Jamie Lynn Spears Reveals Britney Spears' Reaction to Justin Timberlake's 'Cry Me a River'

01/19/2022 12:16 am EST

Jamie Lynn Spears is teasing new behind-the-scenes tidbits about her older sister Britney Spears in her upcoming book Things I Should've Said. In a new interview on the podcast Call Her Daddy, Jamie Lynn recalled her older sister's relationship with singer Justin Timberlake. She even opened up about Britney's reaction to Timberlake's breakup song "Cry Me a River."

Britney and Timberlake dated from 1999 to 2002, and Jamie Lynn said: "That was probably one of the best times in my whole family's life." Though she would have been nine years old when the relationship started, Jamie Lynn said: "Things were good and we were experiencing the good side of things. But I just remember that he was pretty thoughtful... I just felt like he was funny." She even recalled being personally distraught when the couple broke up.

"I don't really know why I was so sad, but I was because I think everybody thought it was forever. But I was so sad first off because my sister was so sad," Jamie Lynn said. "That also too was the first time I saw [that] maybe I didn't know everything about the relationship, because perhaps they were protecting me. Obviously, why would they talk to me about anything? It was really sad, though, seeing my sister be so heartbroken."

Jamie Lynn also lamented her sister's treatment by the press, saying that she and Timberlake were "criminalized" and "held to a different standard" because of their celebrity status. She felt like that pressure compounded when Timberlake's song "Cry Me a River" came out in 2002.

"Looking back with that perspective and seeing how heartbreaking it must've been for my sister when 'Cry Me a River' came out," Jamie Lynn said. "Don't get me wrong, that's a way to launch your solo career, but I felt really sad."
To be fair, Timberlake has never confirmed that "Cry Me a River" was about Britney, so even Jamie Lynn is just speculating here. She seemed confident in speculating that her sister's song "Everytime" was a direct response, as well.

"My sister, she wrote that song 'Everytime,' and she's obviously beyond brilliant when it comes to anything creative and she picked that song out on the piano, and she wrote it, and it still makes me cry because I think about how heartbroken she was," Jamie Lynn said. "That was his song, but 'Everytime' was her song. It still breaks my heart to think about that."

Many of Britney Spears' die-hard fans have condemned Jamie Lynn and mocked her recent spate of interviews in promotion of her memoir. They believe that Britney distrusts her sister along with the rest of her family after her prolonged conservatorship. Jamie Lynn's memoir was released on Tuesday, Jan. 18, and is available now wherever books are sold.

Disclosure: PopCulture. is owned by Paramount. Sign up for Paramount+ by clicking here.