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With ‘Cry Me a River,’ Justin Timberlake Said Goodbye to Britney and His Boy-Band Image

On his 40th birthday, we look back at the singer’s breakthrough single, a dark, brilliant ballad about pretending to get over your ex

Guys, especially when they’re young, have a tough time being dumped. It bruises their ego, challenges their masculinity, makes them have to get in touch with feelings they’d rather ignore. For most of us, our options for responding are pretty limited. We can sulk, get sad, get angry, pretend like it doesn’t bother us, but none of them are sufficient reactions if you’re really heartbroken. However, if you’re Justin Timberlake — and you’re getting over rejection and trying to start a solo career — well, the possibilities are a little more limitless. 

Nearly 20 years later, “Cry Me a River” remains a stunner. At the time, he swore it wasn’t about his ex, but we all knew that wasn’t true. It had to be about Britney — the guy even hired an actress for the video who looked just like her. But the real reason it had to be about Britney was that the song was too good — too pointed in its anger — to be a work of fiction. Most of us can only fantasize about the perfect kiss-off we’d deliver to the person who hurt us. Timberlake expressed it in such a way that, after all this time, it still feels weirdly intimate — like we’re eavesdropping on something that we shouldn’t be hearing. But the song’s so great you never want to stop listening.

Since before he was a teenager, Timberlake has been in showbiz. He was on Star Search when he was 10. Not that long after, he was part of The All-New Mickey Mouse Club, and before his 17th birthday, he and his group NSYNC had released their self-titled debut, which peaked at No. 2 on the charts. The boy band released three records, and a Christmas album, and produced six Top 10 singles. But even though there were five guys in the group, Timberlake always sorta stood out. He had the most charisma and the best looks. And after their 2001 album Celebrity, he decided it was time to move on. “I was growing out of it,” he said later. “I felt like I cared more about the music than some of the other people in the group. And I felt like I had other music I wanted to make and that I needed to follow my heart.”

The boy-band era was known for its immaculate pop songs and inoffensively cute singers. Timberlake was both of that ilk and wanting to break free of it, probably in part because edgier artists like Eminem wouldn’t stop making fun of NSYNC. But what tied him to his past was the fact that he’d been dating Britney Spears, whom he’d known since their days on Mickey Mouse Club, for several years. (“I was in love with her from the start,” Timberlake once recalled. “I was infatuated with her from the moment I saw her.”) When they were a couple, though, she was the bigger star. Yes, NSYNC were huge, but she was a massive solo artist, flaunting a sexual confidence in hits like “…Baby One More Time” that Timberlake’s squeaky-clean crew couldn’t match. So when the couple broke up in early 2002, it felt — to the public, anyway — that she had cast him aside. Her career was going great — what was this boy-band kid going to do next?

The seeds for Timberlake’s first solo album, Justified, had been sown on Celebrity, where the singer first teamed up with the Neptunes, the hip-hop production duo made up of Pharrell Williams and Chad Hugo. Their collaboration, “Girlfriend,” was NSYNC’s last Top 10 hit, and Timberlake wanted to keep the partnership going. He was in luck that the producers had cooked up a series of slinky, percussion-driven tracks that would help send Justified to triple-platinum sales — most of which had been written to get the attention of bigger artists like Prince and Michael Jackson. But when those acts weren’t interested, they became Timberlake’s, helping to boost his R&B and hip-hop credentials after years of teeny-bop singles. 

But the cornerstone of Justified was never Neptunes-produced hits like “Rock Your Body,” “Señorita” and “Like I Love You,” which was the album’s first single. They’re all fantastic, but none of them was “Cry Me a River,” which was released after “Like I Love You.” The lead single showed off the Timberlake that people knew — the pop-minded dance artist — but “Cry Me a River” was a little darker, a little more mature. Opening with the sound of pouring rain and what sounded like Gregorian chants, this had a cinematic feel — like you had just walked onto a crime scene in a noir. 

It was the brainchild of a man named Timbaland. 

Around the time that Timberlake was getting involved in NSYNC, the man born Timothy Zachary Mosley was crafting beats for R&B artists like Ginuwine and Aaliyah. (Ginuwine’s anthem “Pony,” which was featured prominently in Magic Mike? That was Timbaland.) But Timbaland’s most fruitful collaboration was with Missy Elliott, the two hooking up for her influential 1997 debut Supa Dupa Fly. Early in the NSYNC days, Timberlake heard the record and made a vow to his mom, Lynn Harless, who was also his manager: “I will work with that man one day … if it’s the last thing I do.” Years later, Timberlake approached Timbaland for Justified, asking him to come up with something that had the same intensity as his Missy material. And so, Timbaland started beatboxing the core rhythm that would become “Cry Me a River.”

This was during a period in which Timberlake was apparently still pretty hung up on Spears, even though they’d split up. In a 2003 interview with Rolling Stone, he referred to someone who had broken his heart, although he wouldn’t say the person’s name. But he wasn’t fooling anyone. “When we were together it was bliss,” he said, “like something from a damn fairy tale. But right now, I just don’t see — it’s just so hard. So hard. I’m the type of person, if I’m not exactly sure about something, then I’ll wait it out and see. I may not ever get over her. That’s why I’m kind of chilling. I’m waiting to see. I do have to come to the realization that I might never.”

