The area around what was formerly Spray, NC (now Eden), was fertile ground not only for tobacco plants, but for old-timey musicians as well. Many players, such as Norman Woodlief, Lonnie Austin, and, of course, Charlie Poole, came from this part of North Carolina. In the '20s and '30s, it would have been difficult for fans of the music to follow everything going on, with musicians playing in each other's bands, recording under aliases, and dreaming up new group names just to have something to call the band who was going to play or record that night. Woodlief moved to this area as a child in 1910, and was taught to play guitar by an older brother five years later. When the older brother got married and dropped out of several ad hoc bands he was in, Norman Woodlief stepped up to take over. One of these groups was led by Poole, soon to become a legend in old-timey music and the leader of one of the style's most enduring groups, Charlie Poole and the North Carolina Ramblers. Woodlief went on the road with this outfit, and in 1925 three of the musicians took jobs in Passaic, NJ, partly in an attempt to break in on the New York City recording scene. Poole made good on this, scoring a recording date with Columbia that produced the famous song "Don't Let Your Deal Go Down." But rambling with the Ramblers was too much for Woodlief, who wanted to stay at home and develop another one of his main interests, drawing. Shortly after these first Poole records were done, Woodlief went back to North Carolina, but would still work with the band in local engagements.
He continued recording, including a series of sides for Gennett in 1929 with Posey Rorer and Walter Smith, tracks with the Virginia Dandies for Crown, and a new session for Columbia as the Carolina Buddies. In 1938, Woodlief was working as a sign painter, a career he shares in common with fellow guitarist Tal Farlow. Woodlief's new musical group was called the Four Pickled Peppers, and they recorded two sessions for Bluebird with fellow Spray-er Lonnie Austin on fiddle for the second of these. World War II disrupted much professional musical activity, and many players such as Woodlief wound up retiring from professional music when it was over. Eventually, he was sought out by old-timey music enthusiasts in the '70s and did some new recordings during his senior years.