Henry Joseph Holloway was the fifth child of ten born to George Washington Holloway and Elvira Henton Holloway. In his youth, he attended local country schools first in Monroe County and then Butler Township of Harrison County, Missouri. Henry and his brothers helped their father on the farm, dividing the work. His brother "Pryor" had the responsibility of "chore boy" for cattle, sheep, hogs, and chickens, while the older boys, including Henry did the field work. His twin sisters Jearldine Rebecca and Hannah Elizabeth, and youngest brother Jasper worked about the house and garden.

At age 18, with his brother James, Henry enrolled and joined at Private, Co., D. 23 Reg't Missouri Infantry, the Union Army for duty on August 24,1861 at Eagleville, Missouri, for a period of 3 years. His father died one week later on 1 September 1861. Henry's brothers John Casper Holloway and Thomas Guy Holloway were in the Civil War, details unknown.

Henry was described as five feet ten inches tall, fair complexion, blue eyes, red hair, and by occupation when enlisted a farmer. "Jim" and Henry were sent to Tennessee, while his brother Richard "Pryor" served in Missouri. Henry and Jim were with General Prentiss at the Battle of Shiloh in west Tennessee. Jim was captured there and sent to the dreaded Confederate prison at Andersonville. Henry was killed on the first day of this battle, cause of death was "musket ball through the body."

Henry was single and preceded in death by his father and younger sister Mary Kay Holloway.

The Battle of Shiloh in west Tennessee, the bloodiest of the Civil War, was named after a church on the battlefield and is also called the Battle of Pittsburgh Landing. In the two days of battle, Union forces suffered about 13,000 casualties, and the Confederacy lost about 10,700 men.