Michael Wayne Calloway

Michael Wayne Calloway, of Louisville, Kentucky, drifted into eternal rest in the late hours of January 28, 2026, with his daughter by his side. He was born on April 20, 1957 to Marie Calloway and Robert Lee Harpool.

Michael followed his heart with conviction from an early age. He married his high school sweetheart, Dywanna Wimberly, and together they welcomed their daughter, Tabatha Wright.

A man of many talents, Michael founded Calloway Construction Company early in his adulthood, earning respect for his craftsmanship and dedication. After years of independent work, he expanded his skills and obtained his commercial driver’s license, a path that allowed him to provide for his family while traveling the world. In his early years, he also briefly served in the military, showing the same sense of duty that guided him throughout his life.

Among the many things that brought him joy, riding motorcycles was his greatest passion. The open road, the freedom of the ride, and the peace he found behind the handlebars were central to his spirit.

Michael was preceded in death by his mother Marie Calloway; his biological father Robert Harpool; his father Irvin Calloway, his stepmother Alyce Calloway, and his eldest brother LeVern McDonald. He leaves to cherish his memory his daughter Tabatha Wright; Shaun Conley Sr. ,whom he loved and raised as his own son; his step-daughter Monique McGinnis; his grandchildren Alexis Ashby and Thomas Pendergrass; his brothers Kim Calloway, Sean Calloway, Reggie Calloway, Vincent Calloway, and Greg Calloway; chosen grandchildren Breon Conley, Unique Conley, Shaun Conley Jr, India Conley, Tiara Conley, and Catrina Conley; a host of nieces and nephews, cousins, life long friends, and his longtime companion, Joyce Ware. Those who knew Michael will remember his adventurous spirit, his love for the open road, the quiet pride he carried for the life he built, and the family he cherished.

Though he has taken his final ride, his memory will forever live in the hearts of those who loved him.

Visitation will be on Thursday, February 12, 2026 from 10:00 a.m. until 12:00 p.m. at Newcomer Cremations, Funerals & Receptions, Southwest Louisville Chapel, 10304 Dixie Highway. A celebration of his life will be held on Thursday at 12:00 p.m. at the funeral home followed by entombment at Evergreen Cemetery in Louisville, Kentucky. The family would like to invite family and friends to a repass at First Virginia Baptist Church, 3601 Virginia Avenue, Louisville, Kentucky, 40211, immediately following the graveside service.