Nannie Doss is a name that sends cold shivers down the spine. Known infamously as the “Giggling Granny,” she was a seemingly sweet grandmother who left a trail of death behind her charming smile.

Behind the facade was a serial killer whose crimes spanned decades, targeting her own family and romantic partners. Here’s how history’s most chilling murderers shook thee society they lived in.

Nannie Doss, born in 1905 in Calhoun County, Alabama, had a troubled childhood. She suffered from a head injury when she was seven years old that may have contributed to her later behaviour. Her upbringing under a controlling father left her with a limited education and few social opportunities. These early experiences likely shaped the trajectory of her dark path.

At just 16 years old, Nannie married Charles “Charley” Braggs, a co-worker at the Linen Thread Company. The union was reportedly arranged by Nannie’s father. Their turbulent relationship was strained by the presence of Braggs’ controlling mother.

Between 1921 and 1927, the couple had four children but the marriage fell apart after two of their children died under suspicious circumstances, presumably food poisoning. Warned anonymously not to eat Nannie’s cooking, Braggs fled with their eldest daughter, Melvina, leaving their new-born, Florine, behind. They divorced in 1928, making Braggs the only one of Nannie’s husbands to escape her lethal tendencies.

Her subsequent relationships, however, revealed her sinister motives. Over the years, Nannie poisoned four of her husbands, hiding behind the guise of a grieving widow. Her signature poison? Arsenic, often administered in food or drinks. Investigators later discovered that her charming demeanour and ability to win people’s trust made it easy for her to avoid suspicion.

Shockingly, Nannie’s victims were not limited to her husbands. She also allegedly murdered her own children, grandchildren and other relatives, making her crimes all the more heinous. Her reasons varied, from financial gain to personal convenience, but the pattern of using arsenic remained consistent.

1920s: Two of Nannie’s young children died under suspicious circumstances, presumably food poisoning, during her first marriage.

Between 1929-1945: Nannie is suspected of killing her new-born granddaughter shortly after birth, as well as her two-year-old grandson, Robert, who died of asphyxia while in her care. She later collected a $500 life insurance policy on Robert.

1945: Nannie’s second husband, Frank Harrelson dubbed an “alcoholic”, dies via rat poisoning.

1950: Nannie’s third husband, Arlie Lanning, dubbed an “alcoholic womaniser”, also died from rat poisoning. Soon after, Nannie allegedly killed Lanning’s mother in a house fire.

1950: In the same year, Nannie’s sister Dovie died under suspicious circumstances, likely from poisoning.

1953: Nannie’s mother, Louisa, died after showing symptoms consistent with arsenic poisoning.

1953: In the same year, Nannie’s fourth husband, Richard Morton, died via arsenic poisoning.

1954: The death of Nannie’s final victim, her fifth husband, Samuel Doss, led to her arrest.

Suspicious of foul play, the physician who treated Samuel Doss persuaded Nannie to agree to an autopsy, suggesting it might help save lives by identifying the cause of her husband’s illness. The examination revealed a lethal dose of arsenic, enough to kill a horse. The doctor reported his findings to the authorities, leading to Nannie’s arrest.

During police interrogation, Nannie confessed to the murders of her four husbands in exchange for being allowed to keep a romance magazine. Nannie Doss insisted that her actions were not motivated by financial gain but by a desire for true romance. When she felt unfulfilled in a relationship, she would end it in the most chilling way and seek love elsewhere.

Subsequent exhumations confirmed that many of her victims had died from arsenic or rat poison.

Nannie’s eerie moniker, the “Giggling Granny,” came from her unsettling habit of giggling during police interrogations and trials. Her laughter seemed to mock the gravity of her crimes, unnerving everyone around her. This behaviour contributed to the media’s fascination with her and added an unsettling layer to her already horrifying reputation.

At 48 years old, Nannie faced the electric chair and was set to become the first woman executed in Oklahoma. However, two years later, a judge declared her insane, sparing her from execution. The judge later explained his reluctance to set a “poor precedent” by executing a woman, especially one with mental disabilities, according to the Encyclopaedia of Alabama.

In 1955, Nannie received a life sentence, which she reportedly welcomed with enthusiasm. She attributed her murderous tendencies to a childhood head injury that she claimed caused lifelong headaches.

Although Nannie was convicted of the deaths of her four husbands, investigators believe she killed at least 11 people, including her four husbands, mother, sister, two children, two grandchildren and her mother-in-law. Her chilling confessions captivated the nation and ensured her place in history as one of America’s most notorious female serial killers.

Nannie Doss died in prison in 1965, but her legacy endures as a macabre reminder of how appearances can be deceiving. Her story highlights the importance of vigilance, even in the face of a seemingly harmless smile.

• A Tell Media report