That anger and disillusionment came out in the lyrics for “Cry Me a River,” flowing from him effortlessly. In his 2018 book Hindsight: & All the Things I Can’t See in Front of Me, Timberlake recalls his mindset. “I’ve been scorned. I’ve been pissed off,” he writes. “I wrote ‘Cry Me a River’ in two hours. I didn’t plan on writing it.”

You were my sun
You were my earth
But you didn’t know all the ways I loved you
So you took a chance
And made other plans
But I bet you didn’t think that they would come crashing down

As with classics like “I Heard It Through the Grapevine,” the mood was a mixture of rage and sorrow over being jilted — in both songs, the narrator’s discovery that she’s been with someone else sets the whole thing in motion — and the tense backing arrangement suggested the grandeur of Timberlake’s sense of betrayal. “The feelings I had were so strong that I had to write it, and I translated my feelings into a form where people could listen and, hopefully, relate to it,” he writes in Hindsight. “People heard me, and they understood it because we’ve all been there.”

What especially made “Cry Me a River” resonate was how it tapped into the emotional trajectory that many of us — whether we want to admit it — go through when we’re hurt after a breakup. It starts off as wounded and mournful, but as the song reaches its chorus, there’s a sudden vindictiveness to his laments: You’re gonna regret this. But for Timberlake, there seemed to be something else going on as well. Even though his voice was as silky-smooth as always, there was an adult seething to it that suggested a man who was no longer a pin-up. He wasn’t just saying farewell to Spears — he was shedding the boyishness that had defined his early career. 

You told me you loved 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
Cry me a river
Cry me a river
Cry me a river
Cry me a river

What made the song such a standout? Nobody has explained it better than Timberlake himself, who near the end of last year did an Apple Music Essentials in which he looked back at his most famous songs. “It’s a ballad that exists as a tempo record,” he said, “which is very rare.” Not unlike Missy’s breakthrough smash “The Rain (Supa Dupa Fly),” “Cry Me a River” had the swagger of a banger, but its tone was melancholy. There was energy within the slowed-down beat, as if you could feel the swirl of conflicted emotions pulsating through the track. It’s the way that a lot of people are when they’ve been dumped — you’re furious and bereft at the same time, all the while convinced that your despondency is like nothing anyone has ever experienced before. “Cry Me a River” was that epic.

Released to radio in late 2002, “Cry Me a River” went to No. 3, ending up as Justified’s highest-charting single. As striking as the song was, though, the video was even more startling, telling the story of a young man (Timberlake) breaking into his ex’s place once she heads off with another guy. To get his revenge, Timberlake films himself getting it on with another woman in her bed — and then waits for his ex to get back so he can sneak around behind her, watching her shower and then leaving before she realizes that he’s left the video playing on her television. Oh, and the actress who played the former flame, Lauren Hastings, looked just like Spears, so everyone assumed that’s who the song was being addressed to. 

By 2021 standards, it’s indisputable that Timberlake is straight-up stalking his ex in the “Cry Me a River” video, exhibiting the sort of predatory behavior that, in real life, ought to get you arrested. But it’s funny how it didn’t feel that way back then: The clip played like an audacious piece of autobiography, with Timberlake symbolically getting vengeance on the very public figure who had done him wrong. It made him seem edgy and definitely not like a guy who’d been in a boy band.

“One of the things I really liked is it doesn’t paint Justin in the best light, you know?” said Francis Lawrence, the director of the video, in 2017. This was before Lawrence had made the leap to movies, directing blockbusters like I Am Legend and three of the Hunger Games movies. He had pitched the storyline of this video to other artists, including Faith Hill, but it was Timberlake who latched onto its revenge narrative. “He’s stalking around in the rain, wearing a hood to cover himself up, breaking into someone’s house — I mean, it’s all very violating and creepy,” Lawrence said. “He’s getting revenge and he’s obviously not in a healthy sort of place, but I didn’t want to see a sentimental take on the song — I was much more interested in seeing the dark, twisted version, and luckily he went for it. And clearly that scared other people away, but not Justin.”

It fit a moment in Timberlake’s life when he was trying very hard to prove what a bad boy he was. When he was questioned by a radio host if he and Spears had ever had “oral intercourse,” the singer said, “I did it, I’m dirty.” Partly, it was an attempt to ruin her good-girl image, and partly it was the kind of thing a young dude brags about because, at that point in your life, everything regarding sex feels naughty and grownup. But when Rolling Stone questioned him in that 2003 profile about making a video that so obviously had a Britney lookalike as the villain, he tried to insist that it was all a coincidence. 

“I didn’t make this video so I could sit around and talk about it,” he responded. “It’s a video, and when you watch it, either you have a sense of humor or you don’t. [The girl] doesn’t represent anybody. She represents a female in the story line. I haven’t gone public about my relationship.” And yet, in that same interview, he admitted that he had reached out to Spears about the video “because when people blew it way out of proportion, I didn’t want things to get misunderstood. She was cool. We’re cool. I haven’t spoken to her directly about it, because that’s my career, and I don’t speak with people in my personal life about my career, but I can tell you that we are cool. There’s no hard feelings. What is all the fuss about? If anybody is the bad guy in the video, it’s me.”

