Coming from modest beginnings, Hollingsworth had a humble upbringing, and throughout his early life until adulthood, he supported himself through manual labor.
He later commenced the study of law in the office of attorney William L. Brown, Esq and later admitted to the bar.
On April 29, 1837, in the District of Columbia, Hollingsworth married Eliza O’Brien, who died in May 1939 at the age of 21.
[1][4] On July 25, 1843, in Davidson County, Tennessee he remarried a widow, Mrs. Anna Bell Dozier Stump.
[1] They had four children during their marriage: Hollingsworth died on January 24, 1855, at his residence in Davidson County, Tennessee, after a lingering illness of several months.