crockett played music on the streets in the french quarter of new orleans and in deep ellum, dallas as a teenager. later he traveled further afield by hitchhiking and riding freight, before by 2009 busking in new york city. as he improved his performing, crockett organized a street band called the trainrobbers, which caught the attention of a manhattan-based representative for sony music. she signed the 26 years old crockett to a two-year management contract, although he rejected a publishing deal. eventually tired of life on the streets and the pending expiry of the contract, crockett relocated to northern california, where he combined working on farms and communes with performing for three more years. crockett then existed on the streets in paris, france, for a year, and briefly lived in spain and morocco.