Hillery Walter Sizemore was born 8 Jul. 1879 to Kern M. and Sarah Stapleton Sizemore in Pumpkin Valley, near Eidson, Hawkins County, TN. He was their second child with an older unnamed brother dying right after birth in Dec. 1876 and a younger brother Hugh being born in August 1881 and dying 10 Sept. 1887 aged 6 years and 1 month.

He married Ida Carter also of Pumpkin Valley on 30 Dec. 1899. They lived in a house that Hillery and his younger brother Tom built and it's where they raised their thirteen children. In January of 1937 Ida caught pneumonia and died. A couple of years later, his matchmaking son Charlie introduced him to a younger widow Tempie Hensley Moore and they married. They remained together until his death in 1973.

Hillery was a farmer and he and Ida were well known in the area for making fine wooden caskets. Hillery was an excellent carpenter and Ida hand-stitched the interiors. His carpentry skills are still evident in the large barn he and his sons built many years ago that is still in excellent condition although the homeplace was demolished about 2007. He and his sons operated a kerosene engine-powered grist mill on the creek bottom of the property and ground corn for neighbors for shares or for scarce money. Unfortunately, the mill was washed away in a flood in the 1930s. He farmed with horses and mules even as an old man and often grew tobacco higher than a man's head in the bottom ground. He was a hard worker and didn't tolerate anything less from his boys. A man firmly entrenched in 19th century upbringing, he never learned to drive although he owned an ancient coal truck and later an old International pickup truck up until his death. Whenever he and Tempie needed to go to Rogersville or Sneedville, their tenant Jason McMillan would be their driver.

He smoked a pipe of Prince Albert all of his adult life and occasionally liked a cigar. As a younger man he was known to like a bit of whiskey once in a great while (much to Ida's consternation) but otherwise wouldn't tolerate a drunk in his presence. He was a very stern character for the most part as most photos of him over the years depict but you could occasionally coax a smile out of him.

He was a lifelong Republican and was an election judge several times for the 3rd District of the Upper Clinch Precinct of Hawkins County, TN.

He lived almost his entire life in Pumpkin Valley except for a couple of years in the early 1920s when many of the family moved to Great Falls, SC to find work in the new cotton mills. He worked as a carpenter there building for the new industry and son Charlie assisted as a carpenter's helper although barely a teenager. After they returned from SC, he remained in Pumpkin Valley for the rest of his life until Alzheimer's disease required him going to a nursing home right before he died 2 Feb. 1973 at the age of 93. He's buried beside his first wife Ida in the Sizemore family cemetery on the homeplace.