"Cry Me a River" received acclaim from music critics. Jane Stevenson of Jam! and Sal Cinquemani of "Slant Magazine" called it a standout track on "Justified". Stephen Thomas Erlewine of AllMusic selected the song as a highlight in his review of "Justified". Peter Robinson of "NME" described it as a "twisted epic" and "an acidic, filthy little song teeming with spite and retribution, with Timbaland's pounding." "Rolling Stone"s Ben Ratliff viewed his production of "Cry Me a River" as exceptional. Denise Boyd of BBC Music felt that the song's lyrics play as large a role as Timbaland's production, unlike other songs on "Justified". David Browne of "Entertainment Weekly" concluded that the song is "a genuine stunner" that should leave Timberlake's fellow 'N Syncers concerned that he truly may not need them any more. John Mitchell of MTV News called "Cry Me a River" and "What Goes Around... Comes Around" "kiss-off songs", with Timberlake's revenge on Spears present throughout the lyrics. Idolator staff opined it is the sound of an artist who is "relishing ripping up people's perceptions of him as a sweet-natured teen heartthrob." VH1's Emily Exton wrote, "By stretching the boundaries of pop–and fusing it with notes of R&amp;B, lots of electric goodness, and haunting choral vocals–Timberlake’s kiss-off song instantly becomes more poignant, a pointed reaction to the hurt he’s experienced by someone he once loved." According to "Complex", the song "made people completely forget about 'N Sync and start asking what Timberlake would do next." The single won a Grammy Award for Best Male Pop Vocal Performance at the 2004 award ceremony. It was nominated for Song of the Year at the 2003 MTV Europe Music Awards.