Together, Britney Spears and Justin Timberlake were one of the biggest celebrity couples of all time. That doesn’t mean that the relationship between Spears and the “SexyBack” singer was always easy. Spears revealed that Timberlake dumped her while she was in the middle of shooting one of her iconic music videos. The “…Baby One More Time” star said the incident impacted her for months.

Britney Spears said Justin Timberlake used her as ‘ammunition’

In her 2023 memoir The Woman in Me, Spears gave fans more insight into her relationship with Timberlake than ever before. “When Justin began making his first solo album, Justified, he started being very standoffish with me,” the “Womanizer” singer recalled. “I think that was because he’d decided to use me as ammunition for his record, and so it made it awkward for him to be around me staring at him with all that affection and devotion. “For context, Justified is mostly remembered for “Cry Me a River,” which was widely viewed as a diss track directed at Spears.

“Ultimately, he ended our relationship by text message while I was on the set for the video for the ‘Overprotected’ remix by Darkchild,” she added. “After seeing the message as I sat in my trailer between takes, I had to go back out and dance.” While Spears was shooting the music video for an empowering song, she was actually in a dark place emotionally.

Justin Timberlake devastated his ex-girlfriend

Spears explained why Timberlake’s actions weighed on her so much. “For as much as Justin hurt me, there was a huge foundation of love, and when he left me I was devastated,” she wrote. “When I say devastated, I mean I could barely speak for months. Whenever anyone asked me about him, all I could do was cry. I don’t know if I was clinically in shock, but it felt that way.”

The messy relationship between Spears and Timberlake impacted both of their subsequent music. Spears wrote a yearning ballad about Timberlake called “Everytime.” In addition, Timberlake released an angry ballad called “What Goes Around…/…Comes Around” that was interpreted as a being about Spears.

Britney Spears’ ‘Overprotected’ didn’t pan out

“Overprotected” was a big part of Spears’ personal life, but it wasn’t much of a hit. The tune merely reached No. 86 on the Billboard Hot 100, staying on the chart for five weeks. Considering the tune was by one of the biggest celebrities on earth, it must’ve felt like a disappointment at best.

“Overprotected” appeared on the album Britney. That record climbed to No. 1 on the Billboard 200, staying on the chart for 58 weeks in total. It spent more time on the Billboard 200 than any of Spears’ other albums besides her first two: …Baby One More Time and Oops!… I Did It Again.

Britney produced one other hit: “I’m a Slave 4 U.” That tune reached No. 27 on the Billboard Hot 100 and spent 14 weeks on the chart. While “I’m a Slave 4 U” has a catchy beat and some sultry lyrics, it might be more remembered for its music video than anything else.

“Overprotected” is one of Spears’ most underrated songs and the story behind it is compelling as well.