Harold Dennis Jackson, age 66, departed this life on Sunday, April 25, 2021, at his home surrounded by his loving family. Born November 1, 1954, in Corbin, Kentucky to the late Harold Thomas Jackson and Jewell Ellison Jackson. He was a member of the New River Baptist Church. He is survived by his loving wife Judy “Castle” Jackson; children, Paige Jackson Moore of Union, Kentucky, Brandon Jackson of Lexington, Kentucky, Tyler Jackson and wife, Trudy of Corbin, Kentucky; nine grandchildren, Sydney, Taylor, Reese, Chris, Ian, Nathanael, Mathias, Jeremiah, and Zack; brother, Jim Jackson and wife, Debbie of Corbin, Kentucky; two special friends, Will Burke and Keith Newport, several nieces and nephews, family and friends. Dennis and his wife, Judy have been longtime business owners of Tennessee Outdoors and Value Mart Furniture in Scott County, Tennessee before retirement. Dennis and Judy have been very active community leaders in their community. Friends may visit with the Jackson family on Wednesday, April 28, 2021, from 10:00am until time for the funeral services at 12 noon at the Chapel of Four Oaks Funeral Home in Huntsville with Bro. Kermit Phillips officiating. Music will be provided by Bro. Kermit Phillips. Burial to follow at 2:30pm eastern standard time at Pine Hill Cemetery, Master Street, Knox County, Kentucky 40701. Pallbearers will be Tyler Jackson, Brandon Jackson, Taylor Moore, Chris Jackson, Will Burke and Keith Newport. In Lieu of Flowers, family is requesting donations be made to the National Diabetes Foundation, American Heart Association, or National Kidney Foundation. You may light a candle tribute in his honor by visiting www.fouroaksfuneralhomes.com. Due to COVID-19, and in consideration of the executive order of Governor Bill Lee, we ask that attendees maintain appropriate social distancing, observe current health guidelines, and be considerate of all others in attendance. Masks are required. Four Oaks Funeral Home in Huntsville has been entrusted with final arrangements for the family of Harold Dennis Jackson. This obituary is courtesy of the Vankirk-Grisell Funeral Home.