Robert Ray “Bob” Simmons, 68, passed away at 3:41PM on Friday March 13, 2026, at Select Specialty Hospital in Evansville IN. He was born in Fairfield on December 21, 1957, to Jack and Frances (Smith) Simmons.
Bob grew up in Fairfield, IL, with his two brothers, Jackie and Troy Simmons. After high school, he joined the U.S. Army and was stationed at Fort Riley, KS, where he excelled as a Big Red One Combat Engineer. Upon returning to his hometown, he worked alongside his father on an oil rig. In 1986, Bob and his family moved to Orlando, FL, where he became a professional painter, working on skyscrapers and high-end celebrity homes. Bob returned to Fairfield in 2012, where he lived out his years in his childhood home. He was well liked by everyone who knew him and deeply loved by his family. Known for his big heart and intriguing stories, his smile could light up a room, earning him the nickname “Smiley Bob.” He will always radiate in our hearts and live forever in our memories.
He is survived by his children- Richard “Rick” Simmons of Fairfield and Teresa Simmons of Cisne; brothers- Troy Simmons of Chicago and Jackie Simmons of Carmi; his best friend Christine Simmons also survives. He was preceded in death by his parents, and stepfather- Ivan Bell.
A memorial service in Bob’s honor will be held on Friday April 3, 2026, at 12PM at the Johnson and Vaughn Funeral Home with burial of ashes at Maple Hill Cemetery. Military rites will be provided by Anthony Wayne Post #176 American Legion and the Wayne County Post #4535 VFW. Visitation will be held from 11AM until the time of service at the funeral home.
Johnson and Vaughn Funeral Home is in charge of all the arrangements.
