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Originally, this expression had a negative connotation: a person who moves frequently pays a price by not having roots in any specific place, and is probably a wastrel. In modern parlance, the expression is still used for somebody who moves frequently and thus is perceived as avoiding responsibilities and cares but with less presumption that they are good-for-nothing.
The expression is generally atributed to Publilius Syrus, who was born in Syria around 85 BC and was brought to Italy as a slave, where his wit and talent won him the favor of his master who freed and educated him. Today, he is remembered for his moral sayings (known as sententiae in Latin), but in his time he was likely best known as a talented mime and improviser.
The expression was in use in English in the 16th century as it makes an appearance in John Heywood's A Dialogue conteinyng the nomber in effect of all the Prouerbes in the Englishe tongue: the rollyng stone neuer gatherth mosse. Heywood was an English dramatist employed at the courts of Henry VIII and his daughter Mary I, but when Elizabeth I came to the throne in 1564, Heywood (a Roman Catholic) was forced to flee to the continent. He was important in the development of English comedy, specifically short comic dialogues known as interludes - but is now best remembered for his book of proverbs.
The negative interpretation of the expression is clear in Randle Cotgrave's 1611 A dictionarie of the French and English tongues, which defines the French word "rodeur" as "a vagabond, roamer, wanderer, street-walker, highway-beater; a rolling stone, one that does nought but runne here and there, trot up and downe, rogue all the country over."
In the 1950s, Muddy Waters released "Rollin Stone" which included the verse:
Well, my mother told my father
Just before I was born,
"I got a boy child's comin',
Gonna be a rollin' stone
According to musician Brian Jones, back in 1962, when he was booking a gig for the blues band he'd recently formed with Mick Jagger and Keith Richards, he was asked by the club's owner for the name of his group. Casting around for an answer, his eyes landed on an album by his beloved Muddy Waters including "Rollin Stone," and the rest, as they say, is history.
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