Dr. Randy Hess

Dr. Randy Hess, 72, of Monkey Island, Oklahoma, passed away Wednesday, May 27, at his home, surrounded by family, after a three year battle with brain cancer.

Randy was born May 20, 1954, in Arizona to Louise and Bob Hess. He spent his early childhood in Illinois before proudly claiming Okmulgee, Oklahoma, as his hometown. The oldest of six children, he grew into a natural leader—responsible, steady, and admired. He had a gift for turning ordinary moments into memorable ones, and people were drawn to his easy charm and quiet influence.

A standout athlete at Okmulgee High School, Randy became a state champion in both basketball and football. His drive, discipline, and charisma carried him through life. He attended Wichita State University on a football scholarship before continuing his education at the University of Oklahoma, where he joined Sigma Alpha Epsilon. During his undergraduate years, he met and later married Debbie Dixon of Lawton. He began in pharmacy school but ultimately found his calling in dentistry, graduating from the OU College of Dentistry in 1981.

Randy returned to Okmulgee to open his dental practice, where he served patients for decades with skill, precision, humor, and compassion—though never the mushy kind. His early retirement left many patients disappointed, a small reflection of the much larger loss now felt by all who knew him.

At Grand Lake, Randy served several terms as president of the Cliff Homeowners Association and was one of “The 84” instrumental in Shangri La’s revitalization. In Okmulgee, he was a member of First United Methodist Church and served on the Citizens Bank Board, the Okmulgee Country Club Board, and the Okmulgee Memorial Hospital Board. He also traveled to Jamaica on medical mission trips with his daughters.

Randy and Debbie shared nearly fifty years of marriage filled with laughter, adventure, and devotion. As a father to Lauren and Joan, he modeled a strong work ethic and unwavering integrity. His strength shaped not only his daughters’ lives but also the lives of many who grew up around him. He was a proud “Grandy” to his grandsons, Hess and Henry, who brought him immeasurable joy - almost always accompanied by a real Randy smile or smirk.

An avid golfer, Randy recorded three hole in ones (two from the same sleeve of balls, within days of each other) and won a club championship at the Golf Club of Oklahoma. He played hundreds of courses around the world, commemorating each with a golf ball displayed in his home according to his personal ranking system. He loved boating, skiing, fishing, OU sports, reading, scuba diving, Harley Davidsons, traveling with friends, and the simple pleasure of finding the perfect place to sit—usually on his deck.

He was known for his unannounced visits - especially at dinnertime - his harmless gossip, his many catchphrases, and his practical jokes. He was happiest at the lake—Okmulgee, Eufaula, and Grand—where decades of unforgettable memories were made.

Randy was a best friend to many and maintained lifelong friendships with intention and loyalty. And, he did not like to hug.

He is already deeply missed and will forever be remembered and celebrated.

Randy was preceded in death by his daughter, Lauren, and his parents, Louise and Bob Hess.

He leaves behind his wife, Debbie; daughter, Joan and her husband, Cody Anderson; grandsons Hess and Henry; siblings Holly Martin and Don, Cindy Hess and Frank Duncan, Rob Hess and Margaret, Lou Anne Hess, and Rick Hess; 11 nieces and nephews and their spouses; 9 great nieces and nephews; and extended family, dear friends and classmates.

A tribute will be held Monday, June 29, from 2–4 p.m. at The Summit - Shangri La Golf Club, Monkey Island, Oklahoma. Though Randy rarely announced his presence, we kindly request RSVPs to Debbie Hess or Joan Anderson by June 25.

In lieu of flowers, donations may be made to Saint Francis Cancer Center, OU Health Stephenson Cancer Center, or the Oklahoma Golf Association Foundation.