Born on January 5, 1941, in Eddyville, Kentucky, he was the son of James Smith Holloway, Sr., and Eliza Belle Murphy Holloway.
Bobby enlisted in the United States Army in October 1963. On December 20 of the same year, he married Jo Ann Yates Holloway. After his military service, Bobby worked as a skilled electrician at Phelps Dodge Magnet Wire Co. and Reed Crushed Stone. However, it was his first love – farming – that truly defined him. He was the owner and operator of Holly Growers, Inc. and Chloe-Belle, Inc., where he successfully cultivated hydroponic tobacco plants, raising acres of Burley and dark-fired tobacco, and managed a thriving agricultural operation in Christian and Trigg Counties. Later in life, he found joy in landscaping, caring for homes and their surroundings with the same devotion he showed to his fields.
His work ethic was matched only by his character; Bobby was known for his honesty, kindness, and deep love for those around him. He was a devoted farmer who cared for his workers as if they were family.
An active member of his community, Bobby was a previously ordained Baptist deacon and was a member of Hopkinsville First United Methodist Church. He was a founding member of the Gracey Volunteer Fire Department and a 32nd Degree Mason at the Cerulean Masonic Lodge #875.
He was preceded in death by his parents and siblings: stepbrother James Smith Halloway, Jr.; William Donald Holloway; Lucy Mae Keller Goodwin; and Gary Allen Holloway, as well as his parents-in-law, Clyde Samuel Yates, Sr., and Thelma Marie McPherson Yates.
Bobby is survived by his loving wife of 62 years, Jo Ann Yates Holloway, of Gracey; his son, Anthony Yates Holloway, and wife Sherry, of Gracey; and his granddaughter, Chloe Lassiter Holloway, who was the light of his life.
Funeral services will be held at 2:00 PM, Sunday, February 1, 2026, at Goodwin Funeral Home, 138 Main Street in Cadiz, with Rev. Bradley Cornelius and Rev. Herb Case officiating.
Visitation will precede the service, from 10:00 AM until the service hour of 2:00 PM.
Burial with military honors will take place at 12:00 PM, Tuesday, February 3, 2026, at Kentucky Veterans Cemetery West, 5817 Fort Campbell Blvd, Hopkinsville, Kentucky.
The funeral service will be live-streamed beginning at 1:55 PM, Sunday, February 1, 2026, on our YouTube channel at the following link: https://www.youtube.com/watch?v=GZG1nN6MQZM
Memorial contributions can be made to the Trigg County Hospital Foundation, in memory of Bobby Gene Holloway, 254 Main St, Cadiz, Kentucky 42211.
