The Song of Roland is the most famous of the "chansons de geste" (songs of deeds) of the Middle Ages. It provides a fascinating view into the spirit of warriors of that time and their motivation. The Song of Roland gives an idealized picture, of course, and if we can believe the historians, the medieval knights never lived up to their chivalric ideal.
The Song of Roland is not commonly included in the canon of must-read classics. Except in France, maybe. I assume the reason is that people in our time do not trace back their roots to the feudalism of the Middle Ages, and that they consider the chapter of chivalry closed after Cervantes's satirical portrait of knighthood in "Don Quixote". In one respect, however, this gory tale of slaughter, martyrdom and revenge is very contemporary. It illustrates the mindset of crusaders who see the world in terms of Good and Evil, and the language they use to incite contempt of the other party.
Apart from its historical value, the Song of Roland is also worth reading as literature - as an outstanding example for the heroic epic and as a piece of art whose "simple yet elevated style and tone of high moral purpose" (R. Harrison) is reminiscent of the Old Testament.
The three most easily available translations of the Song of Roland in the market are:
W.S. Merwin's 1963 prose translation with introduction, re-published in paperback by Random House's "Modern Library" in 2001 (ISBN 0375757112). His nine-page introduction is a succinct but sufficient overview of the historical events of AD 778 that became the basis of the Song of Roland. The translation stands out for its readability, and Merwin's choice of modern English makes the descriptions of violence even more direct and graphic: "And Oliver rides through the battle, with his spear shattered to a stump, charges against Malun, a pagan, breaks his gilded shield with the flowers painted on it, knocks the eyes out of his head and brings his brains tumbling down to his feet." (page 43).
Robert Harrison's 1970 translation for Penguin Book's budget line "Mentor Books" (ISBN 0451528573) captures the throbbing, urgent rhythm of the verse form best: "Olivier now gallops through the fray - / his lance has snapped, he only has a stump - / and goes to strike a pagan, Malsaron. / He breaks his gilt, fleuron-emblazoned shield, / bursting both his eyeball from his head - / his brain comes tumbling downward to his feet - " (page 93). "Fleuron-emblazoned" is quite enigmatic compared to Merwin's clear "with the flowers painted on it", but Harrison redeems himself by choosing "bursting" to emphasize the violence of the attack. The big plus of Harrison's book is his 42-page introduction. He explains the logic of medieval chivalry, why cruelty coexisted with sensitivity, and butchery with prayer. One interesting concept is the medieval "ethos of success," or in other words the idea that the outcome justifies the means: When a knight killed another knight it was the will of God that this had happened, no matter by what means. Make the opponent trip and chop off his head - see, God is on your side. Harrison goes to quite some length to introduce the instruments of war, the armor and weapons, which is very helpful since the main body of the Song of Roland is about the glory and slaughter of battle.
Glyn Burgess's 1990 translation for Penguin Classics (ISBN 0140445323) is the most recent translation of the three. He stays closest to the form of the original, which gives his translation a certain wooden inflexibility but also a not entirely unbecoming pathos. His translation of Olivier's attack on Malun is quite telling: "Oliver rides through the thick of the fray; / His lance shaft is broken, only a stump remains. / He goes to strike a pagan, Malun; / He breaks his shield, wrought with gold and flowers, / and smites both his eyes out of his head. / His brains come spilling out over his feet;" (page 72) While the use of "wrought" and "smite" sounds a bit old-fashioned, "spilling" is an excellent choice. Burgess added a 19-page introduction to his translation. It focuses mostly on the literary qualities of the Song of Roland; for the first-time reader of the Song of Roland, Harrison's introduction is more helpful. The additional value of the Penguin Classics edition lies in an Appendix with about one third of the original version of the "Chanson de Roland" - the key passages of the work in Old French.
While all three translations have their pros and cons, I tend to recommend Harrison's book over the two others. It strikes a good balance between the clarity of Merwin's prose translation and the wooden feel of Burgess's more literal verse translation. In addition, it impresses with its useful introduction and its unbeatable value for money.