Following her worldwide promotional tour in support of her previous album The Memory of Trees (1995), Enya began selecting tracks for a compilation album in early 1997, as her recording contract with WEA permitted her to do so.

Paint the Sky with Stars received positive reviews from critics and was a commercial success, reaching number 4 in the United Kingdom and number 30 on the Billboard 200 in the United States.

In the latter territory, the album continued to sell over the next eight years, reaching four million copies shipped in 2005.

[2][3] Paint the Sky with Stars received universal acclaim from music critics.

Stephen Thomas Erlewine from AllMusic rated the album five stars out of five and says that Paint the Sky with Stars: The Best of Enya is an excellent 16-song overview of Enya's career, containing 14 selections from The Celts, Watermark, Shepherd Moons, and The Memory of Trees, including "Caribbean Blue", "Anywhere Is", "Marble Halls", "Book of Days" and, of course, "Orinoco Flow"—as well as two previously unreleased songs ("Only If...", "Paint the Sky with Stars") that fit comfortably with her past work.