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It was a largely rural area with only a handful of residential properties until the 1930s, when a transformation began that left the area almost unrecognisable over the next 30 years. A large number of private houses, some of which were the among the most desirable in Central England, were developed during this time. They are still expensive and highly sought after today.
"Big Bertha", an anti-aircraft gun, was erected at the top of the hill near City Road when World War II broke out in 1939. Although this gun proved useful in eliminating enemy aircraft, it also became an enemy target. A landmine was dropped within a few hundred yards of the gun on 19 November 1940, demolishing four houses in City Road and severely damaging several others, resulting in the deaths of 10 people and injuring many more. On 21 December 1940, a stray shell from the anti-aircraft gun fell down the chimney of the Boat Inn one mile away in Dudley Road East, Tividale, resulting in 13 deaths and dozens of injuries. On 12 August 1941, the Luftwaffe dropped a landmine several hundreds yards from the gun in Birch Crescent, demolishing a pair of new semi-detached houses and severely damaging several others, leaving four people dead and several others injured. The gun was dismantled after the war ended in 1945, but several traces of it remain more than 70 years later.
Oakham's most famous resident was George Smith, known as the Dudley Hangman. He was born in nearby Rowley Regis in 1805. In 1840 he became assistant to the executioner William Calcraft before being appointed as executioner for Staffordshire in his own right. He became notorious for entertaining customers in Black Country pubs with gruesome stories of his work. There was a pub in Oakham, now demolished, called the 'Hangman's Tree' which was named in George Smith's honour. It was built in the 1930s but demolished in 2007.
Oakham Primary School has served the Sandwell section of Oakham since 1939, and now has 420 places for pupils aged 5–11 as well as a nursery unit for a total of 60 children aged 3 or 4 years. Grace Mary Primary is another primary school in the area, having opened in April 1959.