Bosman was born at Kuils River, near Cape Town, to an Afrikaner family. 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. While there he contributed to the school magazine. When Bosman was sixteen, he started writing short stories for the national Sunday newspaper (the Sunday Times). He attended the Johannesburg College of Education (which in 2002 was incorporated into the University of the Witwatersrand) and submitted various pieces to student literary competitions.
After graduation, Bosman accepted a teaching position in the Groot Marico district in an Afrikaans-language school. The area provided the backdrop for his best-known short stories, the Oom Schalk Lourens series (featuring an older character named Oom Schalk Lourens) and the Voorkamer sketches.
Over the school holidays in 1926, Bosman visited his family in Johannesburg. During an argument, he shot and killed his stepbrother. Bosman was sentenced to death for the crime and was sent to Death row at the Pretoria Central Prison. His sentence was later reduced to ten years with hard labour. In 1930, he was released on parole after serving half his sentence. His prison experiences formed the basis for his semi-autobiographical book, Cold Stone Jug.
Bosman 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. He 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.
At the start of the Second World War, he returned to South Africa and worked as a journalist. During this time he translated the Rubaiyat of Omar Khayyam into Afrikaans.
Bosman lamented the fact that Johannesburg neglected its heritage. In The Standard Theatre he complained that the city's residents:
"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."
Bosman's second wife was Ella Manson. The couple were renowned for their bohemian lifestyle and parties, which featured witty conversation and usually ended well after midnight.
From 1948 to his death in 1951, Bosman was employed as proof editor at The Sunday Express. In addition, he was contracted to write a weekly Voorkamer story for The Forum magazine.
His last wife was Helena Lake (née Stegmann). After a housewarming party in October 1951, Bosman experienced severe chest pains and was taken to Edenvale Hospital. On admission, he was asked for his birthplace. He replied, "Born Kuilsrivier – Died Edenvale Hospital." He was discharged and collapsed at home a few hours later. Bosman died as he was being rushed to hospital. He is buried in Westpark Cemetery in Westdene under 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. They were purchased by his last wife, Helena, and upon her death, the rights were passed to her son, who retains them. In 1960, however, Helena sold some of his documents and 123 of his water colours and pencil sketches to the Harry Ransom Center in Texas.
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. Mafeking Road has never been out of print since its publication in 1947.
His biography was written several times by Valerie Rosenberg. Her first effort was called Sunflower to the Sun, followed by Herman Charles Bosman, a Pictorial Biography, and most recently by Herman Charles Bosman: Between the Lines. The last of these contains much new research and deals in detail with aspects of Bosman's life and parentage that were previously considered 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.
The Herman Charles Bosman Literary Society meets annually for readings, performances and discussions of his works.Some of the ISBNs and publishers below may not be for the original edition.
Mafeking Road & Other Stories (1947), ISBN 0-7981-3902-1 Human & Rousseau, ISBN 978-0-9793330-6-4 Archipelago Books (2008)
Rubaijat van Omar Khajjam (1948), Colin Reed-McDonald
Cold Stone Jug (1949), ISBN 0-7981-3981-1 Human & Rousseau
Veld-trails and Pavements (1949), with Carel Bredell, Afrikaanse Pers-Boekhandel
Cask of Jerepigo (1957), Central News Agency
Unto Dust (1963), edited by Lionel Abrahams, ISBN 0-7981-1501-7 Anthony Blond
Bosman at his Best: a choice of stories and sketches (1965) edited by Lionel Abrahams ISBN 0-7981-0249-7 Human & Rousseau
Bosman's Johannesburg (1986) edited by Stephen Gray ISBN 0-7981-2001-0 Human & Rousseau
Ramoutsa Road (1987) ISBN 0-86852-130-2 Ad. Donker
A Bekkersdal Marathon (1971), ISBN 0-7981-0030-3 Human & Rousseau
The Earth is Waiting (1974)
Willemsdorp (1977), ISBN 0-7981-3901-3 Human & Rousseau
Almost Forgotten Stories (1979) ISBN 0-86978-167-7 H. Timmins
My Friend Herman Charles Bosman  Perskor. author: Aegidius Jean Blignaut
Dead End Road  AD.Donker. author: Aegidius Jean Blignaut
Selected Stories (1980), edited by Stephen Gray, ISBN 0-7981-1031-7 Human & Rousseau
The Collected Works of Herman Charles Bosman (1981), edited by Lionel Abrahams, ISBN 0-86850-029-1 Jonathan Ball
The Bosman I like (1981), edited by Patrick Mynhardt, ISBN 0-7981-1179-8 Human & Rousseau
Death Hath Eloquence (1981), edited by Aegidius Jean Blignaut, ISBN 0-86984-189-0 Christelike Uitgewersmaatskappy
Uncollected Essays (1981), ISBN 0-86978-167-7 Timmins
The Illustrated Bosman (1985), ISBN 0-86850-112-3 Jonathan Ball
Makapan's Cave and other stories (1987), edited by Stephen Gray, ISBN 0-14-009262-5 Penguin Books.
A Bosman Treasury (1991), edited by Ian Lusted, ISBN 0-7981-2830-5 Human & Rousseau
Jurie Steyn's Post Office (1991), ISBN 0-7981-2903-4 Human & Rousseau
Herman Charles Bosman : the prose juvenilia (1998), collected and introduced by M. C. Andersen, ISBN 1-86888-049-4 University of South Africa
Idle Talk : voorkamer stories (1999), edited by Craig MacKenzie, ISBN 0-7981-3982-X Human & Rousseau
Old Transvaal Stories (2000), edited by Craig MacKenzie, ISBN 0-7981-4085-2 Human & Rousseau
The Rooinek and Other Boer War Stories (2000), edited by Craig MacKenzie, ISBN 0-7981-4031-3 Human & Rousseau
Jacaranda in the Night (2000), ISBN 0-7981-4084-4 Human & Rousseau
Best of Bosman (2001), edited by Stephen Gray and Craig MacKenzie, ISBN 0-7981-4203-0 Human & Rousseau
Seed-Time and Harvest, and Other Stories (2001), edited by Craig MacKenzie, ISBN 0-7981-4186-7 Human & Rousseau
Verborge Skatte: Herman Charles Bosman in/on Afrikaans (2001), collected by Leon de Kock, ISBN 0-7981-4185-9 Human & Rousseau
Cold Stone Jug (1982) adapted by Barney Simon from the play by Stephen Gray ISBN 0-7981-1309-X Human & Rousseau