Riddling quickens the mind and lifts the spirit. It is an ancient and universal art which uses devices such as pun, double-entendre and metaphor to engage with the world in a sort of intellectual game-playing. Some ninety-five riddles in OE, all of them poems, are preserved in the Exeter Book, the exact number varying according to how editors divide them. They are copied in three groups, with other poems intervening, and some of the latter (such as Wulf and Eadwacer, Text 39) are themselves so enigmatic that critics have been tempted to include them in the riddling genre as well. It is likely that the OE riddles had a variety of different authors. They drew on a strong Latin tradition associated especially with Symphosius, whose collection of three-line ænigmata, compiled in the fourth century or the fifth, was enormously popular. In England, the early eighth-century bishop of Sherborne, Aldhelm, composed one hundred ænigmata in order to illustrate his study of Latin metre. (He composed OE verse as well, but none, as far as we can tell, survives.) In the eighth century, a collection of one hundred Latin riddles was put together by Tatwine, archbishop of Canterbury, and a writer calling himself ‘Eusebius’, who was possibly Bede's friend Hwætberht, abbot of Jarrow.

Though strongly influenced by such Latin precedents, the OE riddles, with a few exceptions, are not simply translations. In general they are longer than the Latin riddles and contain more detail, and they are far more playful in style.