While history is one of my favorite things, the history of language is the epicenter of my favorite historical things to explore. For about two years, I did a blog series where I looked into the origins and true meaning of some of the most used (and my favorite) idioms and colloquial phrases in the United States. (Make sure you read all of the 10 part investigatory series to find out the meaning behind the most commonly used idioms: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, Extras.) Most were phrases you could have heard your grandma say while gossiping on the phone with her sister or overhear the older gentleman down at the corner store say while describing his nephew. Wherever you have heard them or if they were all new to you, the rich word nuggets add flavor to the word soup that is the English language. Today I will be revisiting the topic of ‘interesting idioms and colloquial phrases’ by adding a couple of which I never got the chance to dive into their meaning.
Today we will be expanding the blog series by investigating the history behind three Western-influenced phrases and one whose rhyme is only half of its past. We will look into the origins of:
“In like Flynn,” “Off the reservation,” “Riding Shotgun,” and “Off the Wagon.”

“In like Flynn” —
Origin: The cinematic ‘pirate accent‘ was an advent of Robert Newton in the 1950 Disney adaptation of Robert Louis Stevenson’s Treasure Island. The term swashbuckler is synonymous with another actor whose movie roles made him a staple in that genre, but his lifestyle off of the silver screen created the origin of this colloquial phrase. Erroll Flynn was a Famous silver screen swashbuckler whose portrayals, such as his portrayal of Robin Hood in 1938’s The Adventures of Robin Hood, solidified Flynn as a Hollywood star. He is remembered nowadays by his off-screen partying ladies’ man. Flynn enjoyed the notoriety (and women) his lifestyle brought him and even boasted about his ahem manhood and the numerous amount of lovers in his biography.
While using the word ‘in’ had been used to say that you were successful (either in luck, good fortune, or sexual conquest) for years before, it was the reference to being ‘in’ like Errol Flynn’ that took off. The earliest written use of the phrase ‘in like Flynn’ was in a February 1946 article from The Orem-Geneva Times (a Utah newspaper): Flying in it (a P-47 aircraft) is really luxurious, as the G.I.s say “We’re in like Flynn.” The phrase was used to reference his flamboyant lifestyle but also be used to reference his numerous sexual conquests, as shown in the sports section of The San Fransisco Examiner:
“Answer these questions correctly and your name is Flynn, meaning you’re in, provided you have two left feet and the written consent of your parents.”
San Fransisco Examiner
Errol’s sexual prowess was a nationwide topic after the popular romantic lead was on trial and ultimately acquitted of the statutory rape of a teenage girl in 1943.
Meaning: Successful, usually referencing finances, good fortune, or used for sexual/romantic connotation.

“Off the Reservation” —
Origin: While Errol Flynn’s most famous role was that of the eponymous hero Robin Hood, he starred as a cowboy hero in Westerns such as Dodge City, Santa Fe Trail, and San Antonio. Westerns were and are not only a part of American history but have had an impact on Pop Culture. The Westward Expansion in the United States truly impacted American History, and our next couple of infamous phrases come out of the American West. The sad part is that many use them with no real knowledge of its sometimes offensive past.
When using our first saying in an interview, the former first lady and former Presidential nominee Hillary Clinton immediately fell under scrutiny from all sides of the political spectrum. Used in movies like Wedding Crashers and even used by many of us in casual conversation, the phrase has an offensive past. After many natives died after being forced from their native lands, Native leaders like Crazy Horse and Sitting Bull fought as hard as they could against the American onslaught. After many years, Sitting Bull decided to take his people north into Canada and follow the buffalo. The Natives held many victories, so the American government decided to starve them out by destroying the one thing that they relied on more than most: the buffalo. The buffalo’s numbers dwindled, and the difficult decision of coming to terms and signing their freedom away by living on a reservation. The sole purpose of the Native American’s assimilation (forced to assimilate into the white man’s ways of farming, living, clothing, language, and even religion) was to ‘kill the Indian – Save the man.’ The common phrase ‘off the reservation’ was a prepositional phrase coined to refer to any Native American who tried to leave or were not living on the reservation. Many times used in writing in the late 1800s, including one documented occasion where the commissioner of Indian affairs received a telegram from a reservation in Oregon that said, “No Indians are off the reservation without authority. All my Indians are loyal and peaceable, and doing well.”
While “off the reservation” is not the most offensive insult or the most extreme racial slur, but I still don’t think that this phrase is okay to use in any context.
Meaning: While the literal meaning is for a Native American to leave the area reserved (hence the name reservation) for them, the extended definition is to engage in disruptive behavior that is unlike the norm.

