The year is 2002. Justin Timberlake is trying to break away from *NSYNC and prove himself as a solo star. Lucky for him, he has a superstar girlfriend named Britney Spears.

Their fairy-tale relationship wasn’t interesting enough to sell records.

He needed angst. Hardship. Something to justify why a boy as perfect as him could struggle like the millions of fans he was selling music to. After being unfaithful to the girl who loved him dearly for years, she finally had enough and slipped up once. He used that mistake as ammunition and executed a master plan to manipulate a story for his first major hit: “Cry Me a River.”

His plan worked. Justin sold millions of records solo. For two decades, the world thought he was the innocent victim of Britney’s evil ways.

Now Britney has finally told her side. It’s somehow even darker than we imagined.

Justin and Britney’s history goes back to 1992, when eleven-year-olds met on the set of Disney’s “The All-New Mickey Mouse Club.” In her 2023 memoir “The Woman in Me,” Britney recalls: “Once we had a sleepover. We played Truth or Dare, and someone dared Justin to kiss me.” Justin recalled in a 2006 interview: “I was infatuated with her from the moment I saw her.”

They maintained distant friendship as their careers took off. In 1998, *NSYNC was exploding after their debut album sold 4.4 million copies. Britney’s name was circulating as a promising singer, so *NSYNC’s manager invited her to open for the boy band’s tour. They hit major cities across North America, selling out 3,000 to 5,000 capacity venues.

During that tour, Britney released “Baby One More Time.” It hit number one on the Billboard Hot 100. The same week, her debut album hit number one on the Billboard 200—making her the first female artist in history to have a number one song and number one album simultaneously.

Two of the biggest pop sensations on one tour together, friends since childhood. Naturally, rumors of dating began.

“I’ve heard a rumor that you and Justin from *NSYNC have gone out,” an interviewer asked.

“No, it’s not true,” Britney lied.

“Who’s dating Britney Spears? It’s rumored,” another asked Justin.

“I have to say I’m dating Tyra Banks,” he joked.

They were both lying. They kept their relationship secret for as long as possible. It wasn’t until January 2001—over two years later—that they officially confirmed they’d been together the whole time.

By 2001, they were a certified Hollywood power couple. Britney had just released “Oops!… I Did It Again” and already generated 30 million album sales in two years. *NSYNC released “It’s Gonna Be Me” and “Bye Bye Bye” off “No Strings Attached,” which went diamond in the first year.

They performed at Super Bowl XXXV together. Britney did her iconic “I’m a Slave 4 U” performance at the 2001 VMAs, where she claimed Justin helped calm her down before she hit the stage. “I mean, I was in a cage with a live tiger,” she said. “Justin saw I could hardly talk, so he held my hand and gave me a five-minute pep talk. Which obviously worked.”

The media adored them. Pet names at a charity basketball game: “Pinky and Stinky.” Their jersey numbers: one and two. Five to make two together.

She told The Guardian in 2001 that Justin was living at her house in Los Angeles during his downtime. “I’m not ashamed at all to say that I love him from the bottom of my heart,” she said. “As far as love is concerned with him, too much is not enough. He’s everything. We’ve gone through so much together. We know each other inside and out.”

While filming her 2002 movie “Crossroads,” the director said Justin was regularly on set supporting her. The director had Britney absentmindedly doodle in a notebook in character. “I have the book,” the director said. “All she was writing was Britney and Justin. All these little curly cues. It was like looking at a teenage girl’s musings. Hearts and butterflies in Justin’s name.”

Fans still look back at old footage and see how deeply in love Britney was.

“I think everybody who listens to it will be totally surprised,” Justin said of her music. “I think it’s the best her voice has ever sounded.”

“Thanks,” she said softly.

There is nothing stronger than a first love. Britney was twenty years old, extremely vulnerable, greatly attached to her childhood lover. Which is why the world was shocked when, in March 2002, she announced their breakup.

“Can I ask you, are you single at the moment?” an interviewer asked.

“You really don’t want to talk about anything at all? You can just hide.”

“I want to say I’m single right now,” Britney said.

The tabloids ran wild throughout 2002, speculating why the perfect couple separated. Justin remained quiet. Instead, he released his first solo single, “Like I Love You,” in early September 2002.

A shock to the pop world. *NSYNC just had a smash hit with “Girlfriend” all summer. Typically, when a band member releases solo material, speculation of a breakup follows. Speaking of breakup—the exact same week Justin released his song, tabloids began spreading the narrative that Britney had betrayed Justin. That cheating drove them apart.

