Ironically, Crystal Waters hadn’t even heard of house music until she composed the song that would become one of the greatest house tracks of all time.
It was the late ’80s when the singer – who came from a musical family in her native New Jersey – was, according to her own account (from a 2017 interview with the Ibiza party brand and the Glitterbox label), “does more of a Sade type of thing; I was doing a jazz R&B type thing.
Waters would not abandon this style on his hit, but rather fuse his jazz-influenced delivery with a genre then exploding out of the underground in cities like New York and Chicago. Waters actually helped this new sound — house music — with his mainstream ’90s crossover, and earned himself a massive and lasting club hit in the process.
The gears of fate clicked when Waters, then living in Washington DC, crossed paths with Baltimore production trio The Basement Boys. The band asked Waters to write a demo for dance diva Ultra Naté. What Waters came up with so impressed The Basement Boys that they told her she should just work with them to record and release the song herself.
“When I met them, I gave them my demo and they loved my songwriting,” Waters explained in this 2017 interview with Glitterbox. “They offered to shop the demo,” but, she added, “they wanted me to keep my same style on those dance beats. It was my first introduction to house music.
The Basement Boys’ production for the song that would become “Gypsy Woman (She’s Homeless)” consisted of a thick bassline, over which they layered thick strings, random beats, and the song’s signature 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 would eventually come up with alternative (and more conceptually concrete) lyrics.
But she “couldn’t find any lyrics that matched the short little syllable”, and so the scat-style improvisational 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 a character’s perspective. Racking her brains for inspiration, she remembered a kind of fabulous woman she had seen singing on a street corner in downtown DC.
“She would dress in black, make up all over her face, and she would sing these gospel songs with her hat on in the street asking for money,” Waters recalled. “And I was like, ‘This woman has money, she looks good,’ and I had an attitude about it.”
“And then the local paper did a whole story about her,” Waters continued, “saying she had just lost her retail job and felt like if she was going to ask for help money to people, she was going to show some respect and keep herself neat and clean, so that changed my whole idea of homelessness and how it could be you and me.
Waters said that while reading this newspaper article about this homeless street singer, the rest of the song’s lyrics came to mind, and the song’s titular “gypsy” was born. “She’s 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 hook “the da dee, la da da”.
“Gypsy Woman (She’s Homeless)” was released on April 3, 1991 via Mercury Records and quickly soared to the top of Billboard‘s Dance Clubs Songs list, where it held the top spot 30 years ago today (May 26). The song also became Waters’ only top 10 hit on the Hot 100, reaching No. 8 on July 6, 1991.
Throughout music history, Waters was disappointed that the song’s socially conscious lyrics went over the heads of carefree clubgoers and so set foot to demand that label execs add “(She’s Homeless)” in the title of the song. But for a track about such a serious issue, the song’s serious verve and bounce are arguably what made it a highlight in house history, one included on myriad “best of” lists. house songs of all time”.
Billboard too ranked Waters at No. 39 on our list of the best Dance Club Songs artists of all time. The singer also recently made headlines and chart moves in February, when her 1994 hit, “100% Pure Love”, reached No. 9 on the Dance/Electronic Digital Song Sales, – reappearing for the first time in a decade, after being featured in a January episode of RuPaul’s Drag Race.
“Gypsy Woman (She’s Homeless)” also took on new life when Trey Songz sampled it for his 2017 track “1×1” (listen closely and you can hear the keyboards in the pre-chorus.) During this time dance producer Mija did her 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 demonstrating further how the song really is a fusion of house and jazz.
“It was a great combination of influences,” said Thomas Davis of the Basement Boys. Billboard in 1991. “Crystal brings a jazz and blues background to his music, which blended well with our various ideas.” 30 years later, this particular blend is now timeless.