The niece of a prominent member of MFSB, who helped create dance music as it exists today by transforming New Philly Soul in Disco, Crystal Waters was no strangers to the world of dance , when a co-worker asked her if she would be a backup singer for her cousin's studio. On a whim Waters went down to the studios and got hired as a backup, but quickly began to write songs, as some of the producers enjoyed her Jazz and Blues background to mix with their House Music compositions. Together with Neal Conway, Waters would write a song about a homeless woman she would walk by everyday, that she was annoyed by since the woman was well dressed and mannered, and Waters found it hard to believe that the woman cojuld not find a job. Waters, would later come to find that the woman was indeed homeless as her job was eliminated and she was on her last leg aksing for charity. The woman did not think it appropriate to ask for money on the streets and not have the decency to be well dressed and mannered, and the lady's story shook Waters who penned the lyrics about the homeless woman's struggle.
"Gypsy Woman" was initially made as a demo sung by Waters herself, to be a single for dance singer Ultra Nate', but when her production company heard Waters performance, she was signed on the spot. Together with the "Basement Boys," the song would become the lead single for her debut album, "Surprise". The song became an instant hit, and Waters popularity soared, but Crystal was upset that people became so enamored by the song they missed the point of the lyrics. She would order the label to add "She's Homeless" to the single's cover to drive attention to the homeless problem the inspiration of the song was going through.
Gypsy Woman would find continued success when it got remixed for the Red Hot Organization's Red Hot + Dance AIDS fundraiser album, by Joey Negro who would later go by the name Jakatta, kickstarting his career in dance. The song became an instant House classic, and fuel Waters career through the 90's and into the 2000's. The song itself would get sampled by many to create extended hits, including T.I.'s "Why You Wanna". The song gave Dance music the credibility of being as socially conscious and Hip-Hop, and marked the more electronic sound that House was evolving into during the 90's, and is widely considered one of the greatest and most infectious dance songs of all time.