Early was born in Watts Creek, Whitley County, Kentucky, USA, on 8 October 1849. He was the first child born to parents David Dryden Early (1818–1892) and Mary Ann Sears (1828–1878). He had seven siblings: Thomas Jesse (1852–1888), Margaret Rose (1855–1940), Sophronia Elizabeth Cloyd (1858–1933), James Madison (1862–1929), Grant (1864–1898) and Sidney Ann Barton (1868–1929). In his late life, he still remembered distinctly seeing both Confederate and Union troops tramp past his father’s farm in late 1861. After attending school in Williamsburg, he started his teaching career and taught for the next 10 years.
On 4 September 1875, Early married Eliza Ann Berry, with whom he had three children: Lura Bertha Macky (1874– 1937), Edna Allen (1879–1977) and Robert Brown (1882–1934). In 1879, the family moved to Texas, where he took a government contract to haul the mail between Sulphur Springs and Mineola. He gave up the mail contract after four years and moved to the Indian Territory (present-day Oklahoma), where he worked as a carpenter. In 1884, his wife passed away at the age of 28, and he moved back to Kentucky the same year. In 1886, he remarried to Sidney Ann King (1863–1948). The couple had six children: Lena Agnes Copes (1887–1984), Magnolia Pierce (1889–1981), Elden Ernest (1890–1966), Virginia Peace (1895–1994), William David (1899–1977) and Mary Etta Phillips (1904–1995). Shortly after moving to Kentucky, he and a cousin bought a store in Mahan Station, where he worked as a merchant until the store burned down five years later. He started working as a carpenter again, as well as a contractor for keeps.
In 1897, the family moved to Corbin. Early was the first Sunday school superintendent at the First Methodist Church. For 12 years, from 1917 to 1929, he was the city’s police judge.
At the age of 70, Early took up woodcarving, but had to quit at 108 when his hands became too shaky.
As of his 100th birthday, Early was keeping a diary about his daily life, which he started 20 years prior. At the time, his hearing was not perfect, but he was still able to read without wearing glasses. At the time, he had seven living children, in addition to 27 grandchildren, 40 great-grandchildren and five great-great-grandchildren. He claimed to have no ‘’formula’’ for his longevity but assumed it could be linked with his “early-to-bed, early-to-rise” daily routine. At the time, he was still smoking his pipe once a day.
Early died in Corbin, Kentucky, on 9 October 1960, one day after celebrating his 111th birthday. He had been in good health and spirits on the date of his final birthday and celebrated the event with a party attended by 20 friends and family members. The following day, he fell ill after dinner, and died soon after of undisclosed causes.