Accompanied by an electric piano, beatbox, guitars, synthesizers, Arabian-inspired riffs and Gregorian chants, "Cry Me a River" is a pop and R&B song about a brokenhearted man who moves on from his past.

"Cry Me a River" received acclaim from music critics, who praised Timbaland's production while calling it a standout track on Justified.

Filmmaker Francis Lawrence directed the music video for "Cry Me a River" at 24860 Pacific Coast Hwy in Malibu, California.

The phrase "cry me a river" is an idiom used sarcastically to express a lack of sympathy for someone's excessive complaints or self-pity, implying that their grievances are exaggerated or unworthy of attention.

Timberlake arranged the vocals and was a backup singer alongside Timbaland, Marsha Ambrosius, Tye Tribbett and Greater Anointing.

[17] Following its release, there was media speculation that Spears had written a song as a response to "Cry Me a River";[4] she denied the rumors, explaining, "You know, it's funny.

"[20] "Cry Me a River" is a pop[24][25] and R&B song[26] with instrumentation that features clavinet, guitars,[2][22] beatboxing,[23] synthesizers, Arabian-inspired riffs and Gregorian chants.

[22] Billboard magazine critics called "Cry Me a River" a bittersweet song, in which the singer's "familiar tenor belting" is tempered with a soulful falsetto and a "convincingly aggressive rock-spiked baritone" rasp.

[7][22] Tanya L. Edwards of MTV News observed that Timberlake was lied to and wronged, and said this is demonstrated by the lyrics: "You don't have to say whatcha did / I already know, I found out from him / Now there's just no chance.

"[35] Slant Magazine's Sal Cinquemani called Timberlake's 2007 single "What Goes Around... Comes Around" an ostensible sequel to "Cry Me a River" both lyrically and musically.

[39] 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.

[31] 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.

[30] 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.

"[43] VH1's Emily Exton wrote, "By stretching the boundaries of pop–and fusing it with notes of R&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.

Lawrence revealed that executives of Jive Records were also nervous about other aspects of the video, such as Timberlake's representation of a voyeur and the tone of some scenes he was portraying with a girl.

"That's the thing I liked most about this project, was that he was coming into it with a super clean-cut image with 'N Sync and he's such a nice guy and so handsome and what I was into doing was making him be a bit scary.

[84] The video begins with a blonde woman, played by model and actress Lauren Hastings (portraying Spears[85]), walking out of her house hand-in-hand with an unidentified man.

"[88] According to Virginia Heffernan of The New York Times, Timberlake channels the character Neo from The Matrix film series, "pacing anxiously around wet and metallic interiors".

He added, "The "Cry Me a River" video served a dual purpose for Timberlake: to court controversy, and to make its star seem more grown-up.

[97] He again performed the song at the 13th annual Billboard Music Awards, held on December 9, 2002, at the MGM Grand Garden Arena in Las Vegas.

Timberlake performed "Cry Me a River" on a promotional concert held at House of Blues in West Hollywood, California on June 17, 2003.

[100] He performed a rock-inspired version of the song on Saturday Night Live on October 11, 2003;[101] and it was fourteenth on the set list of his second worldwide tour, FutureSex/LoveShow (2007).

[102] During his world tour in Zürich, Switzerland, in August 2007, Timberlake performed "Cry Me a River" and segued into the chorus of "Rehab" by Amy Winehouse.

[110] American singer-songwriter Taylor Swift performed a cover of "Cry Me a River" in Memphis, Tennessee, during the Speak Now World Tour (2011–12).

[117] In January 2013, American singer Selena Gomez performed an acoustic version of "Cry Me a River" at the UNICEF charity concert in New York City.

[118] In February 2015, Scottish synthpop band Chvrches performed a cover of "Cry Me a River" on BBC Radio 1's Live Lounge.

In May 2020, Democratic presidential nominee Joe Biden released a campaign ad which took aim at Donald Trump for complaining in a 2020 interview about being "treated worse" by the media than any other president instead of focusing on the ongoing COVID-19 pandemic.

[120] "[The song] is the universal symbol of the bad celebrity break-up – more powerful than a stack of Angelina vs. Aniston tabloid covers, more effective than an official statement mailed to People magazine."

"Cry Me a River" marked the first collaboration between Timberlake and Timbaland, and its critical and commercial success started "one of the most forward-thinking star-producer duos in pop music", as described by Variety's author Andrew Barker.

"[125] Rosalía samples the chorus from "Cry Me a River" for her song "Bagdad" on her album El mal querer (2018), featuring a Barcelona children's choir.