Robert "Bob" Stephenson

Robert (Bob) Thomas Stephenson, 70, passed away suddenly on June 1, 2026, at Lakeland Regional Health Medical Center after suffering a severe stroke. Bob was born in Madison, Indiana to Robert L. Stephenson and Julia Costin Stephenson. The family relocated to central Florida in 1958.

Known for his levity and sense of humor, as evidenced by being named the “Wittiest” Notable his senior year of high school, Bob was always ready with a story or an impersonation to regale his friends and family. He attended Polk Community College earning a tennis scholarship his freshman year and a drama scholarship the following, where he discovered his love of the stage. His role as Snoopy in the production of “You’re a Good Man, Charlie Brown” was his favorite which further ignited this passion.

Bob’s talents and interests primarily focused on creativity and entertainment. Even before graduating from Winter Haven High School Bob began his career in broadcasting at WINT-FM located in the historic Orange Dome playing “beautiful music” on very large reel to reel tapes, three hours at a time. His voice was first heard on WSIR (“1490 on your radio dial”) where he learned every aspect of how the radio industry worked and truly set the course for his life.

His career as an on-air personality, programmer, producer, director, and manager took him to multiple stations in Florida, North Carolina, Texas, Illinois, Wyoming, California, and most recently streaming stations like “That 70s Channel”. He often served as the morning host playing music, reading news, traffic, and weather, as well several stints as a talk show host on nationally syndicated stations. His radio career covered many genres including classic rock, Christian, Top 40, 70’s, and his favorite smooth jazz. Bob also had a substantial career in voice over work including commercials, video games, and documentaries.

Bob also enjoyed acting appearing in numerous plays across the country, television shows, and short duration films. He also directed local theater productions and consistently supported these organizations. Bob announced ski shows at Cypress Gardens and did play-by-play for the Boston Red Sox spring training games, Wake Forest University football, and Polk State basketball.

Bob’s many passions extended beyond the entertainment industry to include baseball, golf, and fishing. Although an avid Tampa Bay Rays fan in his later years, his favorite player was Mickey Mantle of the New York Yankees and even has a glove with “The Mick’s” autograph. Another highlight he often spoke of was being bat boy for a Washington Senators spring training game in the early 1960’s, being close to the action and getting to meet well known ballplayers in a more relaxed setting.

Bob was preceded in death by his parents as well as his brother Danny Stephenson of Winter Haven.

Bob is survived by his beloved children daughters Julia Siebert and Jenni Stephenson of Sacramento, CA; and his son Jameson Stephenson of Roseville, CA. He is also survived by three grandchildren; his brother Andy and niece Macy of Cornelius, NC; his sister-in-law Trudy and nephew Shaun of Winter Haven.

In lieu of flowers donations can be made to Theatre Winter Haven, 210 Cypress Gardens Blvd SW, Winter Haven, FL 33880; or by calling (863) 294-7469.