Benny Ray Cress

Benny Ray Cress, age 60, of Cumberland, Kentucky, left this world unexpectedly on Friday, December 5, 2025, at Harlan Appalachian Regional Hospital, leaving behind a trail of laughter, love, and cherished memories that will echo through the hills he called home.

Born on December 20, 1964, to the late Denver and Irene Halcomb Cress, Benny lived life with a contagious joy that drew people to him like moths to a flame. He was a simple man in the best sense of the word, genuine, down-to-earth, and real. His belief in God guided him quietly through life, and his love for the outdoors was where his spirit truly soared. Whether he was hunting in the mountains, casting a line in the creek, or camping under the stars, Benny found peace in nature's embrace.

Before returning home to his beloved Kentucky hills, Benny worked for Asplundh Tree Experts in Stanford, Kentucky, where his strong work ethic and friendly nature made him a valued member of the team. But it was in the company of family and friends where Benny truly shined. He was the heartbeat of every family gathering, the one who could turn an ordinary moment into something special with his quick wit and mischievous grin. His pranks and jokes were legendary, delivered with perfect timing and a twinkle in his eye that let you know you'd been had by the master.

Benny's love for adventure extended beyond the wilderness. He traveled often with his niece to concerts and trips out of town, always ready for the next experience. At home, you'd likely find him glued to the television watching "Cops" and other law enforcement shows, his favorite way to unwind after a day well spent.

But above all else, Benny loved his family with his whole heart. When Benny loved you, you knew it, because he held nothing back. He was caring, compassionate, and fiercely loyal. His family, each one, knew they held a special place in his heart. He had a way of making everyone feel important, heard, and loved.

Benny was preceded in death by his parents, Denver and Irene Halcomb Cress; his brother, Marion Wayne Cress; his sister, Vernia Day; nephews, Billy Cress, Brandon Cress, Christopher Cress, Patrick Cress, Ray Maggard, niece, Tasha Adams and a great-niece, Kerra Kay Cress.

He leaves behind to mourn his passing but cherish his memory: his son, Todd Cress; his daughter, Cayla Wilson; his brothers, James (Doris) Cress, Verlin (Connie) Cress, Bill (Libby) Cress, and Eddie (Linda) Cress; his sisters, Belvia Short and Eva Sue Cress (Steve); six grandchildren; and a host of nieces, nephews, other relatives, and friends whose lives were made richer by knowing him.

Though Benny's time with us was cut short, the memories he created will live on forever. His laughter will echo in our hearts, his pranks will bring smiles through our tears, and his love will continue to wrap around us like the Kentucky mountains he treasured.

Visitation will be held Tuesday, December 9, 2025, from 11:00 a.m. to 12:00 noon at Cumberland Valley Funeral Home.
Burial will follow at Stoney Fork Cemetery in Leatherwood, Kentucky.

Cumberland Valley Funeral Home is honored to serve the Cress Family.

Rest easy among the hills you loved Benny. Your work here is done, but your love remains forever.

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