The earliest surviving text of a Robin Hood ballad is the 15th century "Robin Hood and the Monk". This is preserved in Cambridge University manuscript Ff.5.48. Written after 1450, it contains many of the elements still associated with the legend, from the Nottingham setting to the bitter enmity between Robin and the local sheriff.
The first printed version is A Gest of Robyn Hode (c. 1500), a collection of separate stories that attempts to unite the episodes into a single continuous narrative. After this comes "Robin Hood and the Potter", contained in a manuscript of c. 1503. "The Potter" is markedly different in tone from "The Monk": whereas the earlier tale is 'a thriller' the latter is more comic, its plot involving trickery and cunning rather than straightforward force.
Other early texts are dramatic pieces, the earliest being the fragmentary Robyn Hod and the Shryff off Notyngham (c. 1475). These are particularly noteworthy as they show Robin's integration into May Day rituals towards the end of the Middle Ages; Robyn Hod and the Shryff off Notyngham, among other points of interest, contains the earliest reference to Friar Tuck.
The plots of neither "the Monk" nor "the Potter" are included in the Gest; and neither is the plot of "Robin Hood and Guy of Gisborne", which is probably at least as old as those two ballads although preserved in a more recent copy. Each of these three ballads survived in a single copy, so it is unclear how much of the medieval legend has survived, and what has survived may not be typical of the medieval legend. It has been argued that the fact that the surviving ballads were preserved in written form in itself makes it unlikely they were typical; in particular, stories with an interest for the gentry were by this view more likely to be preserved. The story of Robin's aid to the 'poor knight' that takes up much of the Gest may be an example.
The character of Robin in these first texts is rougher edged than in his later incarnations. In "Robin Hood and the Monk", for example, he is shown as quick tempered and violent, assaulting Little John for defeating him in an archery contest; in the same ballad Much the Miller's Son casually kills a 'little page' in the course of rescuing Robin Hood from prison. No extant ballad early actually shows Robin Hood 'giving to the poor', although in a "A Gest of Robyn Hode" Robin does make a large loan to an unfortunate knight, which he does not in the end require to be repaid; and later in the same ballad Robin Hood states his intention of giving money to the next traveller to come down the road if he happens to be poor.
- Of my good he shall haue some,
- Yf he be a por man.
As it happens the next traveller is not poor, but it seems in context that Robin Hood is stating a general policy. The first explicit statement to the effect that Robin Hood habitually robbed from the rich to give the poor can be found in John Stow's Annales of England (1592), about a century after the publication of the Gest. But from the beginning Robin Hood is on the side of the poor; the Gest quotes Robin Hood as instructing his men that when they rob:
- loke ye do no husbonde harme
- That tilleth with his ploughe.
- No more ye shall no gode yeman
- That walketh by gren-wode shawe;
- Ne no knyght ne no squyer
- That wol be a gode felawe.
And in its final lines the Gest sums up:
- he was a good outlawe,
- And dyde pore men moch god.
Within Robin Hood's band, medieval forms of courtesy rather than modern ideals of equality are generally in evidence. In the early ballad, Robin's men usually kneel before him in strict obedience: in A Gest of Robyn Hode the king even observes that 'His men are more at his byddynge/Then my men be at myn.' Their social status, as yeomen, is shown by their weapons; they use swords rather than quarterstaffs. The only character to use a quarterstaff in the early ballads is the potter, and Robin Hood does not take to a staff until the 17th century Robin Hood and Little John.
The political and social assumptions underlying the early Robin Hood ballads have long been controversial. It has been influentially argued by J. C. Holt that the Robin Hood legend was cultivated in the households of the gentry, and that it would be mistaken to see in him a figure of peasant revolt. He is not a peasant but a yeoman, and his tales make no mention of the complaints of the peasants, such as oppressive taxes. He appears not so much as a revolt against societal standards as an embodiment of them, being generous, pious, and courteous, opposed to stingy, worldly, and churlish foes. Other scholars have by contrast stressed the subversive aspects of the legend, and see in the medieval Robin Hood ballads a plebeian literature hostile to the feudal order.