Sheryl Lee Letterman

Sheryl Lee (Hess) Letterman, 74, of Springfield, Missouri, passed away Sept. 29, 2025, in Evansville, Indiana. She was surrounded by her family.
She was born Aug. 8, 1951, in Cameron, Missouri, to Bill and Evelyn Hess. Sheryl was the oldest of six siblings and loved being part of a big family. She graduated from Lee's Summit High School in 1969 and attended Drury University in Springfield where she graduated in 1973 with a bachelor's degree in history.
Shortly after college, she met the love of her life, Danny Letterman. They pair were married on Nov. 19, 1976. They loved to travel together and took many road trips across North America over the years, from the crystal blue lakes of Banff National Park in Canada to the wonder of the Grand Canyon in Arizona and the bayous of Louisiana.
On Dec, 4, 1978, they welcomed their first child, a son, Adam Allen; and two years later, their daughter, Robin Lee, was born. The family resided in Midtown Springfield where Sheryl took a job as the first permanent employee of the Springfield Contractors Association. In those early days, the organization consisted of a file cabinet in her house, but grew to be more than 300 members strong. Much of the family's life included SCA events, like the annual pig roast. She retired as executive director in 2015.
Sheryl was active in the community, dedicating much of her time to the Women in Need of the Ozarks. She helped launch the organization and served on its first board of directors. For decades, she served on the WIN scholarship committee, helping women who needed a hand up, not a hand out. She continued her service until March of this year.
Sheryl was a collector of people and a friend to all. Once she collected you, you were her friend for life. She regularly kept in touch with her college roommates, her monthly lunch club known as LEAP, her "old lady fitness class" friends, the four book clubs she attended and so many more. She made a point to learn her waiter's name and never met a person she couldn't have a 10-minute conversation with. She'd talk to every person in a room at a party – and not just about the weather, she wanted your life story. Sheryl loved a good bit of trivia and hated a busy street, especially if it meant driving to the south side of Springfield. She collected stars and had a connection to the celestial spirit.
Later in life, she spent much of her time with her grandchildren: Ryan (17) and Maycie (5). She and Ryan had a special relationship and enjoyed the everyday together, such as visiting the Springfield Art Museum and simply enjoying a bucket of KFC in the park. Sheryl spent every Sunday morning with Maycie, reading library books, playing dress up and watching Maycie perform her favorite Disney songs with glee.
Sheryl was preceded in death by her parents, her husband, her daughter and her sister Connie. She is survived by her son, Adam, his wife Emily, and their daughter Maycie; grandson Ryan Brandenburg, and his father, John; and siblings Kathy, Billie, Russ and Laura.
A celebration of life will be held at 10 a.m. on Oct. 11 at Greenlawn East Funeral Home, 3540 E. Seminole, Springfield. Interment at Eastlawn Cemetery will take place at a later date. In lieu of flowers, the family requests donations to the WIN organization in Sheryl's memory. Donations can be made at givebetter.com/SLetterman