Born Richard Henry, this North Carolina country blues artist enjoyed a unique niche in his later life as a folk festival and club performer, bringing great pleasure to blues fans in a period when many older artists in this genre were passing away. He grew up on the North Carolina coast in the '20s and '30s, an era when bluesmen still played on street corners and juke joints were hopping at night with live music. The South Carolinian bluesman Fred Miller was one of his first big musical influences, and Henry assumed the traditional apprentice role in the country blues relationship, meaning he would "go around" with Miller to various functions where a few coins would be made and some blues would be sung. Henry quickly took over the vocal duties since his partner's singing abilities was in direct contrast to his excellent guitar technique. Miller moved to New York and Big Boy Henry began a series of journeys to the city in order to continue their relationship. This led to meetings with other Piedmont bluesmen such as the whooping harmonica player Sonny Terry and his sidekick Brownie McGhee. In 1951, Henry got the opportunity to record with backup from this famous duo, the blues equivalent of getting Rembrandt and Cezanne to help decorate. In a typical development in American blues recording history, these tracks were canned rather than released, although a release was finally arranged decades later. A defeated Henry limped back to his coastal digs in New Bern and decided to give up playing blues.
In the '50s and '60s, he worked on fishing and oystering crews and also ran a grocery store. He also did a touch of preaching in local churches, perhaps following the advice of fellow bluesman Son House as expressed in the song "Preachin' Blues": "I'm gonna become a Baptist preacher/And then I won't have to work." In 1971, he moved back to his first family home in Beaufort, not realizing that this would lead to a group of younger local musicians recognizing him. All it took was a little bit of their subsequent encouragement and he was ready to return to playing. As he got older, the guitarist's abilities were naturally hampered because of arthritis, but he still picked inventive single-string blues lines, tinkering with rhythms and bar-line blues structures with as much freedom as Lightnin' Hopkins. Younger North Carolina blues players such as the harmonica virtuoso Chris Turner and guitarist Billy Hobbs enjoyed the challenge of following the older man, who never failed to set the powerful musical mood known as "deep blues feeling." His vocal style was considered as powerful as ever in his senior years as he created his own inventive versions of blues standards and wrote his own songs as well, often touching on current events. The powerful song "Mr. President," written as an angry response to social welfare cuts undertaken by Ronald Reagan in the '80s, won him a W.C. Handy Award from the Blues Foundation. In 1995, he received the North Carolina Arts Council Folk Heritage award.
Henry's involvement with music goes well beyond performing. He has been actively involved with older members of his community in attempts to maintain and record one of the important coastal traditions, the work songs sung by himself and other African-Americans who fished on menhaden boats. His activities included organizing a group of retired fisherman into a singing group, the Menhaden Chantey Men.