Written by Neal Conway and Waters, the song was released on April 3, 1991 by Mercury Records, as the lead single from the album.

Outside of the United States, "Gypsy Woman (She's Homeless)" topped the charts in Italy, the Netherlands, Spain, and Switzerland, as well as on the Eurochart Hot 100.

"I said to myself there must be someone singing it, and I thought of this woman ... she used to stand downtown on the corners, and she was dressed in all black," she told the Glitterbox Radio Show in 2017.

[6]Even though the sound was a huge dance hit, Crystal Waters wanted people to listen to the lyrics about homelessness.

In the United Kingdom, "Gypsy Woman" debuted at number three on the UK Singles Chart on May 12, 1991 – for the week ending date May 18, 1991.

In the rest of Europe, "Gypsy Woman" peaked at number one also in Belgium, Italy, the Netherlands, Spain and Switzerland.

"[8] Larry Flick from Billboard remarked that the "inspired deep house dish" has already begun to explode at club level, "thanks to Waters' unique vocal and a hypnotic hook and groove crafted by hot production team the Basement Boys.

"[11] Marisa Fox from Entertainment Weekly constated, "You just can't escape this summer's runaway hit song, the jazz-house hybrid 'Gypsy Woman' [...].

"[15] Alan Jones from Music Week wrote that the "insidious" chorus "can be a little wearing after a while, but there's enough promise in the verses, both melodically and lyrically to suggest that Waters can be a bright new star.

[17] James Hamilton from the Record Mirror Dance Update stated that "this Basement Boys produced strange haunting plaintive girl chanted and keyboards jabbed frisky Italo-type canterer has a madly catchy "la da dee, la de dah" chorus".

He commented further, "A rather vapid lyric reduction of the sorrow and tragedy of homelessness [...] was nevertheless a rare bright spot of originality and blessed simplicity amid a '91-long plague of Identikit house records and overwrought remixes.

"[19] Scott Poulson-Bryant from Spin wrote that "with its nursery-rhymish hook and accessible cultural concern, this hypnotically danceable track has insinuated itself into the pop consciousness with an almost dreamy forcefulness".

[20] The accompanying music video for "Gypsy Woman" was directed by American film director, writer, and producer Mark Pellington.

Occasionally a "gypsy woman", wearing a theater mask and gold gloves, can be seen holding a handheld mirror while putting on lipstick, dancing under a street light or lying on a park bench.

[22] AllMusic editor Alex Henderson wrote that it "made it clear that house music could be as socially aware as rap".

He described it as a "wildly infectious treasure", noting further that it has a "poignant and moving reflection on a homeless woman's struggle that makes its point without preaching.

[24] Music critic of Spin, Jonathan Bernstein said in 1994, "So insidious, so remorseless a summer smash was Crystal Water's "Gypsy Woman" that several defense attorneys got their rooftop sniper clients off the hook by pointing to the subliminal qualities of the song's sinister la-da-di's.

"[25] Slant Magazine ranked it 10th in its "100 Greatest Dance Songs" list in 2006, writing: Crystal Waters's thick-ankled house anthem takes the baton of social consciousness from the likes of Machine.

And just as "There But for the Grace of God Go I" makes its pungent point clear through its musical prickliness, "Gypsy Woman (She's Homeless)" sets its portrait of a crusty, haphazardly made-up bag lady dementedly begging on street corners to the Basement Boys's unforgivingly brutish thump.

As Crystal's first-person protagonist stands there, singing for money, her lah-dah-dee's are nearly buried in the brackish clatter, subtly expressing the heartbreaking fact that the plight of the homeless often falls on completely deaf (sometimes ringing) ears.

Waters's astringent message was delivered to a club clientele that had become too pathologically petrified of breaking a sweat, canting a weave, or otherwise allowing themselves to get ugly to actually set foot on any dance floor not shaped like a fashion runway.

[3] On October 25, 1991, Rumi Shishido released a cover version in Japanese as her sixth single, titled "Otokonoko ga Naichau Nante (La Da Dee)".

In November 2024, Peruvian singer La Tigresa del Oriente released a cover version of "Gypsy Woman".