This probably sounds preposterous now but, believe me, back then “Cry Me a River” was part of a very passionate and public Justin-versus-Britney battle in which fans had to pick a side. I was also dealing with a breakup at that time, so I’m pretty sure I was Team Timberlake, but in hindsight it’s galling how hypocritical the whole situation was. The “Cry Me a River” song painted a picture in which the ex was unfaithful, apparently thereby entitling the singer to behave so petulantly. And in the culture’s mind, Spears was the one pretending to be so wholesome — how could she be so high and mighty and then be so mean to poor Justin? 

Timberlake managed to have it both ways, playing the wronged party and also the predator, getting his vengeance through a hit single and provocative, stylish video. (Years later, he was still casting himself as the victim: “When we initially parted ways I felt like she had a couple of opportunities to just sort of stick up for me, and she didn’t. Which is fine. But at that time, you know, I fought back. … I came up with a song.”) The success of “Cry Me a River” practically validated his stance. He had bested his ex and remade himself as a cocksure solo artist in the process.

You could argue that, by now, “Cry Me a River” is so well-known that the initial shock has worn off. It’s just another song — something that plays in the background, unnoticed. But it can still jolt you when you least expect it. For her 2017 film Lady Bird, a smart but sunny teen comedy, writer-director Greta Gerwig incorporated the ballad during a moment in which her precocious main character goes to a party where she’s going to talk to the cool boy she’s in love with. Gerwig wrote Timberlake a letter asking permission to use “Cry Me a River,” telling him, “I mean, what can I say? You’re Justin Timberlake. You were the soundtrack to my adolescence. Your rise corresponded exactly with my very awkward puberty.” Comparing “Cry Me a River” to “Gimme Shelter” — the Rolling Stones’ apocalyptic late-1960s anthem — she called his song “sultry and sullen and infectious.” There were probably a lot of quirky, self-conscious teens like Gerwig who grew up relating to “Cry Me a River” — they instinctively understood the tangled, thorny desire swirling around in it. 

Both Timberlake and Spears have moved on with their lives, but in some ways our society hasn’t. A forthcoming documentary, Framing Britney Spears, is said to chronicle her struggles with fame, as well as the people who have behaved badly in her life, including Timberlake. One wonders what would have happened if she’d ended up officially releasing a 2004 track, entitled “Mona Lisa,” that seemed to discuss how the media was treating her post-Timberlake. Even so, recently Spears herself has called attention to their past. Last year, she posted on Instagram about his song “Filthy,” writing, “I know we had one of the world’s biggest breakups 20 years ago …… but hey the man is a genius!!!!” She did it again this week, shouting out his song “Holy Grail.” And while the public was probably more on Timberlake’s side back then, lately there’s been a valuable reconsideration — not surprisingly, led by female writers who have pointed out all the ways that he was actually “a trash ex” to Spears.

As for Timberlake, he’s had a very successful post-NSYNC career, but the way he responded to the Spears breakup was repeated soon after during the whole “Nipplegate” Super Bowl controversy. You may recall that he was the one who ripped off Janet Jackson’s breast shield during the performance, exposing her for about a second. And yet, she was the one who got smeared in the press for somehow being too sexual — if anything, she was just a helpless bystander. Timberlake played the victim there, too — his career continued unabated, while hers floundered. And on his second solo album, 2006’s FutureSex/LoveSounds, he recorded another spiteful putdown, “What Goes Around… Comes Around,” that everybody again assumed must be about Spears. That song was an even bigger hit, going to No. 1. 

Justin Timberlake turns 40 today. He’s a global powerhouse who’s also an in-demand actor, and he can be quite good on screen. (He’s a terrific heel in The Social Network.) This week, he’s the star of Palmer, a drama in which he plays a criminal just released from prison who becomes the unlikely guardian of a sensitive neighbor kid (Ryder Allen). Taking on weighty movie roles, Timberlake is yet again wanting us to know he’s a grownup — that he’s not the same adorable teen from NSYNC, or even the glitzy pop superstar who’s dominated the charts for a couple decades. His entire often remarkable career has been built as a means to make us take him seriously. 

“Cry Me a River” was the first salvo in that offensive. He wanted us to know that he was over Britney and that he was over Star Search and The All-New Mickey Mouse Club and NSYNC. The song remains haunting, capturing that sense of heartbreak so palpably — that unfiltered rage we’ve all experienced when the pain is still raw. But breakup songs that are that terrific end up being something of a self-own. The guy singing wants his ex to hurt as much as he does — but the song’s anguish is so deep it’s clear there’s no way that she ever could. The reason why we haven’t moved on from Justin and Britney is that “Cry Me a River” is too good to forget. Justin Timberlake wrote it to get over her, but every time I’ve heard it for the last 20 years, I just think about what a number she must have done on him.