Huddie Ledbetter, better known as Leadbelly (1888-1949), was one of the most unique, fascinating and influential singer-songwriters of the foundational American blues and folk traditions - a starting point of the contemporary singer-songwriter development. Born in 1888 on Jeter Plantation, near Mooringsport, Louisiana, he belonged to the first generation of blues artists - formed by itinerant African American musicians with outsider lifestyles, seeking social advancement in spite of the Jim Crow south. Stylistically, however, his extensive and varied repertoire has earned him a differentiated and sometimes peculiar status in blues studies and popular music history, as he is often considered a songster rather than a bluesman. A multi-instrumentalist who could play guitar, piano, mandolin, harmonica, violin and accordion, Leadbelly gained notoriety as the ‘the King of Twelve-String Guitar’, developing a distinctive, powerful drive that has had a profound impact on the evolution of popular music. Throughout the decades, his obscure and appealing persona has constantly inspired further reinterpretations of material he composed or first popularised by musicians from different scenes and styles, ranging from the mid-twentieth century folk revival, roots and surf rock of Pete Seeger, Creedence Clearwater Revival, and The Beach Boys respectively, to the more recent grunge and garage rock sounds of Nirvana and the White Stripes. Leadbelly’s case poses significant challenges for any researcher, writer or reader discussing his music, life, and legend. Many episodes of his life remain unclear, others have been interpreted in contradictory ways, and the artist himself continuously reconstructed his persona through malleable stories. The aim of this chapter is to offer a reliable and nuanced framework for approaching such a complex character, based on the most relevant stages of Leadbelly’s artistic and life trajectory. In this process, I will refer to significant events and circumstances, relating them to particular songs and styles, and incorporating previous discussions about the musical, socio-political, and racial meanings and implications of his remarkable journey. Rambling singer-songwriters in the deep south Leadbelly grew up around Caddo Parish, Louisiana, a frontier, rural area that hosted one of the highest concentrations of African Americans west of the Mississippi River. As a strong, rambunctious young man, he proved to be an effective agricultural worker, picking cotton and learning about farming and cowboy culture, and, by the time he was fourteen, he had won a local reputation for his guitar playing and singing.