VH is born on 5 October into a bourgeois family active in the public life of the First Czechoslovak Republic. His father Václav Maria Havel (1897–1979) was an entrepreneur in the construction industry: his projects included the Barrandov Terraces and the Barrandov residential area. His grandfather Vácslav Havel (1861–1921) built the Lucerna Palace in Prague. His uncle Miloš Havel (1899–1968) founded the AB Film Works in Barrandov and was a leading Czech film producer in the 1930s. His mother Božena Havlová (1913–1970) was interested in fine arts. She was the daughter of diplomat Hugo Vavrečka (1880–1952), who published under the pseudonym Hugo Vavris.
Brother Ivan M. Havel, a future computer scientist and philosopher, is born.
During WWII the family were based outside Prague, mainly at their country residence at Havlov in South Moravia and in Zlín.
Following the communist putsch, the family is persecuted, their property is confiscated and individual members are prosecuted. Uncle Miloš emigrates. Václav and Ivan Havel are barred from studying for class background reasons. Václav does an apprenticeship as a chemistry lab assistant (1953) and passes does his school leaving exams by correspondence while employed (1954).
VH acquires his first literary and critical experience in the company of his peers, who call themselves the 36ers (Šestatřicátníci). Members include future key figures in Czech literature in the second half of the 20th century, among them Jiří Kuběna, Josef Topol, Věra Linhartová, Viola Fischerová, Jan Zábrana and others. He gradually establishes contact with other groups and individuals active in the “alternative" culture (Jiří Kolář, Vladimír Holan, Jaroslav Seifert and others) not supported by the communist regime. VH composes four manuscript collections of poetry and writes literary reflections and critiques.
Begins publishing texts about literature and film. Makes his first public appearance at a meeting of young authors at Dobříš (1956), where he delivers a critically toned paper. Following a number of unsuccessful attempts to enrol in the humanities he studies at the economics faculty of the Czech Technical University in Prague. He makes his first attempt to enter the FAMU film school but is rejected.
Havel enters two-year basic military service.
Together with fellow soldier Karel Brynda, he writes, half for fun, the play Life Ahead, set in a military context. Engaging in the creative cultural life of the “Socialist Youth Movement" and taking part in competitions proves more pleasant than training. At the end of his service he applies to the Academy of Performing Arts and is again rejected. He is accepted to do correspondence studies in 1962.