The song contains numerous Shakespeare references including Juliet from Romeo and Juliet, Malvolio from Twelfth Night and the phrase "To be, or not to be" from Hamlet, which is changed to "To skip or not to skip, that is the question".

Sweetnam thought that the title "Billy Shakespeare" was too long, and decided to shorten it.

The music video for "Billy S.", filmed in Southern California, features Skye Sweetnam recording herself singing into a handheld camera.

Skye is also shown, while making her video, gathering a group of people for the purpose of throwing a party and ultimately skipping school, walking triumphantly past the (school) bus.

The video for "Billy S." received regular airplay on MuchMusic and YTV.