The Finkler Question by Howard Jacobson is a book I would recommend: it is sprinkled with comic one liners and ironic contradictions that echo the surreal and illogical grammatical structure of Catch 22, but at the same time it is a long and sad meditation on the nature of life and love, death and grief, family and identity.
The story, if indeed there is one, tells of three men, two Jewish, and one who aspires to Jewishness. Their lives share moments of tenderness and betrayal. The novel explores their relationships with each other and their families. For Julian Treslove life is a series of failed and inadequate relationships: love can only be consummated in death, like the climax of an opera. No real woman can match his vision. Perhaps if he were Jewish it would be different? Sam Finkler, being Jewish, is in a state of rebellion and shame about the excesses of Zionism; he marries out, is unfaithful. Libor Sevcik mourns the death of his wife.
There are many Jewish issues and preoccupations – the growth of anti-semitism, the impact of Zionism on the perception of Jews – but the characters and the feelings explored are universal too. It will make you laugh out loud – but beware – there is a deep well of sadness and unfulfillment at the heart of this story.