Recorded in several forms, this is one of a group of English medieval surnames which include the prefix 'Little'. These include the modern spellings as Littleboy, Littlechild, Littlefair, Littlejohn, Littlepage, and Littleproud, and all use the prefix as a nickname of endearment. It has been said that as Littlejohn, also spelt Litteljohn and Littlejohns, the meaning may refer to a very large, tall, person, as in the case of Little John, the second in command to the band of outlaws lead by Robin Hood. There the reference is clearly sardonic for a large man. With Littleproud there seems to be a sarcastic element, since the name literally means 'No value'. Even with medievval robust humour, it is difficult to believe that this was the original meaning. Fifteen percent of all surnames from the medieval period, when surnames were first created, are essentially nicknames, and these surnames are good examples of the genre. Early examples of recordings taken from the surviving rolls and registers of the Middle Ages include: Robert Littelboie in the Friary Rolls of Leicester in the year 1206, Ralph Litechild in the Pipe Rolls of Leicester in 1209, Agnes Lutfair of Stafford in 1381, Litel jon of Colchester in 1350, and Matilda Lytellprowd in the Poll Tax rolls of Yorkshire in 1379.

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