Cleaver started Ass Ponys in 1988, and they released their first album two years later. During this time, he lived in Bethel. With regard to why Ass Ponys broke up, Cleaver says, “I just kind of felt that Ass Ponys had run its course,” and “We were coming up with new material, but I just really wasn’t all that interested in it anymore.” After he met Lisa Walker in 2001, around the time Ass Ponys released their last album of original material, Lohio, they decided to form a band, which Cleaver decided to call “Wussy” because “I just like the way it looks on a T-shirt. It’s another one of my names ensured not to get anywhere.” In an interview with the Portland Mercury, Cleaver said that he originally enlisted Walker to sing with him when he was asked to perform solo for a Cincinnati awards show. He has been called one of the best singer-songwriters in America by Freedy Johnston.