Like his brothers Bobby (1944–2014) and Cecil (1947–2013), Harry took up instruments, playing bass guitar before reaching his teenage years.
In 1960, when he was fifteen, Sam Cooke signed the act to his SAR Records label, having told the brothers – and their father – that he was willing to work with them.
Friendly Womack made Sam Cooke promise him that the brothers would continue to sing gospel and not what he referred to as "the devil's music".
He and the other Valentinos and Cecil Womack contributed background vocals to Bobby's solo records starting with the 1970 release, My Prescription.
Harry and the brothers were promptly featured in the background of Bobby's breakthrough hit, "That's the Way I Feel About Cha" as well as "Woman's Gotta Have It" from 1972.
Harry possessed an alluring, confident stage presence with the surprising ability to 'spark' a gig through "seamless" and flawless improvisation.
He was very soft-spoken, warm "natured", laid back and reflective, many times those qualities were mistaken for weakness, aloofness or lack of care and concern.
Harry seldom drove, preferring instead the accompaniment of the groups roadie/confidant "Bill Crite", who always made himself available to the band members, on and off the road, their friendship was admirable.
Bobby held church that night and for all of those present, before they left, I know they felt the spirit moving into their bodies and rocking them with a whole lotta' soul.
Harry's last professional recording was singing background (tenor) on Bobby's album, Lookin' for a Love Again, released in January 1974.
Bobby further expounded on his brother's death in an interview quote about the song and in Understanding wiki article under the Harry Hippie section.