- Son of Denis Leary and Ann Leary.
- Despite having been born in Britain, was not automatically granted British citizenship. This was due to a combination of the emergency situation surrounding his birth and then-recent law changes there due to illegal immigration problems. Before the latter happened, any baby born in Britain was automatically a British citizen.
- Was born 3 months premature in London when his mother's water unexpectedly broke shortly after arrival during what was supposed to be a weekend trip to England for his father, Denis Leary, to perform on a comedy show.
- Brother of Devin Leary.
- His father is a distant cousin of Conan O'Brien and Jane O'Brien.
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