The singer's sophomore LP dropped on May 16, 2000 -- and Spears celebrated the memorable day with a special post on May 16, 2020. Sharing a compilation video on Instagram, the pop star shared a memory from when she released it and thanked her fans for "sticking with me." "Thank you to whoever made this ….. I just nearly dropped my phone I wasn’t expecting it ??? !!!!! 20 years since the Oops! ? album," she wrote. "The anticipation and the butterflies I felt before it came out were crazy …. all of my expectations were exceeded !!!! And it’s all thanks to you folks …. thank you for sticking with me and growing with me. I am one Lucky girl ⭐️?PS you see even 20 years ago I still liked to twirl ???✨ !!!!"
Around the same time, Brit Brit was still battling for autonomy over her finances. The 38-year-old singer has been under a conservatorship since 2008, a legal concept in which a judge appoints a responsible person or organization to act as the legal guardian, making the calls on everything from finances to personal decisions for the conservatee. After Britney's father, Jamie Spears, stepped down as her conservator last September, the singer's longtime care manager, Jodi Montgomery, took over. However, her mother, Lynne, filed a request with the Los Angeles County Court on Monday, hoping to receive special notice on "all matters" in regard to Britney's SJB Revocable Trust. "Britney has always struggled with her mental health so Lynne's concern for Britney is never-ending. She is her mother and hates to see her suffer," a source told ET in July 2020. "Lynne filed for transparency to keep an eye on the finances because she knows Britney has her ups and downs. She has been doing much better; she is in regular therapy and exercising. Lynne sees a huge improvement."
The Mickey Mouse Club, alongside future stars like Christina Aguilera, Ryan Gosling, and future boyfriend Justin Timberlake.