The gears of fate went into motion when Waters, who was then living in Washington D.C., crossed paths with Baltimore production trio The Basement Boys. The group asked Waters to write a demo for dance diva Ultra Naté. What Waters came up with impressed The Basement Boys so thoroughly that they told her that she should just work with them to record and release the song herself.
"When I met them, I handed them my demo and they loved my songwriting," Waters explained in that 2017 Glitterbox interview. "They offered to shop the demo around," but, she added, "they wanted me to keep my same style over these dance beats. That was my first introduction to house music."
The Basement Boys' production for the song that would become "Gypsy Woman (She's Homeless)" was composed of a thick bassline, over which they'd had layered chunky strings, shuffling beats and the song's iconic keyboard. It was groovy, hypnotic, sophisticated and fun. As Waters worked out the words for the track, she inserted "la da dee la da da" as a placeholder in the hook, anticipating that she'd eventually come up with alternative (and more conceptually concrete) lyrics.
But she "couldn't find any lyrics that fit the short little syllable," and so the improvisational, scat style vocals that would become the song's calling card remained. During this writing process, Waters also felt it would be helpful for her to write from the perspective of a character. Racking her brain for inspiration, she recalled a sort of fabulous woman she'd seen singing on a street corner in downtown D.C.
"She would dress in all black, full face of makeup and she would sing these gospel songs with her hat out on the street asking for money," Waters recalled. "And I was like, 'This woman has money, she looks fine,' and I had an attitude about it."
"And then the local paper did a whole article on her," Waters continued, "saying that she just lost her job in retail and she felt like if she was going to ask people for money, she was going to show some respect and keep herself neat and clean. So that changed my whole idea about homelessness and how it could be you and me."
Waters said that upon reading this newspaper article about this homeless street singer, the rest of the song's lyrics just came to her, and the song's titular "gypsy woman" was born. "She's just like you and me/ But she's homeless, she's homeless/ As she stands there singing for money," Waters laments, before accentuating the chorus with that "la da dee, la da da" hook.
"Gypsy Woman (She's Homeless)" dropped on April 3, 1991 via Mercury Records and swiftly ascended to the top of Billboard's Dance Clubs Songs list, where it sat in the No. 1 position 30 years ago today (May 26). The song also became Waters’ only top 10 on the Hot 100, reaching No. 8 on July 6, 1991.
As music history lore goes, Waters was bummed that the song's socially conscious lyrics were going over the heads of happy-go-lucky clubgoers and thus put her foot down to demand that label execs add “(She’s Homeless)” to the song’s title. But for a track regarding such a serious issue, the song's serious verve and bounce are arguably what's made it a highlight of house history, one included on myriad "best house tracks of all time" lists.
Billboard too listed Waters at No. 39 on our list of the top Dance Club Songs artists of all time. The singer also made recent headlines and chart moves in February, when her 1994 hit, "100% Pure Love" hit No. 9 on Dance/Electronic Digital Song Sales, -- reappearing for the first time in a decade, after it was featured in a January episode of RuPaul's Drag Race.
"Gypsy Woman (She's Homeless)" also got new life when Trey Songz sampled it for his 2017 track ""1x1" (listen closely and you can hear the keyboards in the pre-chorus.) Meanwhile dance producer Mija did her own stripped down version in 2019, the same year Coldplay (and a string section) covered the song for a BBC Radio 1 performance, with Chris Martin's piano playing and singing further demonstrating how much the song really is a fusion of house and jazz.
"It was a great combination of influences," The Basement Boys' Thomas Davis told Billboard in 1991. "Crystal brings a background of jazz and blues to her music, which blended well with our various ideas." 30 years later, that particular blend is now timeless.