Holly James Gregory, 76
August 28, 1950 – November 4, 2026
Holly James Gregory, affectionately known by family and friends as “Hoochie,” was born on August 28, 1950, to the late Willie Bob Gregory and the late Ellen Ware Gregory of Pontotoc, Mississippi.
Holly was a beloved husband, father, grandfather, great-grandfather, brother, uncle, and friend. His life was filled with family, faith, love, and memories that will forever be treasured by those who knew him.
A proud graduate of Pontotoc Attendance Center, Class of 1970, Holly enjoyed playing basketball during his school years. He later shared his love of sports by coaching Little League baseball and softball. He was also a member of the Land of the Hanging Grapes. He had a love for music and dancing and enjoyed creating special memories with family and friends.
Throughout his working years, Holly was employed at Brookwood while also co-owning and operating his own upholstery shop with the late Ronnie Williams. He took pride in his work and in providing for his family. His journey eventually changed following a car accident, but his life continued to be a testament to strength and perseverance.
On July 24, 1971, Holly welcomed his beloved daughter, Melinda Janel Frison, into the world. On December 8, 1972, he united in holy matrimony with his beloved wife, Sylvia Ann Gregory. Together, they built a life and family filled with love, memories, and blessings, including their son, Montoya Undray Gregory.
Holly professed his faith and hope in Christ at an early age and became a member of Pontotoc Second Baptist Church. He later joined East Baptist Church, where he continued his spiritual journey. His faith was an important part of his life.
Holly was preceded in death by his parents, Willie Bob and Ellen Ware Gregory, and his siblings: Willie “Buddy” Gregory, Virginia Zinn, Elmo “Pete” Gregory, Velma Rose “Penny” Johnson, Mary Bell Gregory, Jerry Gregory, John “Tom” Gregory, Marie Paulette “Polly” Riddle, and Earnest Joe “E.J.” Gregory.
On November 4, 2026, Holly James Gregory answered the Master’s call and went home to be with our Lord and Savior, Jesus Christ. Though his earthly journey has ended, the love he shared, the lessons he taught, and the memories he created will remain forever.
To lovingly remember and cherish his life and legacy, Holly leaves his devoted wife, Sylvia Ann Gregory of Pontotoc, Mississippi; his daughter, Melinda Janel Frison of Pontotoc, Mississippi, and her husband, Michael Frison; and his son, Montoya Undray Gregory of New Jersey, and his spouse, Latisha Gregory. He also leaves three granddaughters: Tiarra Crawford, wife of Jack Crawford; Ranisha Cook, wife of Isaac Cook; and Sylicia Gregory. He leaves three grandsons: Randal Crayton Jr., husband of Keia Crayton; Andrew Phillips; and Chandler Love. His legacy continues through seven precious great-grandchildren: I’Rhianna Cook, Jack Mason Crawford, Isley Cook, EraBella Crawford, Marylinn Crayton, Harmony Rose Crayton, and Ivy Cook. He also leaves a special niece, Denita Pruitt, and her husband, Mirron Pruitt; Williene Foote Cooper and Diane Judon, who went above and beyond while taking special care of our loved one; along with a host of sisters-in-law, nieces, nephews, cousins, extended family members, and friends.
Though our hearts are saddened by his departure, we find comfort in knowing that his life was meaningful, his love was lasting, and his memories will never fade. Holly was more than a name. He was a husband, a father, a grandfather, a great-grandfather, a brother, and a friend. He was a man who lived, loved, laughed, and left behind a family who will forever carry his memory. His presence will be missed, his stories will be remembered, and his legacy will continue through the generations.
“I have fought a good fight, I have finished my course, I have kept the faith.” – 2 Timothy 4:7 (KJV)
Rest peacefully, Hoochie. Your work here is done. Your family will love you always.
Visitation will be Saturday, November 14, 2026, from 11:00 AM until 1:00 PM at East Baptist Church, 340 Clark Street, Pontotoc, MS. Funeral service will be Saturday, November 14, 2026, at 1:00 PM at East Baptist Church, 340 Clark Stark, Pontotoc, MS.
Please follow the funeral home link above for further information, or to send online condolences or memorial gifts.
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