A distant relative of Davy Crockett,[4] Charley was born in San Benito, Texas, United States.[5] The son of a single mother[1] with an older brother and sister, Crockett was raised in a trailer park in Los Fresnos, Texas.[4][6] His mother relocated the family to Dallas,[6] and Crockett spent the summer months with his uncle, who lived in the French Quarter of New Orleans.[7] Upon leaving high school, at the age of 17 Crockett decided to travel with his guitar, acquired by his mother from a pawn shop. Crockett noted "I taught myself how to play and started to write songs immediately, without any chord knowledge or anything. I didn't know what key I was in for 12 years, but my ear was really good, and I could play in any key and any chord. I just didn't know what it was."[1] His early musical influences came from hearing hip hop, and became fascinated with the samples used. Crockett said "I got into Curtis Mayfield through samples of his songs by other artists, and Nina Simone was through a sample. Even J. Cole, I was listening to a song of his ("Kenny Lofton"), and it was based on the sample from the Manhattans version of "Hurt".[5]

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.[7][4] 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.[1][7] 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.[1][4][5] Crockett then existed on the streets in Paris, France, for a year, and briefly lived in Spain and Morocco.[3]

During these years, Crockett struggled to stay the right side of the law. In the US, he was arrested for the possession of cannabis in 2014, for which he remains under probation. Worse followed, courtesy of his brother, who coerced Crockett into a criminal operation. Crockett's name was forged onto documents, and so he evaded the eventual potential prosecution, however his brother was sentenced to seven years in prison for dealing in around $40 million worth of securities fraud. Crockett noted later, "People think my story is far-fetched, but the thing is, I’ve toned it down."[6]