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Hickey was born in St. Albans Street, Pall Mall, Westminster, on the 30th June 1749, the seventh son of Joseph Hickey, a successful Irish Solicitor, and Mary Boulton, from a Yorkshire gentry family. He began his education at Westminster School, but was removed "in high disgrace" in December 1763 after neglecting his studies, frequenting public houses and leading, in his words, a life of "idleness and dissipation". Instead he was sent to a private school at Streatham in Surrey, where he was able to study Arithmetic, Writing, French, Drawing and Dancing in addition to the Classical Studies which had failed to engage him at Westminster. In January 1766 he left school and began his legal training, but he continued to lead an extremely debauched existence. In his old age Hickey wrote rather censoriously of his youthful indiscretions in London, where he lived well beyond his means, drinking and gambling heavily, playing at billiards and at cricket, and keeping a mistress called Nanny Harris, to whom he was very attached, in rooms in Berwick Street. Eventually he embezzled £500 (a considerable sum for those days) from the accounts in his father's office, and when this was discovered it was resolved to send the prodigal to India to see if he could make good. Accordingly Hickey embarked on the Plassey, a fast Indiaman, at Dungeness on the 4th January 1769.