Bosman was born at Kuilsrivier, near Cape Town to an Afrikaner family, although he was raised with English as well as Afrikaans. While Bosman was still young, his family moved to Johannesburg where he went to school at Jeppe High School for Boys in Kensington. He was a contributor to the school magazine. When Bosman was sixteen, he started writing short stories for the national Sunday newspaper (the Sunday Times). He attended the University of the Witwatersrand submitting various pieces to student’s literary competitions.
Upon graduating, he accepted a teaching position in the Groot Marico district, in an Afrikaans language school. The area and the people inspired him and provided the background for all his best known short stories; the Oom Schalk Lourens series and the Voorkamer sketches. The Oom Schalk Lourens series features an older character with that name. the Voorkamer series are similarly all set in the Marico region.
During the school holidays in 1926, he returned to visit his family in Johannesburg. During an argument, he fired a rifle at his stepbrother and killed him.
Bosman was sentenced to death and moved to Death row at the Pretoria Central Prison. He was reprieved and sentenced to ten years with hard labour. In 1930, he was released on parole after serving half his sentence. His experiences formed the basis for his semi-autobiographical book, Cold Stone Jug.
He then started his own printing press company and was part of a literary set in Johannesburg, associating with poets, journalists and writers, including Aegidius Jean Blignaut. Needing a break, he then toured overseas for nine years, spending most of his time in London. The short stories that he wrote during this period formed the basis for another of his best-known books, Mafeking Road.
He lamented the fact that Johannesburg never respected its heritage; writing in The Standard Theatre "They will pull down the Standard Theatre like they have pulled down all the old buildings, theatres, gin-palaces, dosshouses, temples, shops, arcades, cafes and joints that were intimately associated with the mining-camp days of Johannesburg. Because I know Johannesburg. And I am satisfied that there is no other city in the world that is so anxious to shake off the memories of its early origins."
He married Ella Manson, and the couple were renowned for their bohemian lifestyle and parties. His parties ended well after midnight with much witty conversation. After a housewarming party he was taken ill with severe chest pains and was taken to Edenvale Hospital. On admission he was asked, "Place of birth?" He replied, "Born Kuilsrivier - Died Edenvale Hospital." He was discharged and collapsed at home a few hours later. He died as he was being rushed to hospital. He is buried in Westpark Cemetery in Westdene, with a triangular headstone that reads "Die Skrywer, The Writer, Herman Charles Bosman, b 3.2.1905, d 14.10.1951 ."
After his death, the rights to his works were auctioned, and purchased by his last wife. Upon her death, those rights were passed to her son, who retains those rights.
Only three of his books were published during his lifetime; Mafeking Road published by Dassie, and Jacaranda in the Night and Cold Stone Jug published by APB.
His biography was written several times by Valerie Rosenberg. The first was called Sunflower to the sun ISBN 0-7981-1228-X (Human & Rousseau, 1976), followed by Herman Charles Bosman, a Pictorial Biography ISBN 0-628-02148-8 (Perskor, 1981) and most recently by Herman Charles Bosman: Between the Lines ISBN 1-77007-163-6 (Struik, 2005). The last of these contains much new research and deals in detail with aspects of Bosman's life and parentage that in the first were considered to be taboo.
Because many of his stories were originally published in long-forgotten magazines and journals, there are a number of anthologies by different collators each containing a different selection. His original books have also been published many times by different publishers, although only in South Africa.