In the year 778 Charlemagne (Charles the Great), who at the time was already King of the Franks and King of the Lombards but was not yet Emperor (which he will become in 800), crossed the Pyrenees. He had been invited by the Muslim governors of a few Spanish cities. Those governors were rebelling against the Emir of Córdoba, and they wanted Charlemagne's help. In exchange for his help they offered him, if victorious, the control of the Marca Hispánica, which included parts of Catalonia, Aragon and Navarre.
Things didn't quite work out. Charlemagne besieged Zaragoza for several months without making any progress, and was losing confidence. News, back home, of a revolt by the Saxons, gave Charlemagne an excuse to get the hell out of Spain without losing too much face. (It's also possible that the Emir of Córdoba offered him gold for him to fuck off, as some historians have suggested.)
On its way back to France, Charlemagne's army sacked Pamplona (as you do). That didn't go down very well with the locals, understandably. While crossing the Pyrenees, at the pass of Roncesvalles (or Roncevaux), the Frankish army was ambushed by the Basques, in retaliation for Pamplona. (The Basques are many things, but they're certainly not pushovers.) The Basques attacked and destroyed the Franks' rearguard, leaving hundreds of people dead. Among the dead was a relatively unknown Frankish knight called Roland.
Three hundred years later, around the year 1100, appears in France La Chanson de Roland (The Song of Roland), an epic poem that told (taking huge liberties with the historical facts) the story of Charlemagne's Spanish campaign and the battle of Roncesvalles. The poem seems to have been written by a certain Turold. Most likely this Turold simply put down on paper a story that had been circulating orally for quite some time, a story that was part of what was known as the Carolingian Cycle.
In medieval times, itinerant minstrels and troubadours would travel from square to square, and from court to court, telling stories, stories that they were free to change, enrich and embellish as they wished. Those stories were roughly divided into three groups:
1. The Matter of France (or Carolingian Cycle), which revolved around the history of the French kings
2. The Matter of Britain (or Arthurian Cycle), which revolved around the legends associated with King Arthur
3. The Matter of Rome, which revolved around Greek and Roman myths and legends
La Chanson de Roland travelled across Europe. Roland became Roldán in Spain and Orlando in Italy, for some reason. (Why Orlando and not simply Rolando? I don't know.)
Let's fast forward a few centuries. In 1495, an Italian poet called Matteo Maria Boiardo published an epic poem called Orlando Innamorato (Orlando in Love), a fairly average work which not many people nowadays feel like reading. In this poem Boiardo decided to combine elements of the Carolingian Cycle with elements of the Arthurian Cycle. (A bit like mixing Star Trek with Star Wars, something that would probably enrage fans of either.) Boiardo left the poem unfinished. (Maybe even he got bored with it.)
A few decades later, another Italian poet, Ludovico Ariosto, decided to continue the Orlando Innamorato, picking up from where Boiardo had left off. (There was no concept of copyright in those days, you could do whatever you wanted.) In 1532 Ariosto published the final version of his Orlando Furioso (sometimes translated in English as The Frenzy of Orlando rather than Furious Orlando or Raging Orlando.)
Ariosto went one step further than Boiardo, adding the Matter of Rome to the Matter of France and the Matter of Britain. A real hodgepodge. You find Greek gods next to Merlin and dragons next to Frankish and Moorish knights. (There's even some proto-science-fiction. At one point Orlando travels to the moon.) It sounds like a real mess, but Ariosto made it work. While no one reads the Orlando Innamorato anymore, Orlando Furioso is considered a timeless classic.
The Orlando Furioso is one of the last epic poems. (Portugal's national poem The Lusiads being another.) European literature was about to change forever. Let's compare the Orlando Furioso with two works that were about to be written just a few decades later: Shakespeare's plays and Cervantes' Don Quixote. Ariosto's poem doesn't have the psychological depth found in Shakespeare (the characters in the Orlando Furioso are quite two-dimensional), nor does it have the irony and the satire that you find in Don Quixote, considered by many to be the very first modern novel.
Nevertheless the Orlando Furioso is engaging and fun to read. It's pure escapism. The French philosopher Voltaire, the Scottish novelist Walter Scott, and the English poet Lord Byron, all thought that the Orlando Furioso was superior to Homer's epic poems the Iliad and the Odyssey, both. That's a pretty bold statement. (Well, the Odyssey is wonderful, but the Iliad is a bit of a drag, though not many people like to admit it. It's one duel after another, all pretty much identical.)
Many people are put off from reading the Orlando Furioso for two reasons. The first one is its length. The Orlando Furioso is huge. It's three times the length of the Odyssey, in itself a fairly big book. The second one is that, being a continuation of the Orlando Innamorato, reading the Orlando Furioso on its own is a bit like watching a movie halfway, without knowing what happened earlier. But you just need to read a brief synopsis of the Orlando Innamorato to bring you up to speed. That's what most people do.
I haven't read the poem yet, though I'd like to read it some day. (Whether I'll find the time remains to be seen.) At the moment, like most Italians, the extent of my knowledge is confined to the first two lines, which I copied here together with Guido Waldman's English translation for Oxford University Press:
Le donne, i cavallier, l’arme, gli amori,
le cortesie, l’audaci imprese io canto
I sing of knights and ladies, of love and arms,
of courtly chivalry, of courageous deeds
