Recorded in several spellings including Baillie, Bailey, Bailess, Bailiss, Baylis, Bayless and others, this is a medieval Anglo-Scottish surname, although one of French origins. Introduced into England at the famous conquest of England in 1066, it was originally occupational for an official within a royal or noble household. It derives from the word "baillis" and the later English 'bailliff', meaning an officer of the civil court who issues and serves writs, whilst in Scotland the word survives as 'bailie'. This is the title of a chief magistrate for a county or barony. The surname was first recorded in England in the 13th century, and early examples include Henry Bailey of Oxford in the Hundred Rolls of landowners in 1273, Richard le Bailif of Hereford in the same year, William de Bailli of Lothian, Scotland, in 1315, and Samuel Baylles in the register of the Freemen of the City of York in 1535. Other examples include that on August 13th 1750 of John Bayliss who married Sarah Mitchell at St. George's Mayfair, Westminster, whlst Ann Bayless was christened on February 5th 1759 at St. Sepulchre church, in the city of London. The first recorded spelling of the family name is probably that of Roger le Baillie of the county of Somerset, in the register known as Kirby's Quest for the year 1272. Surnames became necessary when governments introduced personal taxation. In England this was known as Poll Tax. Throughout the centuries, surnames in every country have continued to "develop" often leading to astonishing variants of the original spelling.

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