LaBeef stands 6' 7" tall and was given the nickname "Sleepy" from the appearance of his eyes. Born in Arkansas, he was raised on a melon farm and moved to Houston when he was 18. There, he sang gospel music on local radio and put together a bar band to play venues as well as radio programs such as the Houston Jamboree and Louisiana Hayride.
In the 1950s, as the rockabilly component of rock-n-roll became evident, LaBeef began recording singles in the genre; his first, "I'm Through", was issued on Starday Records in 1957. In 1964, he moved to Nashville and moved to a more solidly country style, recording singles for Columbia Records. His first genuine hit was 1968's "Every Day", which peaked at #73 on the U.S. Billboard Country charts. After moving to Plantation Records in 1969, he scored a second hit in 1971 with "Blackland Farmer", which charted at #67. Around this time LaBeef also starred in the horror movie The Exotic Ones. LaBeef transferred to Sun Records in the 1970s and continued releasing albums and touring widely; his popularity flagged in America but rose in Europe. The 1980s saw him sign to Rounder Records, where he released albums into the 1990s.