Bailey said he began racing at Playland Park near Houston in 1954. He won the track championship there in 1959, establishing himself as a competitive local talent before stepping up to the national scene. His progression through the ranks reflected the independent, self-funded character that defined his entire career.
Bailey entered NASCAR's Grand National series in 1962 and continued competing at the top level through 1993, though always as a part-time independent rather than a full-season team driver. Over those three decades he made 85 starts, an achievement that reflects extraordinary perseverance given the financial demands of the sport on drivers without factory or major sponsor backing.
Darlington Raceway was one of Bailey's favourite venues, and he became a three-time member of the UNOCAL/Darlington Record Club at the famed South Carolina oval. He made his final career start in the 1993 Southern 500 at Darlington, a fitting farewell to the track most associated with his career.
One of Bailey's most notable competitive campaigns came in the 1972 NASCAR Grand American division. He won the pole for the season opener at Daytona International Speedway and took a victory at Nashville. He went on to finish second in the national championship standings for that season, behind champion Wayne Andrews — the strongest title result of his career.
Bailey holds a singular historical footnote in American motorsport: he was the first driver to take a qualifying lap for the inaugural Brickyard 400 in 1994 at Indianapolis Motor Speedway. Though the race itself marked a new chapter for NASCAR, it was Bailey — the consummate independent racer — who led off qualifying, connecting the sport's grassroots past to its expanding future.
Bailey died of heart failure on April 17, 2003. Richard Petty, who raced alongside Bailey for virtually his entire career, offered a tribute that captured Bailey's standing within the NASCAR community: "Our sport was built by people like H.B. Bailey. H.B. was a racer through and through, and the sport is better off because he was a part of it. We will miss him."
Bailey's son Joe Dan served as his father's mechanic throughout his racing years and later built a career as an engineer for major NASCAR operations. Joe Dan worked on Bob Whitcomb's 1990 Daytona 500-winning team and was part of the Richard Childress Racing squads that claimed the NASCAR Cup Series championships in both 1993 and 1994, extending the Bailey family's contribution to the sport well beyond H. B.'s own driving career.