Lead Belly's volatile nature sometimes led him into trouble with the law. In 1915 he was convicted "of carrying a pistol" and sentenced to do time on the Harrison County chain gang, from which he miraculously escaped, finding work in nearby Bowie county under the assumed name of Walter Boyd. In January 1918 he was imprisoned a second time, this time after killing one of his relatives, Will Stafford, in a fight over a woman. In 1918 he was incarcerated in Sugar Land, Texas, where he probably learned the song "Midnight Special".[4] In 1925 he was pardoned and released, having served seven years, or virtually all of the minimum of his seven-to-35-year sentence, after writing a song appealing to Governor Pat Morris Neff for his freedom. Lead Belly had swayed Governor Neff by appealing to his strong religious values. That, in combination with good behavior (including entertaining by playing for the guards and fellow prisoners), was Lead Belly's ticket out of jail. It was quite a testament to his persuasive powers, as Neff had run for governor on a pledge not to issue pardons (pardon by the governor was at that time the only recourse for prisoners, since in most Southern prisons there was no provision for parole). According to Charles K. Wolf and Kip Lornell's book, The Life and Legend of Leadbelly (1999), Neff had regularly brought guests to the prison on Sunday picnics to hear Lead Belly perform.
In 1930, Lead Belly was back in prison, after a summary trial, this time in Louisiana, for attempted homicide — he had knifed a white man in a fight. It was there, three years later, that he was "discovered" by musicologists John Lomax and his eighteen-year-old son Alan Lomax during a visit to the Angola Prison Farm. They were enchanted by Lead Belly's talent, passion, and singularity as a performer and recorded hundreds of his songs on portable aluminum disc recording equipment for the Library of Congress. They returned to record in July of the following year (1934). On August 1, Lead Belly was released (again having served almost all of his minimum sentence), this time after the Lomaxes had taken a petition to Louisiana Governor O.K. Allen at Lead Belly's urgent request. The petition was on the other side of a recording of his signature song, "Goodnight Irene." A prison official later wrote to John Lomax denying that Lead Belly's singing had anything to do his release from Angola, and state prison records confirm that he was eligible for early release due to good behavior. A descendant of his has also confirmed this. For a time, however, both Lead Belly and the Lomaxes believed that the record they had taken to the governor had hastened his release from Angola.