“The phrase "riding shotgun" is a holdover from stagecoach days. But apparently it isn't. From what we can tell, the expression didn't arise until long after the stagecoach era ended.
The term shotgun, meaning a smoothbore long weapon that fires a load of shot instead of a single ball or bullet, dates to 1776. A frontier term, "shotgun" was first recorded in Kentucky and noted by James Fenimore Cooper as part of "the language of the west." The weapon was also called a two-shoot gun, a scatter-gun, and a few other terms.
Though disdained by marksmen, the shotgun was the weapon of choice among pony express riders and stagecoach guards - indeed, in the late 1880s and early 1890s, an express messenger was called a "shotgun messenger." A shotgun scattered pellets, making it easy to hit your target at short range. If the barrels were sawed off, the shot scattered over a wider area, an advantage if you were defending against a group (robbers or wolves, for instance). You didn't need to aim precisely, just point the gun in the right direction.
The Stevens Point Journal (Wisconsin) from September 9, 1891, says: "Of all the devices and inventions for the protection of treasure and circumvention of the road agent, the only one that has stood the test of time and experience is a big, ugly-tempered man with a sawed-off shotgun on the box ... [I]t is the business of the man with the sawed-off shotgun not to let [the robber] get the drop, but to blaze away as soon as he shows up. The gun is sawed off for the greater convenience of the messenger in potting road agents. It is loaded with buckshot and scatters like a charge of bribery fired into a California legislature." (We gently refrain from comment on the aptness of the analogy, a century and a decade later.)
So stagecoach guards rode shotgun - they just didn't call it that in the 1880s, as far as anyone has yet discovered. The term "riding shotgun" to refer to the guard sitting next to the driver doesn't emerge from the Old West but rather from movies and TV shows about the Old West. To date no one has found a cite for "riding shotgun" during the time stagecoaches were actually used.
The earliest usage we've found in pulp fiction occurs in the March 27, 1921 issue of the Washington Post's "Magazine of Fiction," in a story entitled "The Fighting Fool" by Dane Coolidge. The opening lines are:
"Lum Martin!" shouted McMonagle, owner of the Cow Ranch saloon, waving his finger in front of Benson's face, "that's the man - Lum Martin! He's ridin' shotgun for Wells Fargo - or was until last week - and he's over in my saloon right now, playin' solitaire!"
This Staff Report did provide an excuse to watch (again) the classic 1939 movie Stagecoach: Curly, the sheriff, says, "I'm gonna ride shotgun," and John Wayne expresses surprise at seeing him in fact riding shotgun later. So we have references from pulp fiction and from the movies (but not from the Old West itself) using the term "riding shotgun" to refer to the stagecoach guard.
Stagecoach revived interest in westerns as a movie genre; in the 1950s they became a staple of television, too. Not surprisingly, catchphrases from westerns soon found their way into everyday speech.
So when does "riding shotgun" get transferred from stagecoach to automobile? The Dictionary of Americanisms (1951) doesn't mention "riding shotgun." We're not sure whether absence of a phrase is evidence, but it's certainly indicative. The first usage in print relating to automobiles, is - ready? - 1954. Dropping "riding" and using the simple "shotgun" (as in "I call shotgun") to mean the passenger seat comes in the early 60s.
Thus, the sequence seems to be that the usage "shotgun guard" on a stagecoach in the Old West (say, the 1880s) evolved to "riding shotgun" in popular fiction about the Old West in the 1920s and 1930s, from there made its way into movies and television, was applied to automobiles in the 1950s, and finally was shortened to "shotgun" in the 1960s.
The term "shotgun" is also used colloquially to indicate an act performed under duress, as though at gunpoint. In the 1880s we read of "elections held under the shotgun system" and in 1903 we find the first reference to "shotgun wedding," which suggests a pregnant bride and a nervous groom getting hitched at the insistence of a shotgun-wielding father. Today we use shotgun wedding figuratively, but one suspects it may have been meant literally in 1903.”
Source(s):
I Hear American Talking, Stuart Berg Flexner (1976)

Dictionary of the American West, Winfred Blevins (1992)

Dictionary of American Regional English, edited by Joan Huston Hall, vol. 4

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