Top 10 Terrible Jobs Boys Have Endured Through History

by Marcus Ribeiro

When we think of child labor today, we often picture modern‑day exploitation, but the past is littered with stories of boys thrust into the hardest, most unforgiving work imaginable. This top 10 terrible list journeys through recent Western history to reveal ten of the worst occupations that young lads were compelled to bear – jobs that adult men either shunned or simply couldn’t perform because of sheer size or social constraints. Strap in for a grim, yet fascinating, tour of history’s toughest boy‑jobs.

Why These Are the Top 10 Terrible Jobs for Boys

10 Farming

Child labor on a historic farm field - top 10 terrible jobs for boys

Working the fields as a child remains a reality on many family farms today, yet in earlier eras boys were dispatched wherever labor was needed, often under brutal conditions. They toiled for endless hours beneath a scorching sun, earning a pittance, with little mercy if illness struck or fatigue set in. While girls might have been relegated to sorting produce, boys endured the most grueling tasks.

Employers capitalized on the almost free labor that youngsters provided, especially during the Great Depression and the Dust Bowl, a time when profit margins were razor‑thin and the world reeled from World War I. The relentless economic strain forced families to rely on their children’s sweat to survive.

In the United States, child labor in agriculture was largely outlawed in 1938 as part of New Deal reforms aimed at reducing unemployment among adults. By raising wage standards and encouraging unionization, the law finally allowed children to experience genuine childhood for the first time in modern history.

9 Picolo

Young picolo cleaning a restaurant kitchen - top 10 terrible jobs for boys

Ludwig Bemelmans, famed author of the Madeline books, chronicled the grim existence of the picolo in his memoir When You Lunch With The Emperor. He described his own teenage years as an immigrant boy from Austria working at New York’s Ritz during the Great Depression, detailing the squalid conditions that defined the picolo’s life.

He wrote, “The child picolo is an institution in all European restaurants. His head barely reaches above the table; his ears are red and stand out, because everybody pulls them. And when he is a man he will still pull his head quickly to one side if anyone close to him suddenly moves, because he always did that to soften the blows that rained on him from the proprietor down to the last chambermaid; they hit him mostly out of habit.” He went on to observe that an aging waiter, bent over a chair, revealed a boy turned old, his feet crippled from a lifetime of servitude.

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The picolo’s day began at six‑in‑the‑morning and stretched to eleven p.m., encompassing every vile task no one else wanted: cleaning ashtrays, scraping plates, folding newspapers, washing dishes, and perpetually bowing to superiors. Though grueling, this role was not the absolute worst among the ten we examine.

8 Apprenticeships

Young apprentice learning a trade - top 10 terrible jobs for boys

Apprenticeships typically began for boys between ten and fourteen years old. Bemelmans noted, “the picolo was looked upon with envy by the apprentices of plumbers and cobblers; they had the red ears, too, but not enough to eat, and no cigarettes, no drinks, no tips.” In medieval times, a boy even had to pay for his apprenticeship, making it a rare case where youths were compensated for work in the 19th and 20th centuries.

These positions were undeniably arduous, and masters often meted out punishments liberally. Yet, unlike many other entries on this list, apprenticeships offered a relatively clear path to a stable, well‑paid career once the training concluded—a beacon of hope amid widespread hunger and poverty.

7 Cannery Worker

Child working in a fish cannery – top 10 terrible jobs for boys

Canery labor demanded long hours in icy Atlantic winters, where boys chopped, packed, and hauled fish and other foods. As a relatively new industry, canneries relied heavily on unskilled, low‑cost labor. Children as young as nine earned as little as five cents per box they processed.

The environment was perilous: dangerous cutting tools and mechanical canning machines that sliced and sealed metal posed constant threats. The sheer brutality of the work would have been daunting even for adult men, let alone youngsters.

Many of these factories were run by well‑meaning individuals who believed they were offering a better life to these children. As C.S. Lewis famously observed, “Of all tyrannies, a tyranny sincerely exercised for the good of its victims may be the most oppressive… it would be better to live under robber barons than under omnipotent moral busybodies.”

6 Bootblack (Shoeshine Boy)

Shoeshine boy polishing shoes on a city street – top 10 terrible jobs for boys

Legend has it that Joe Kennedy, father of President John F. Kennedy, received a stock tip from a shoeshine boy and promptly sold his holdings, thereby escaping the crash that ushered in the Great Depression. While anecdotal, the story underscores the precariousness of the bootblack’s existence.

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The trade was fierce: boys fought over corners, endured seven‑day weeks rain or shine, and survived on meager earnings. Those who could afford the expensive polish and equipment fared slightly better, but the job remained grueling.

