Josef Škvorecký, who has died aged 87, belonged to that great generation of postwar Czech writers including Václav Havel, Bohumil Hrabal, Ludvík Vaculík, Ivan Klíma, Arnošt Lustig and Milan Kundera. Their novels, plays, essays and memoirs defined modern Czech literature and gave the rest of the world a deeper understanding of ordinary lives under German fascism and Soviet communism, the two totalitarian systems that dominated their country for much of the 20th century.

Josef wrote more than 40 books, including his masterpiece, The Engineer of Human Souls, which won the Canadian governor general's award for fiction in 1984. Set in the Czech émigré community in Toronto, the novel is narrated by Josef's alter ego, the cynical, skirt-chasing, sax-playing Danny Smirický, now a respected English professor at a Toronto university who is assailed by memories of his life and loves under fascist and communist tyrannies. As Josef's translator, what I found most difficult to convey was his unique ability to capture how different political regimes affect the way his characters speak and write.

Josef also wrote two "American" novels, Dvorák in Love (1984), about the Czech composer's sojourn in New York in the 1890s, and The Bride from Texas (1992), set during the American civil war. The core of his work is a series of seven semi-autobiographical, jazz-soaked books, all but one of them narrated by Smirický. The series begins with The Cowards, which Josef wrote when he was 24, and ends with Ordinary Lives, written in 2004 and published in English in 2008. The exception is Republic of Whores, a hilarious, third-person account of Smirický's stint in a Czech tank battalion in the 1950s. These books – along with a series of crime novels featuring the melancholic homicide detective Lieutenant Boruvka – can be read as a single, vast epic covering the most crucial and painful periods of modern Czech history, but anchored in the magically remembered town of his youth.

Josef's lifetime spanned several radically different eras. He was born in Náchod, in north-eastern Bohemia, into the liberal democracy of the first Czechoslovak republic. He grew up in Nazi-occupied Bohemia, began writing in the era of Stalinism after 1948, then consolidated his reputation as a courageous, entertaining and often controversial novelist and screenwriter in Prague during the slow thaw of the late 1950s and 60s. After the Soviet invasion crushed the Prague Spring in 1968, he and his wife, Zdena Salivarová, whom he had married in 1958, emigrated to Canada, where he taught literature and film studies at the University of Toronto. The creative freedom he found in the west gave him a new lease of life.

He and his wife established a Czech-language publishing house, 68 Publishers, named after the year that Josef liked to describe as the "annus mirabilis, annus horribilis" of Czech history. Over the next two decades, with Josef as her chief in-house editor, and often on the edge of bankruptcy, Zdena published work by scores of banned Czech and Slovak writers, including Josef himself, Kundera, Havel and the Nobel prize-winning poet Jaroslav Seifert. They marketed the books to Czech readers around the world, and arranged for them to be smuggled into Czechoslovakia, where the books were circulated from hand to hand. I can recall the illicit thrill of reading a contraband copy of his 1972 novel The Miracle Game in Czechoslovakia in a "salad edition", so-called because the book had passed through so many hands the pages had come loose.

Josef was immensely prolific, with 10 collections of short stories, two novellas (the best known of which is The Bass Saxophone) and a dozen collections of essays on politics, literature and cinema to his credit. He was also a master translator, rendering works by Hemingway and Faulkner into Czech. He was a prodigious and generous correspondent, and undoubtedly we will yet see collections of his letters published posthumously.

In 1990, Havel, then the new Czechoslovak president, awarded Josef and Zdena the county's highest honour, the Order of the White Lion. Josef was nominated for the Nobel prize in 1982, inducted into the Order of Canada in 1992, and made a chevalier of the Ordre des Arts et des Lettres in 1996. He had the good fortune to be genuinely popular in his lifetime, respected by literary critics and adored by readers from all backgrounds and many different countries (his works have been translated into at least 20 languages). A private academy in Prague is named after him, and he lived to see many of his stories made into popular movies and television series.

One of my fondest memories of him is a conference held in Náchod in 2004 to celebrate his 80th birthday. Dozens of scholars and translators from all over the world converged on the small town to discuss his work. The highlight was a literary tour of the area, and as the guide walked us through Náchod, pointing out places where Josef had set crucial scenes from his novels, I realised for the first time how thin was the line between his reality and his fiction, and how deeply he had written himself into the life of his country.

The last stop on the tour was a pub called The Port Arthur, where the jazz band Josef had played for in his youth, Red Music, had often performed, and which was one of the locales in his early and most controversial novel, The Cowards. While a youthful jazz trio struck up a swing classic, Josef and Zdena sat at a table surrounded by a group of friends whom he introduced to us as the real-life models for some of the characters in his books. It was a deeply moving encounter: they, like their author, had grown old but would live on through his stories.

Zdena survives him.

• Josef Václav Škvorecký, writer, born 27 September 1924; died 3 January 2012