"Oh, Leadbelly" is a tribute to the American blues musician, Lead Belly, also known as Huddie William Ledbetter. Lead Belly was a prolific singer and songwriter with a powerful voice and a unique guitar style, and his influence on blues and folk music is immeasurable. The song reflects on Lead Belly's impact on the music world, particularly on the songwriter who heard his music as a teenager. The lyrics describe how Lead Belly's music stirred the soul and made people weep and moan with its emotional power. The song also references Lead Belly's time in prison, where he served multiple sentences for various crimes. Lead Belly was famously pardoned by the governor of Louisiana after he sang a plea for clemency, which was recorded and sent to the governor. The song reflects on the moment when Lead Belly was told he had been pardoned and was free to leave prison, and how his music continued to inspire even after he left prison behind. The song ends with a reference to Lead Belly's most famous song, "Goodnight Irene," which became a hit and helped to expose Lead Belly's music to a wider audience. The song suggests that Lead Belly's legacy as a musician will continue for generations to come.