Castlemilk was one of the 'big four' housing estates built by Glasgow City Council in the 1950s. In 1937, the Stuarts of Castlemilk, owners of the land, sold off their land to the Corporation. Work began on the tenement housing scheme in 1953 with the first tenants moving in 1955. The scheme was planned to accomodate around 40,000 people from the slums of inner city Glasgow. During the 1960s, 9 tower blocks were added to the scheme at three locations:

However, the scheme was ill-planned and Castlemilk, like similar schemes, Drumchapel and Easterhouse became a wasteland of poverty and deprivation. Yes, there were better houses than the slums that the people had known in the inner city. But there were no amenities and rather than a united community spirit, there were the remnants of a multitude of many fractured communities broken up by the slum clearances. Castlemilk began it's own slum clearances out of necessity in the 1990s. The area was found to be the most deprived in Scotland and something had to be done. Tenements were knocked down and replaced with more family friendly homes and the Mitchellhill flats that spawned "The Jeely Piece Song" were demolished in 2005 along with 30 Bogany Terrace in the mid 1990s. The area was found to be the second most deprived area in Scotland in 2006, behind Ferguslie Park in Paisley.

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