Henry Grady Woodruff, lawyer and member of the Texas legislature, son of John Warren and Fannie Lee (Lewis) Woodruff, was born in Wise County, Texas, on August 9, 1893. He was the oldest of nine children.
At some point Woodruff attended Decatur Baptist College and Baylor University. Apparently he had an early career in teaching. He was listed as superintendent of schools at Jermyn, Texas, on his draft registration card in May 1917. He served as a private in the United States Army during World War I. By the time of the 1920 census, he worked as a teacher in Wise County. Woodruff graduated with a law degree from the University of Texas Law School in 1927 and practiced law in Decatur.
He was elected to the Texas House of Representatives from Wise County (District 48) and served three terms in the House from 1925 to 1931. He then served in the Texas Senate from 1931 to 1939. During his first term in the Senate, he served as president pro tempore of that body. Woodruff was a member of many committees during his service in the legislature, and at various times as a state senator, he chaired the Contingent Expenses, Military Affairs, and Public Land and Land Office committees. Upon leaving office in 1939, he resumed practicing law in Decatur.
Henry Grady Woodruff married Ethelyne Morgan on December 25, 1934, and they had one son, Morgan. Woodruff died in Decatur, Texas, on December 23, 1962. He was buried at Oak Lawn Cemetery on December 26, 1962.