The earliest known photograph of a person shows a man having his shoes polished by a bootblack, taken in 1838. That image also captures Pope Gregory XVI, the last pontiff who was a simple priest before his election, and who condemned the Atlantic slave trade.

In popular culture, the character Enoch “Nucky” Thompson from Boardwalk Empire credits his rise to reading Horatio Alger’s 1867 novel Ragged Dick, a story about a poor New York boy who blacked boots and climbed the social ladder through perseverance, thrift, and cleverness. The novel, a classic bildungsroman, epitomized the American Dream and remains recommended reading for both teens and adults.

5 Cotton Mill Worker

Young cotton mill worker operating machinery – top 10 terrible jobs for boys

The invention of the cotton gin and subsequent mechanization ushered in a new era for the post‑slavery West. After the Civil War, the abolition of slavery created a cotton shortage in Europe, prompting rapid industrial growth in the United States.

These factories ran faster, more accurately, and far more dangerously than human hands. Safety measures were minimal, and accidents were common. Twelve‑year‑old Giles Newsom, in 1912, lost two fingers when his arm was caught in a spinning machine’s gears—a grim reminder of the hazards faced by child laborers.

Family reactions to such injuries were often starkly pragmatic. One aunt lamented, “Now he’s jes got to where he could be of some help to his ma an’ then this happens and he can’t never work no more like he oughter.” This cold assessment highlights how child labor was essential for survival before modern banking and credit systems.

4 Soldier

Young child soldier in uniform – top 10 terrible jobs for boys

Child soldiers are a grim reality today, but their history stretches back to ancient Rome, where boys as young as fourteen were conscripted. In more recent conflicts, such as 1990s El Salvador, boys fought for rebel groups, and throughout the Balkans, child soldiers were a tragic staple of war.

One of the most striking historical cases is that of Momcilo Gavric, who joined a Serbian unit at seven and became a corporal by eight after his family was murdered. Orphaned, he sought vengeance and later studied in England before returning to Serbia, where he lived to 86, commemorated by numerous monuments.

While Gavric’s tale reads like a fairy‑tale, the broader practice of employing children in combat remains abhorrent. Fortunately, most Western nations now enforce strict laws prohibiting child soldiers.

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3 Prostitute

Boy prostitute on a 1970s Times Square street – top 10 terrible jobs for boys

Perhaps the lowest rung on this list is child prostitution, a tragic occupation still prevalent today. While often associated with girls, boys have historically been forced into the trade as well. In Victorian England, Jack Saul publicly declared himself a “professional Mary‑ann” at eighteen, revealing a career that began in childhood.

Rumors linked Saul to Prince Albert, grandson of Queen Victoria, suggesting a scandalous liaison. Prostitution was especially common among Catholic boys, who faced severe discrimination in England. Many of these youths were effectively enslaved by pimps and gangs.

Modern examples include 1970s Times Square, where two boy prostitutes haggled with potential clients, illustrating the continued hidden nature of this exploitation.

2 Mine Worker

Child miner with oil‑wick lamp working underground – top 10 terrible jobs for boys

While today many parents fret over video‑games and YouTube binges, we should remember the boys who spent their entire childhood deep beneath the earth, performing menial tasks for miners who hauled coal to power the world.

These youngsters, like the boy pictured in 1908 with an oil‑wick lamp, worked from 7 a.m. to 5:30 p.m., driving animals that pulled coal wagons, opening and closing safety doors, and handling any job suited to their small frames.

The conditions were unforgiving: lung disease, relentless physical labor, and the ever‑present danger of a mine collapse. The boy’s eyes in the photograph betray a stark awareness of the mortal risk surrounding him.

1 Chimney Sweep

Young chimney sweep climbing a rooftop – top 10 terrible jobs for boys

Perhaps the most iconic of all terrible boy‑jobs, chimney sweeping often ended in tragedy. After the Great Fire of London in 1666, boys as young as four were bought from their parents and forced into cramped, hazardous chimneys armed only with brushes.

A typical day involved sweeping from sunrise until dusk, then collapsing onto a floor in the master’s dilapidated lodging for a meager meal. Every morning, perched on a rooftop, a sweep faced the chilling prospect that today’s chimney could be the one that claimed his life—whether by a fall, suffocation, or becoming hopelessly wedged.

Many of these children remain entombed within London’s chimneys, with rumors even suggesting that the British Houses of Parliament conceal their tiny corpses. For those eager to explore further, British Chimney Sweeps: Five Centuries of Chimney Sweeping offers a comprehensive look at this dark chapter of Victorian England.

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