Baba Brinkman is a rapping Medievalist (wow, we have never typed those words) who hails from Canada. He possesses mad rhymes, as well as a master's degree in Medieval and Renaissance English literature (his thesis pointed out the parallels between hip hop and literary poetry). He has toured the globe with his one-man show "Rap Canterbury Tales." Word.
You read that right. In 1969, a rock musical about Chaucer's rascally pilgrims played on Broadway. The lyrics are cringe-worthy at times, but the musical's cheerful sauciness will eventually win you over. Ask your teacher for extra credit points if you agree to sing the songs in class.
Gather round for ye olde drinking songs. Pubs like the one owned by Host Harry Bailly in The Canterbury Tales were popular gathering spots in medieval England (and present-day England too, come to think of it). After a few draughts of ale, rosy-cheeked men would start to sing. This is an album of popular drinking songs.
The Early Music Show is a recurring program on BBC 3 Radio. They have dedicated several episodes to Chaucer and the music from his era. Their playlist gives you a sense of the musical tastes of his era.
This great, online Medieval resource has a whole section on Middle English music. You can listen to audio snippets of Medieval music and read the lyrics in Middle English. You'll be a star at parties when you break out hits like "Fowles in the Frith": "Fowles in the frith,/ The fisshes in the flood,/ And I mon waxe wood/ Much sorwe I walke with/ For beste of boon and blood." Sing along!