Haddaway was born in Trinidad and Tobago in 1965. His mother was a nurse and his father was a marine biologist. His parents separated in the early 1970s and Haddaway first lived with his father in Europe, then with his mother in America. He was raised in Chicago and moved to the Washington, DC metropolitan area at the age of 9. Listening to Louis Armstrong encouraged Haddaway to learn how to play trumpet at the age of 14. He attended Meade Senior High School in Fort Meade, Maryland, where he was a member of the marching band, which eventually resulted in him forming his first group titled “Chances”. In 1987, Haddaway enrolled in medical school, but dropped out due to lack of excitement and moved to Cologne, West Germany, where he mostly worked in bars. Later, he formed his own company called “Energy”, which was involved in organizing fashion shows and photo shoot.