Most dance songs take place in the club or some other place of revelry, but this song is set on a city street, where a homeless woman in full makeup is singing for money. It's about a real person. In a Songfacts interview with Crystal Waters, she told the story:
"I was in Washington, D.C. and she used to stand in front of the Mayflower Hotel on Connecticut Avenue. She was dressed all in black and a full face of makeup, singing gospel songs, and I used to walk by her like once a week. I'd be like, 'There's nothing wrong with her, she needs to go get a job.' I had a really bad attitude about her. And then the local city paper did an article on her and she said she had just lost her job in retail and she feels like if she was going to ask someone for money she could at least be presentable and look presentable.
The story changed my whole attitude about homelessness, how it could have been anybody. Last week she had a job, this week she didn't. She was just like you and me - like what I said in the song. So, that whole incident really changed my attitude about homelessness and that's what I wrote the song about."
The song has a wordless chorus, repeating "la da dee, la da da" over and over. There was a practical reason for this: When Waters came up with the vocal melody, the syllables were too short to use actual words. This section represents what the gypsy woman is singing.
There is no mention of gypsies in this song, but there was originally, which is why the song got titled "Gypsy Woman." When it was first released, it was labelled "Gypsy Woman (La Da Dee La Da Da)" or "Gypsy Woman (La Da Dee)" depending on the country. The song's message seemed to be getting lost, so it was re-titled "Gypsy Woman (She's Homeless)" on later pressings, which became the song's official title.
Speaking of gypsies, they're kind of hard to classify as an ethnicity, per se. They are originally from India, but wandered up into all of Europe. Nomadic by tradition, they settled into various pockets of culture and are variously called Roma, Romani, Sinta, Kale, and Bohemians. The name comes from the mistaken belief that they were from Egypt.
This was produced by the Baltimore team The Basement Boys, who were Neal Conway, Teddy Douglas, Jay Steinhour and Thomas Davis. Conway wrote the track, did the string arrangement, and played the distinctive Leslie organ riff.
The track was written for the singer Ultra Naté, when Waters recorded the demo, it was clear that she should sing it. Waters wasn't looking to become a singer: She went to university studying business and computer science, and started a career working as a computer tech in Washington, D.C. She got into the music business by landing a gig as a backup singer for Freddy Cole, which led her to the Basement Boys production team. She had been writing poetry for a while, and found she had a knack for melody - not surprising considering her musical family (her great aunt, Ethel Waters, was a huge singing star in the 1930s). When "Gypsy Woman" took off, she was able to quit her day job and pursue music full time.
The song doesn't contain any samples, but has been sampled a number of times, including on the 2006 T.I. hit "Why You Wanna." Other songs to sample it include:
"1x1" by Trey Songz (2017) "Of All Things" by G-Eazy (2015) "Brand New Me Part 2" by Alicia Keys (2013) "Walking" by Mary Mary (2010)
Dance music was all over pop radio in 1991, with acts like C+C Music Factory, PM Dawn and The KLF having their heydays. There were also a number of female vocalists who found success, with Waters, Cathy Dennis, Corina and Karyn White joining established stars like Janet Jackson and Madonna on the charts. Many of these acts faded from view as hip-hop and grunge took hold, but Waters stayed relevant. Her second album, Storyteller, wasn't released until 1994, but it contained the hit "100% Pure Love," which reached #11 on the Hot 100. In the '00s, she was part of two international hits: "Destination Calabria" and "My Time." In 2017, she had a #1 Dance hit with her Hifi Sean collaboration, "Testify."
The video was directed by Mark Pellington, whose credits include "Jeremy" by Pearl Jam and "Skyscraper" by Demi Lovato. Set against a white background, Waters appears in a business suit - not the typical dress code of a dance diva.
"I'm not the type of person who likes to show a lot of skin, so back then I used to love to wear suits and jackets and jeans," she told Songfacts. "At first, they wanted to put me in glittery long gowns and I was like, 'No. No disco diva here.'"
The video has some striking imagery, including the gypsy woman behind a mask and a spinning umbrella emblazoned with the "la da dee, la da da" refrain.
In our interview with Pellington, he said: "I love that song. She was lovely - she showed up, shot it, and did it. In those days, I'd just kind of show up and do it."
This song was famously parodied in the TV comedy variety series In Living Color, which often re-created popular music videos in bizarre fashion. This one, with Kim Wayans playing Waters, was called "My Songs Are Mindless," and pictured Waters getting her hooks from TV shows, turning this song into a Fred Flintstone tribute with "yabba dabba doo" in place of the "la da dee, la da da" part.
It's pretty harsh, with Wayans delivering lines like "I'm gonna be a rhythmic star with little talent" and laughing all the way to the bank. "I don't like it. Nobody likes to be made fun of," Waters said in her 2017 Songfacts interview. "Marlon Wayans sent a message to my daughter and said something about how it's the highest form of flattery and all that stuff, but now when people think of it, they only think of that."