The name "Tripping Billies" came to be when a band member's girlfriend told Dave Matthews that his band sounded like "a bunch of hillbillies tripping on acid". The band thought this was hilarious and named this song after it.
Matthews talked about the origins of this song at the show that was recorded for VH1 Storytellers on March 24, 1999. This part of the show, however, was not part of the aired program but can be heard on the fan traded tape of the show. He said that the "Dragons were smoked" line is a reference to "Puff, the Magic Dragon". He also mentioned taking some LSD on a beach in South Africa with Julia Grey and some friends. Then shortly thereafter deciding that he did not want to trip. "I was looking at my girlfriend Julia's face and then it melted into my mother's! And I thought, 'oh, no, that's not good.'"