Cry Me a River

Justin wrote this song about Britney Spears. In the song, the relationship goes bad because the girl cheated, and to get even, the boy makes sure the girl finds out he's moved on with his life. The girl gets upset, and "cries a river" because she screwed up and lost the boy forever. The track was written and recorded following a heated phone conversation between Timberlake and Spears. During a E! True Hollywood Story special about Timbaland, the producer explained, "He went to a concert and saw Britney, and Britney talked about him in the show and he was pissed." Timberlake added, "I was on a phone call that was not the most enjoyable phone call. I walked into the studio and he (Timbaland) could tell I was visibly angry." The singer then poured out his furious feelings in the song.

Timberlake and Spears were in Disney's Mickey Mouse Club together when they were younger. They dated for 2 1/2 years before breaking up in 2002. Justin claimed she cheated on him with her choreographer, Wade Robson. In 2003, Britney said Justin was the only guy she ever had sex with, and she did it because she thought they would get married someday. She described their breakup as the most painful thing she's ever experienced.

In the video, Timberlake uses a video camera to tape him getting hot and heavy with another girl. When his girlfriend (who is played by an actress that looks very much like Britney Spears) comes in, he sets it up so she will see the tape. The video leaves little doubt that it is a message to Spears. The Britney look-a-like was played by actress Lauren Hastings. She recalled to Q magazine June 2009: "I went for a casting and they asked if I'd be comfortable 'making out' with Justin. I said Yes! I had a huge crush on him and once dated a guy just because he looked like him." She added: "The video was shot over three days in Malibu, next to Cher's house. I was so nervous when I got to finally meet Justin and he told me he'd handpicked me because I looked like Britney. Of course I found him attractive, but I was professional and didn't tell him and treated it like any other job." Hastings concluded: "It led to a recurring role in TV drama The O'Keefes along with a Maroon 5 video and commercials for Tampax, Nike and a deodorant campaign with Ben Affleck. There have been no downsides to it."