Bobby Jack Dempsey, Sr., 80, of Benton, Kentucky, passed away at his home on Sunday, September 27, 2026.
Bobby was born on April 2, 1946, in Cleveland, Mississippi, to the late Jack Willard Dempsey and Doris Long Dempsey. He was a hardworking man whose life was centered around his deep love for his family, his faith, and his many friends.
After graduating from high school, Bobby proudly enlisted in the United States Army and served his country during the Vietnam War for more than two years. Following his military service, he spent many years working as a union insulator with Insulators Local #90 in Memphis, Tennessee, and later with Insulators Local #37 out of Evansville, Indiana, before retiring. Never one to sit still for long, Bobby’s carefree and spontaneous personality led him to own and operate Aurora Wine Beer and Spirits after retirement. He enjoyed staying busy at the store and meeting the many people who came through its doors until his health no longer allowed him to continue.
Outside of work, Bobby loved spending time outdoors. He enjoyed hunting, fishing, and riding motorcycles, as well as spending time at the lake. He especially appreciated the simple beauty of watching the sunrise and sunset over the water and taking a moment to sit back and enjoy life.
Bobby was a man who seemed to know almost everyone, and if you had ever met him, chances are he left an impression on you. He was a Mason and a longtime member of Alford-Hardin Masonic Lodge #925, and he proudly served as a Shriner for 20 years. A member of Hardin Baptist Church, Bobby cherished the fellowship he shared with his church family and enjoyed attending whenever he could.
Above all else, Bobby was a loving husband, father, grandfather, brother, and friend. His easygoing spirit, generous heart, and unforgettable personality will be deeply missed by all who were fortunate enough to know and love him.
He is survived by his two sons, Nicholas Dempsey (Katie) of Benton, Kentucky and Bobby Jack Dempsey. Jr. (Celestial) of Haiku, Hawaii; his two sisters, Betty Joyce Gillentine (Robert) of Sardis, Mississippi and Janett Morris (Woody) of Hilton Head, South Carolina; his brother, Glenn Dempsey (Joyce) of Michie, Tennessee; his four grandchildren, Griffin Dempsey, Elisa Dempsey, Addie Dempsey, and Olivia Dempsey; and several nieces and nephews.
He was preceded in death by his wife, Jeanine Quinn Dempsey; and his parents, Jack Willard Dempsey and Doris Long Dempsey.
Expressions of sympathy may take the form of donations to Main Street Youth Center, 513 S. 4th Street, Murray, Kentucky 42071.
Visitation will be held from 11:00 AM to 1:00 PM on Thursday, October 1, 2026, at the Life Celebration Center of Filbeck-Cann, 1003 Poplar Street, Benton, Kentucky 42025.
Funeral services will be held at 1:00 PM on Thursday, October 1, 2026, at the Life Celebration Center of Filbeck-Cann. Bro. Ricky Cunningham will officiate, and the burial will follow at Hardin Baptist Church Cemetery.
To share a memory or leave a message for the family, please visit Bobby’s Tribute Wall at www.filbeckandcann.com.