As if the narrative couldn’t favor Justin more, he was labeled “sexy and single” by the media.

“Like I Love You” debuted at number 67 on the Billboard Hot 100—lackluster for the lead singer of the biggest pop group in the world. Conveniently, a couple weeks later, new exclusive never-before-seen pictures of Britney and Justin were leaked to tabloids.

I wonder who had those never-before-seen pictures.

With the boost in media attention, his song climbed the charts, peaking at number eleven in October. Once it started losing steam, he finally spoke publicly about the breakup—with Barbara Walters.

“We sat down,” Justin said, “and I said to her, if there’s ever a moment where you ever need me, you can rest assured that I will be there because I love you as a person. I promised her I wouldn’t say specifically why we broke up.”

He did the interview alongside his mom, which made him look like a sweet, innocent mama’s boy who got his heartbroken.

“I cried with him,” his mom said. “I just want him to be happy. He was heartbroken.”

“Put your head on Mommy’s shoulder,” Barbara said.

“It was tough for us,” Justin added.

Many songs on “Justified” were about heartbreak, betrayal, and relationships. Justin said they weren’t about Britney. Yet when a reporter sat him at a piano and asked him to play something from the album, he chose instead to play a song nobody had ever heard.

The lyrics: “Thought I loved was so strong. I guess I was dead wrong. But to look at it positively—hey girl, at least you gave me another song about a horrible woman.”

That last line. “At least you gave me another song about a horrible woman.” Blatantly obvious it was about Britney. It also stamped that his next song, “Cry Me a River,” was about this “horrible woman.”

Justin allegedly called Britney to let her know a woman would be acting as her doppelgänger in the music video. She was still shocked to realize the video basically recreated and dramatized their breakup.

“You don’t have to say what you did, I already know. I found out from him. Now there’s just no chance with you and me. Cry me a river.”

After the song and video dropped, the media frenzy established a war between Britney and Justin. He continued doing press. Nearly every interview asked about her.

“Is it frustrating to promote an album when all anyone wants to talk about is Britney?”

“So anyway, Britney—can I just mention Britney for a minute?”

“Sure.”

“You did go out with Britney Spears. That ‘Cry Me a River’ video—who’s that about?”

“Cry Me a River” peaked at number three on the Billboard Hot 100. It proved Justin could stand alone without *NSYNC. Timbaland, who produced the track, recalled the moment: “I think the aha moment for me was when I was in the studio beat boxing. He walked into the room, had his face down, then started humming. I’m like, oh, this is the one.”

His debut album sold 439,000 copies first week, landing at number two on the Hot 200. The album went triple platinum.

His plan worked.

Britney gave Justin much more grace. She didn’t entertain the tabloids. She hardly gave interviews. She didn’t try to rewrite the narrative. Many believe her 2003 VMAs stunt—kissing Madonna on stage—was a way to get back at him. At least that’s what the media pushed, zooming in on his face.

“That kiss thing? I was disgusted as you were,” he said. “No, I wasn’t disgusted. I was just not impressed. I expected a lot more. It’s the VMAs, you know.”

Britney finally spoke about the breakup over a year and a half later. Diane Sawyer seemed to interrogate her.

“He’s gone on television and pretty much said you broke his heart. You did something that caused him so much pain. What did you do?”

“I was upset for a while,” Britney said. “We were both really young. I will always love him. He’ll always have a special place in my heart.”

“But you said you’ve only slept with one person in your whole life, two years into your relationship with Justin. Yet he’s left the impression that you weren’t faithful. That you betrayed the relationship.”

“I think everyone has a side of their story,” she said carefully. “I’m not technically saying he’s wrong. But I’m not technically saying he’s right either.”

Meanwhile, Justin did interviews bragging about sleeping with her.

“Justin Timberlake is in the house! I just want to ask you one question: did you—Britney Spears? Yes or no?”

“Oh man. Come on, man. Okay, I did it.”

He later admitted it was weird. “There was talk about what we did together, sexually and stuff. I felt very exploitative and very weird.”

Despite everything, Britney chose not to bash him. When asked about the “Cry Me a River” video:

“I saw it on vacation. Someone called and told me it was going to come on. I watched it. I was kind of in denial. But it’s fine. That’s the way he had to deal with what happened. I know if I was in a relationship and something happened, I couldn’t really go there. But it’s out there. Let’s talk about something else.”

At the time, Justin’s fans thought she wasn’t speaking ill of him because she was actually wrong—she did cheat, she accepted the narrative because it was true.

