Holmes' parents were sharecroppers,[6] who opened the Blue Front Cafe in 1948, the year after he was born.

At the same time, Tommy West, a Hill country blues musician was also teaching Holmes how to play in that idiom.

Holmes eventually incorporated some of the techniques he learned from West into his own playing, including using the low E string for a droning bass line.

"[12] Holmes was initially recorded by several people in the late 1970s and early 1980s, including Alan Lomax and David Evans.

It appeared in 1991 on a Wolf Records compilation album, Giants of the Country Blues Guitar - Vol.

Then in October 2005, Jeff Konkel visited the Blue Front Cafe and returned on November 17, 2005, to record Holmes.

[18] In 2010, Broke and Hungry Records released Holmes' fourth album, Ain't It Lonesome.

In 2008, Holmes and the Blue Front Cafe were featured in the documentary M for Mississippi produced by Konkel and Roger Stolle.

[17] On October 22, 2012, Holmes appeared with Terry "Harmonica" Bean at World Cafe Live on WXPN as part of the Mississippi Blues Project.