Born in Cleveland's Fairfax neighborhood, near East 85th Street and Quincy Avenue, to Naomi Womack and Friendly Womack, Bobby was the third of five brothers. Friendly Jr. and Curtis were the older brothers, Harry and Cecil were his younger brothers. They all grew up in the Cleveland slums, so poor that the family would fish pig snouts out of the local supermarket's trash. He had to share a bed with his brothers.

Womack opened up about his frequent drug use in his memoirs, Midnight Mover. Womack said he began using cocaine sometime in the late 1960s. He had become close friends with Sly Stone, and was an enthusiastic participant in Stone's infamous drug binges. Womack told Rolling Stone in 1984:  "I was really off into the drugs. Blowing as much coke as I could blow. And drinking. And smoking weed and taking pills. Doing that all day, staying up seven, eight days. Me and Sly [Stone] were running partners."  His cocaine use turned into an addiction by the late 1970s. Womack partially blamed his habit for his son Truth's death. Throughout most of the 1980s, Womack struggled with drug addiction. In the early 1980s his career slowed down partially due to his drug usage. At the end of the 1980s, he went into a rehabilitation center to get over his cocaine addiction, which he said he conquered.  Womack survived prostate cancer. A series of health problems would follow, including diabetes, pneumonia, colon cancer and the early signs of Alzheimer's disease.  Womack developed diabetes in his later years. It was revealed in March that Womack was diagnosed with colon cancer after Bootsy Collins reported it on his Facebook page. Womack announced afterwards that he was to undergo cancer surgery. On May 24, 2012, it was announced that Womack's surgery to remove a tumor from his colon was successful and he was declared cancer free. On January 1, 2013, Womack admitted that he struggled to remember his songs and other people's names, and later he was diagnosed with early stages of Alzheimer's disease.

Other than prostate cancer did he have any other health conditions?
A series of health problems would follow, including diabetes, pneumonia, colon cancer and the early signs of Alzheimer's disease.