Spears and Timberlake were a ‘90s power couple, but when they split in 2002, things got messy. Two decades later, Timberlake apologized to Spears for his part in fueling speculation that she cheated on him by writing “Cry Me a River.”
“I am deeply sorry for the times in my life where my actions contributed to the problem, where I spoke out of turn, or did not speak up for what was right,” Timberlake wrote via Instagram in February 2021 after his relationship with Spears was put under a microscope in the Framing Britney Spears documentary. “I understand that I fell short in these moments and in many others and benefited from a system that condones misogyny and racism.”
In addition to her relationship with Timberlake, Spears’ marriages — and divorces — have been highly publicized. Following her split from Kevin Federline in 2007, Spears was placed under a conservatorship in 2008. The legal agreement came to an end in fall 2021.
Scroll down for the singer’s complete dating history: