Flippen was a recipient of the North Carolina Folk Heritage Award in 1990.
Flippen was raised on a farm in Surry County, North Carolina, where he first played the banjo during his childhood. His father was an accomplished old time banjo picker, as were his uncles and brothers. During his youth he visited his fiddling uncle John Flippen, quickly turned to playing the fiddle and started playing with the area's noted bands and musicians, among them the Green Valley Boys led by Glenn McPeak, with Esker Hutchins and Leak Caudill. Esker became an important influence on Flippen's fiddling style, which included a heavy bow shuffle and bluesy notation.
In the late 1960s he was asked to fiddle with the Camp Creek Boys, after Fred Cockerham's departure. From the 1970s on, Flippen belonged to the Smokey Valley Boys, an outfit that preserved Flippen's unique musical abilities on recordings. The band also earned awards at numerous fiddling competitions, before disbanding in 1985. In 1990, the North Carolina Folk Heritage Awards honored Flippen, who was recognized for a unique style of string fingering. Flippen was also renowned for his original compositions, which include "Benton's Dream," "Fiddler's Reel," "Sally in the Turnip Patch," and "Smokey Valley Breakdown."
During his career, Flippen took first place numerous times in fiddle and band contests. He won seven times at the Old Fiddler's Convention in Galax, Virginia; three times at the Union Grove Old Time Fiddlers' Convention; and at the Mount Airy Fiddlers Convention, among many others. He also played at the Newport Folk Festival, the 1982 World's Fair in Knoxville, Tennessee, the Festival of American Fiddle Tunes, the Smithsonian Institution, the Library of Congress, the Appalachian String Band Music Festival in Clifftop, Fayette County, West Virginia, and many more highly esteemed venues. In 2008, at the age of 88, he headlined the Berkeley Old Time Music Convention in California.