp
Earp & Doc Holliday form a posse to hunt Ike Clanton and his gang
Gunfight at the O.K. Corral (1957)
Wyatt Earp
Gunfight in 1881 Tombstone, AZ
Frontier Marshal (1939)
Wyatt Earp
Wyatt Earp and the fight at the O.K. Corral
The Gunfight at Dodge City (1959)
Wyatt Earp
Very loosely based on Ford County sheriff Bat Masterson
The Woman of the Town (1943)
Wyatt Earp
Story of murder in Dodge City of Dora Hand by Jim Kenedy, who was partly captured by a posse composed of Wyatt Earp, Bat Masterson and other famous lawmen
Billy the Kid (1930)
Billy the Kid
First kill 1877
Billy the Kid (1941)
Billy the Kid
With Robert Taylor
The Left-Handed Gun (1958)
Billy the Kid
Billy the Kid
Billy the Kid (1989)
Billy the Kid
Chisum (1970)
Billy the Kid
The Lincoln County War, involving Billy the Kid, in what became New Mexico
Young Guns (1988)
Billy the Kid
Six boys, including Billy the Kid, are hired as "regulators" for a rancher in the Lincoln County War; the best true version of Billy the Kid
Young Guns II (1990)
Billy the Kid
Billy the Kid plans an escape from jail
Butch Cassidy and the Sundance Kid (1969)
Butch Cassidy and the Sundance Kid
Bank robbers; 1896 forms the Wild Bunch
Butch and Sundance: The Early Days (1979)
Butch Cassidy and the Sundance Kid
Buffalo Bill (1944)
Buffalo Bill and Annie Oakley
Buffalo Bill Wild West Show formed 1883
Buffalo Bill & the Indians (1976)
Buffalo Bill and Annie Oakley
Pony Express Days (1940)
Buffalo Bill and Annie Oakley
Buffalo Bill and the Pony Express (which lasted from April 1860 to October 1861)
Annie Get Your Gun (1950)
Buffalo Bill and Annie Oakley
Musical about female sharpshooter in the Buffalo Bill Wild West Show
Annie Oakley (1935)
Buffalo Bill and Annie Oakley
Musical about female sharpshooter in the Buffalo Bill Wild West Show
Tall Tales and Legends: Annie Oakley (1985)
Buffalo Bill and Annie Oakley
Children's film from Shelly Duvall's Tall Tales and Legends