Meaning Behind the Breakup Song “Cry Me a River” by Justin Timberlake

It’s the song that made Justin Timberlake a solo star. It’s also the song that cemented his very public breakup with former Disney star and then-current pop star Britney Spears. Pushing her down and catapulting Timberlake, formerly of *NSYNC, the track is one of the most historic breakup songs ever.

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Yes, it’s “Cry Me a River.” Here, we dive into the history and meaning of the song, which Timberlake recorded with longtime collaborator and producer Timbaland.

[RELATED: The 20 Best Quotes From Justin Timberlake]


Timberlake’s song was released on his debut 2002 solo album, Justified, which also included hits like “Rock Your Body” and “Señorita.” The record came at the height of the bubblegum pop era, which included the likes of boy bands (Backstreet Boys, *NSYNC, 98 Degrees) and starlets like Spears, Christina Aguilera and Jessica Simpson.

The song, which won the 2004 Grammy Award for Best Male Pop Vocal Performance, was seemingly aimed at Spears. Previously, Timberlake and Spears, both former Mickey Mouse Club participants, had dated. They also made denim famous again. But when rumors of Spears’ infidelity surfaced, the two split.

The Lyrics

The song opens with the smooth singer lamenting,

You were my sun
You were my earth
But you didn’t know all the ways I loved you, no
So you took a chance
And made other plans
But I bet you didn’t think that they would come crashing down, no

You don’t have to say, what you did
I already know, I found out from him
Now there’s just no chance
For you and me
There’ll never be
And don’t it make you sad about it?

You told me you love me
Why did you leave me all alone?
Now you tell me you need me
When you call me on the phone
Girl, I refuse
You must have me confused with some other guy
The bridges were burned
Now it’s your turn, to cry


There was no bigger pop star at the turn of the 21st century than Britney. And while coveted by many, she and Timberlake seemed to have a good thing going. Until there were rumors about her and Limp Bizkit frontman Fred Durst. Not long after, there were also rumors about Spears and former backup dancer Kevin Federline.

After “Cry Me a River” had been released, Timberlake spoke with MTV News. “I’m not going to specifically say if any song is about anybody,” he told the publication. “I will say writing a couple of songs on the record helped me deal with a couple of things. To me songs are songs. They can stem from things that completely happened to you personally or they can stem from ideas that you think could happen to you.”

But in 2011, he changed his tune, saying that the song was written after he and Spears got into a phone argument. “I was on a phone call that was not the most enjoyable phone call,” he said at the time. “I walked into the studio and he [Timbaland] could tell I was visibly angry.”

Acclaimed producer Timbaland also was interviewed in that same 2011 article. “I was like, ‘Man, don’t worry about it’ and he was like, ‘I can’t believe she did that to me’ and he was like, ‘You were my sun, you were my earth,'” Timbaland recalled.

A year later, Spears released the song “Everytime,” and while some wondered if it was a response to Timberlake’s breakup diss track, Spears set the record straight to MTV News. “You know, it’s funny. I read that I wrote this song and I wrote these lyrics and that’s not my style,” she said. “I would never do that.” Yet, that song’s co-writer Annet Artani, said that it was indeed a response to the former *NSYNC star.

Doubling Down?

Seeing the success his Spears diss track had, Timberlake, who later had a rocky relationship with another pop star Janet Jackson, doubled down on the move, releasing his song, “What Goes Around… Comes Around” on his 2006 LP, FutureSex/LoveSounds. That project was also produced by Timbaland.

While Timberlake has said the 2006 song was inspired by the experience of a friend—not of his with Spears—it’s hard for many to believe this is the case. Especially given the 2002 single and the easy connection between the two pop hits.

On this song, he sings,

Is this the way it’s really going down?
Is this how we say goodbye?
Should have known better when you came around
That you were gonna make me cry
It’s breaking my heart to watch you run around
‘Cause I know that you’re living a lie
But that’s okay, baby, ’cause in time you will find

What goes around, goes around, goes around
Comes all the way back around
What goes around, goes around, goes around
Comes all the way back around
What goes around, goes around, goes around
Comes all the way back around
What goes around, goes around, goes around
Comes all the way back around, yeah

Final Thoughts

While both these songs are immaculate pop tracks, they are also indicative of the way Hollywood and fame often work. In one sense, they turn pain into power. In another, they push someone down for the sake of another’s rise. Polarizing, at times hard to swallow.

Photo by Paul Marotta/Getty Images for Berklee

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