Lyric discussion by douglondon 

Some good interpretations of the song, and some slightly erroneous due to less knowledge of British/ Irish history.

Firstly, the title. The term "Oliver's Army" is a reference to the history of British occupation of Ireland, starting with Cromwell. Cromwell's New Model Army was also the first professional army and drew soldiers from the working class.

The song is about British imperialism, and the British army recruiting working class young men to occupy foreign territories.

The first verse is about recruitment to the Army - young men in big cities were often advised by careers/ unemployment offices to join the army as a way out of unemployment. As someone else pointed out, the line 'Have you got yourself an occupation' could equally apply to potential recruits to the British army, and to the citizens of lands they occupied.

The second verse references the fact that young men were thrown into the front line, and were often scared and jumpy. As a result, they were prone to 'itchy triggers'. As other posters point out, Checkpoint Charlie was a famous crossing point of the Berlin Wall: In this case, however, I would assume that Costello uses the term to refer to a soldier manning a checkpoint. The phrase 'white nigger' is an extremely racist term for the Irish. The connotations are clear.

The last verse then expands the song to talk about the history of (British) imperialism, rather than simply Ireland. It includes references to Hong Kong, the British Mandate for Palestine, South Africa, and Korea. It also reinforces the message of unemployed men from working class cities (Newcastle, Liverpool and London) being advised to join the army. The reference to Churchill is because, as much as he's primarily remembered as a great war time leader, he also held some pretty unsavoury views. He was known to be an advocate of British imperialism and saw other races as 'uncivilized.' He was responsible, among other things, for the dispatch of British soldiers to put down the Mau Mau rebellion.

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