“Riding Shotgun” —
Origin: Many of the areas once occupied by the Native Americans were the site of boomtowns. These boomtowns popped up in and around gold and silver mines in the part of America known as the Wild West. It was not only a dangerous terrain but transporting goods could be deadly. Bandits and hostile Native Americans would frequently rob stagecoaches and wagons that traveled in the Old West. To prevent the loss of expensive cargo in the mid-1800s, companies like Wells, Fargo & Co. would issue shotguns (a 10 or 12-gauge short, double barrel) the driver and guard to use as a defense on long routes. The shotgun issued to these ‘shotgun messengers’ was called a ‘coach guns,’ and the expression “riding shotgun” was derived from whoever was riding in the guard position. A famous example of a ‘shotgun rider’ was none other than infamous Wild West lawman (and some would consider outlaw) Wyatt Earp. When Wyatt first arrived in Tombstone, he took a job riding shotgun for Wells Fargo’s shipments of silver bullion. The phrase ‘riding shotgun’ was first used in print to describe Wyatt and subsequently his brother Morgan (who took over as the shotgun rider when Wyatt became sheriff of Pima County) in the 1905 novel The Sunset Trail by Alfred Henry Lewis. While describing one of Wyatt and Morgan’s occupation, he said that “they went often as guards–“riding shotgun,” it was called–when the stage bore unusual treasure.”
So next time you yell ‘shotgun’ as you rush to sit in the front seat of the car or infer that you are a ride-or-die friend of someone, think about the history of what it means to have that position.
Meaning: Modern meaning is to ride alongside the driver in a vehicle, while the original use was to describe the shotgun-wielding bodyguard of a stagecoach driver.

“Off the wagon” —
Origin: As the Wild West slowly lost its edge, big cities like New York and St. Louis were trying to become even more civilized. Civility came in many forms. One of these forms was the temperance movement coincides with another form that also works as the origin of our last phrase. Before the advent of paved roads, the dust from the dry dirt roads in town inevitably caused a cleanliness issue for the townspeople. Water carts, pulled by mules or horses, sprayed streets with water, and helped fight the dust from these dry roads. We link the use of water carts to the temperance movement because, during prohibition, people started referring to a person being ‘on the wagon’ if they were drinking water instead of alcohol. So as William Hamilton Anderson (superintendent of New York’s Anti-Saloon League) said in 1901, “No more falling off the water wagon.”
Meaning: Originally a reference to someone falling back on their old ways of drinking alcohol and is now used to refer to falling back on your old ways.
Images:
Featured Image – Errol Flynn in the American Western Virginia City, 1940 attributed to Warner Bros. – Source archive, Public Domain, https://commons.wikimedia.org/w/index.php?curid=82437552
Olivia de Havilland and Errol Flynn from the original trailer for The Adventures of Robin Hood, 1938 attributed to Warner Bros. – Original trailer, Public Domain, https://commons.wikimedia.org/w/index.php?curid=3568333
Chief Sitting Bull, Public Domain, https://commons.wikimedia.org/w/index.php?curid=540213
Riding Shotgun black & white scan of Montgomery’s The Beginner’s American History (1904), page 243., Public Domain, https://commons.wikimedia.org/w/index.php?curid=169616
A mule-drawn water wagon attributed to an Unknown author or not provided – U.S. National Archives and Records Administration, Public Domain, https://commons.wikimedia.org/w/index.php?curid=17159812
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