Shortly after the start of World War II, the family moved to Connecticut.
He then moved to bluegrass before he and his friend, John Sligar, changed to rockabilly in 1954.
[1] The musical style as such had already existed and had been played by musicians such as Hardrock Gunter and Roy Hall.
After that, he worked in his family's business and helped his father, who had previously suffered a heart attack.
After that, Flagg started a bluegrass band called Hobo Bill and the Last Ride.