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Ray was a man of faith, family, history, humor, and a genuine love for the community he called home.

Kenneth "Ray" Hollingshead entered his heavenly home on Friday, September 4, 2026, at the age of 88. A proud Sandite through and through, Ray was a man of faith, family, history, humor, and a genuine love for the community he called home. Arrangements are entrusted to the care of Mobley-Groesbeck Funeral Service of Sand Springs. 

Ray was born on August 11, 1938, in the family home in Sand Springs, Oklahoma, to Alva Clyde Hollingshead and Tula (Lay) Hollingshead. He grew up in Sand Springs and attended Sand Springs High School, graduating with the Class of 1956. During his high school years, Ray worked at the Cotton Mill to help support his family, demonstrating the strong work ethic and sense of responsibility that would remain a part of him throughout his life.

After high school, Ray proudly served in the United States Army. Following his active service, he continued serving his country through the Army Reserves and National Guard for an additional 23 years.

Ray’s love story with his beloved wife, Carol, began in a rather unique way. Ray’s sister, Bobby, was good friends with Carol June Puckett and asked if Carol would like to start “writing her brother.” The two began corresponding and “dated” for two years before they actually met. Their friendship blossomed into a lifelong love, and Ray and Carol were married on November 11, 1961.

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Ray found a way to turn his grief into a mission of helping others.

Ray and Carol lived in Shawnee while Ray attended Oklahoma Baptist University, where he earned his bachelor’s degree in education. They later lived in Mill Valley, California, where Ray continued his education and earned his master’s degree from Golden Gate Baptist Theological Seminary.

Together, Ray and Carol raised their family and eventually returned to Sand Springs, where Ray’s heart had always belonged. They also lived in Glenpool and Owasso over the years, but no matter where life took him, Ray remained a Sandite at heart.

Ray dedicated 25 years of his career to the Oklahoma Department of Corrections, working in probation and parole. While his children were growing up, he also worked for a short time distributing Lance crackers and other food products throughout the area. His children and the neighborhood kids especially remember the “expired” goodies that somehow found their way home from his job—much to the delight of the neighborhood children.

One of the most meaningful chapters of Ray’s life came through his involvement with Mothers Against Drunk Driving (MADD). After the devastating loss of his son, Charley, who was just 15 years old when he was struck and killed by a drunk driver while riding his bicycle, Ray found a way to turn his grief into a mission of helping others.

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His life was built around the people he loved, and his family will forever treasure the stories, laughter, lessons, and memories he left behind.

For many years, Ray devoted countless hours to volunteering with MADD and worked tirelessly to bring greater awareness to the dangers and devastating consequences of drunk driving. His involvement was deeply personal, but he used his experience and his voice to encourage others to make responsible choices and, hopefully, prevent another family from experiencing the kind of heartbreak his own family endured. Through his work with MADD, Ray honored Charley’s memory by helping to make his community safer for others.

Ray was a man of many interests. He loved watching television and could often be found with a good book in his hands. While he enjoyed reading about many subjects, his favorite was the Civil War. Ray was a true Civil War buff and history enthusiast. His children fondly remember him taking them to see military guns and helicopters when they were young, creating memories that they would carry with them throughout their lives.

His faith was an important part of who Ray was. He was a longtime member of Olivet Baptist Church, where he faithfully taught Sunday school for many years. He was also a member of the Disabled American Veterans (DAV) in Sand Springs.

Those who knew Ray will remember a man who was smart, funny, intelligent, goofy, and always ready with a joke. He was a master of the dad joke and had a way of bringing laughter to the people around him. He could be serious when he needed to be, but he also knew the value of having fun and making memories. His quick wit and unique personality made him unforgettable to those who knew and loved him.

More than anything, Ray was a devoted husband, father, grandfather, brother, and friend. His life was built around the people he loved, and his family will forever treasure the stories, laughter, lessons, and memories he left behind.

Ray is survived by his loving wife of nearly 65 years, Carol Hollingshead; his daughter, Andrea Lynn Bain, and her husband, Brannon; grandchildren, Liam Bain and Alyssa Bain; brothers, Jim Hollingshead and his wife, Mary Jo; along with numerous extended family members and friends who will miss him dearly.

He was preceded in death by his son, Charles Ray "Charley" Hollingshead; his parents, Alva Clyde and Tula (Lay) Hollingshead; and his siblings, Don Hollingshead, Tim Hollingshead, Alva Hollingshead, Wade Hollingshead, Barbara Burton, Melva Hoover, and Alan Hollingshead.

Ray’s life was one of service, faith, family, history, laughter, and love. He was a proud Sandite, a devoted husband and father, a grandfather who left lasting memories, and a man who never seemed to run out of a story—or a dad joke.

Though his chair may be empty and his voice may be quiet, the laughter he brought into the lives of others and the memories he created with his family will remain forever. And through the work he did with MADD, the memory of his beloved son Charley became part of a larger mission to protect others from the tragedy his family experienced.

Ray has gone home, but his stories, his laughter, his love, and the difference he made in the lives of others will live on in the hearts of all who knew him.