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This article is written by a student writer from the Her Campus at UCF chapter.

Britney Spears’ The Woman In Me memoir has generated controversy about one of the most famous (or infamous) celebrity couples in recent history: Justin Timberlake and Britney Spears’ relationship circa 1999 to 2002. 

The two began dating during the rise of their popularity. Timberlake was still the lead singer of the popular boy band NSYNC and Spears was in the beginnings of what was to become full-fledged pop superstardom. At the beginning of their relationship, everything seemed to be perfect: two young stars in a well-publicized media relationship with their whole careers in front of them. No one predicted that by the time Timberlake’s debut solo album Justified was released in November of 2002, they would be well and truly split. 

Spears was thought to be the cause of the relationship’s untimely end due to swirling infidelity rumors. In his single “Cry Me a River” Timberlake alluded heavily to these allegations, depicting an actress with Spears’ likeness and singing of a breakup fraught with cheating and betrayal. This blow to her reputation could not have been more well-timed.

‘Cry Me A River’ Offical Video: Youtube

If Spears wasn’t targeted before, this single solidified the media’s opinion: Spears was slut-shamed and reviled as the woman who broke Timberlake’s heart. The song brought opinions of Spears crashing down while catapulting Timberlake to solo success. 

It wasn’t until the release of the Framing Britney Spears documentary in 2021 that a new perspective on the situation  — and Timberlake himself — was provided. The ‘Free Britney’ movement, although active after the conservatorship was placed in 2008, gained traction in 2019 and the documentary only solidified the anger and support of the public in her favor. In February of 2021, only a week after the documentary’s release, Timberlake publicly apologized for contributing to Spears’ character assassination in the 2000s and for a disrespectful Super Bowl incident involving Janet Jackson. 

Timberlake’s role in Spears’ infamous fall from grace allowed for examination from a new lens. As a male singer who solidified a reputation as a “good guy” in the media, his actions allowed the public to read between the lines to see how he contributed to and profited from Spears’ public shaming. 

In Feb. 2024, all of this controversy was stirred up yet again by the release of Britney Spears’ memoir The Woman In Me, which caused unknown details about their relationship to surface. 

After Spears apologized for any harm her book may have caused individuals discussed in the memoir, Timberlake took to the stage at one of his concerts to make it clear he felt no such sentiments before segueing into “Cry Me a River.” Timberlake’s lack of guilt over his actions during their relationship has shed light on his true feelings about their complicated past. 

Has Timberlake owned enough of his actions, or is there blame to be cast and a deeper conversation to be had? Read The Woman In Me (available as a free audiobook with Spotify Premium) and decide for yourself.

Hadley is a sophomore at the University of Central Florida majoring in Writing and Rhetoric, with a minor in Creative Writing. They love collecting records, thrifting, writing about music, and re-watching NBC Hannibal. You can probably find them sipping a lavender latte, daydreaming about next year's Spotify Wrapped, and pretending they live in the 70s.