But Britney fans always suspected something was weird. Their breakup didn’t make sense. She loved him. Why would she cheat? There had to be missing information. Plus, his successful solo launch after departing the biggest boy band in the world, the media heavily favoring him—it felt too convenient.

Like it was all part of a plan.

Especially after his second controversy one year later. The 2004 Super Bowl halftime show. Justin was the one who ripped Janet Jackson’s breast covering off. Janet was banned from radio, crucified by the media. Justin remained silent. Didn’t come to her defense. Skated by totally unscathed.

Justin Timberlake advanced his career by benefiting from two major controversies while looking like the innocent sweet boy.

Now, twenty years later, Britney finally spoke in her memoir “The Woman in Me.” Key details she hid for two decades shine a much-needed light.

“There were a couple times during our relationship when I knew Justin had cheated on me,” she wrote. “Because I was so infatuated and in love, I let it go.”

When *NSYNC went to London in 2000, photographers caught him with a girl from All Saints in a car. She said nothing. Another time in Vegas, one of her dancers told her Justin gestured toward a girl and said, “Yeah man, I hit that last night.” She didn’t name the girl—”she’s actually very popular and she’s married with kids now.”

There were rumors about him with various dancers and groupies. “I let it all go. Clearly he’d slept around. It was one of those things where you know but you just don’t say anything.”

“So I did too. Not a lot. One time with Wade Robson. We went to a Spanish bar. We danced and danced. I made out with him that night.”

She was loyal to Justin for years. Only had eyes for him. With that one exception, which she admitted to him.

Justin never mentioned to the press that he cheated on Britney multiple times during the rollout of “Justified.” That would have devalued his narrative—that he was a broken innocent boy taken advantage of by an evil woman.

But Britney’s story gets even sadder.

“At one point when we were dating, I became pregnant with Justin’s baby,” she wrote. “It was a surprise, but for me it wasn’t a tragedy. I loved Justin so much. I always expected us to have a family together one day. This would just be much earlier than I’d anticipated.”

Justin wasn’t happy. “He said we weren’t ready to have a baby in our lives. That we were way too young.”

She understood. She didn’t want to push him into something he didn’t want. Their relationship was too important to her.

“I agreed not to have the baby. Abortion was something I never could have imagined choosing for myself. But given the circumstances, that is what we did.”

She described the process in detail—physically and emotionally painful. Looking back, fans realize her song “Everytime” was about suffering the loss of her child, comparing it to the magnitude of losing your own life.

Justin was there for her at the time. But little did she know he was planning to break up with her.

“When Justin began making ‘Justified,’ he started being very standoffish with me,” she wrote. “I think that was because he decided to use me as ammunition for his record. It made it awkward for him to be around me staring at him with all that affection and devotion.”

Ultimately, he ended their relationship by text message while she was on set for a video shoot.

She also wrote that Justin’s family was the only loving family she had. She spent all her holidays with them. Now she was broken, alone, and suffering the wrath of a media fueling the false narrative that she was an unfaithful cheater.

“I felt there was no way at the time to tell my side,” she wrote. “I couldn’t explain because I knew no one would take my side since Justin had convinced the world of his version. I don’t think Justin realized the power he had in shaming me. I don’t think he understands to this day.”

In 2021, after the #FreeBritney movement successfully got her out of her thirteen-year-long conservatorship, Justin issued a public apology to Britney Spears and Janet Jackson.

“I specifically want to apologize to Britney Spears and Janet Jackson, both individually,” he wrote. “Because I care for and respect these women, and I know I failed.”

The apology was random. Nobody expected it. Vague. He didn’t go into detail.

Britney released her memoir in 2023. After she detailed the cheating and the abortion, Justin was asked about the apology. His response?

“I’d like to take this opportunity to apologize to absolutely fucking nobody.”

The way the media treated Britney can’t be entirely blamed on Justin. She suffered before and after she dated him. You can’t blame him for her downward spiral or the unjust conservatorship.

But there’s no doubt he saw an opportunity to advance his career at the expense of Britney’s public perception. Maybe he thought it wouldn’t be that bad. Maybe he thought the money she’d make would be worth it. Maybe he just didn’t care about her the same way she did.

Now, over two decades later, Justin is not sorry.

After his recent DWI arrest, the media is diving deep, speculating about his potential addiction. The internet is spreading false information about what was in his system. The narrative is starting to shift against Justin Timberlake.

The tables have turned—a little bit.

But Britney carried that weight alone for twenty years. And Justin? He got a number three hit, a triple platinum album, and a solo career. He got away with it.

Cry him a river? He’s the one who built the damn thing.