The Very Best of Macy Gray is the first greatest hits album by American singer and songwriter Macy Gray.

It contains all singles from Gray's first three studio albums, as well as two previously unreleased tracks (the single "Love Is Gonna Get You" and a cover of Aerosmith's 1975 song "Walk This Way"), three album tracks, three remixes, and the 2000 single "Demons", a collaboration with Fatboy Slim.

The album peaked at number 36 on the UK Albums Chart and charted moderately in other European countries.

On December 1, 2008, the album was reissued in the United Kingdom including "Winter Wonderland", which first appeared as a B-side to "Sexual Revolution" and was featured in the Marks & Spencer Christmas ads.

A few weeks later, the song reached number 76 on the UK Singles Chart.