The album went on to sell over 20 million copies and be diamond certified by the Recording Industry Association of America.
And the 38-year-old pop star marked the two decades since her sophomore album's release with a sweet message to her fans for growing with her for over 20 years.
She shared a video created by a fan showing clips of her from 2000 ahead of the album's release and said 'thank you to whoever made this.'
'I just nearly dropped my phone I wasn't expecting it,' she wrote alongside laughing emojis. '20 years since the Oops! album.
Explaining how she felt at the time, she added '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,' she wrote with a wink seemingly referencing her second hit single from the album, Lucky.
'God Bless and thank you all! PS you see even 20 years ago I still liked to twirl.'
In the video, the then 18-year-old Britney gushed over her lead single and song the album would be named after.
'Actually I just got finished hearing the first single,' she said at the time. 'And I'm so happy about it. It's incredible, it's amazing and I think it's better than Baby One More Time.'
'It's really really weird that my name is known all around the world...It's really exciting.'
She explained that the album would be 'more mature' than her last.
While the album sold millions of copies around the world and became Britney's second best selling album, the hit single may be the most iconic.
Her latex red outfit from the Oops music video, has become synonymous with this era of her career.
But the video's stylist recently revealed that the outfit almost never happened, while speaking to Vogue.
'We wanted everything to be sexy and monochromatic,' Estee Stanley said of Britney's vision for the video.
With the help of costume designer Michael Bush they worked closely to create the iconic outfit.
'It was a last-minute thing to go to him and see if he could make something for us,' said. 'In [the music] world, everybody has to do everything in two minutes, so we knew he could pull it off. And he did.'
According to Stanley the red latex catsuit was made overnight for the video shoot and since latex is not a forgiving fabric, Britney has to pull through in the look.
'If you put a latex outfit on, you're immediately sweating, and I knew she was going to be dancing all day. I was nervous that she would pass out,' Stanley explained. 'After one take, I unzipped her, and it literally looked like a bucket of water poured out of this jumpsuit. She had a very intense day, to say the least.'
Britney went on to release seven more albums after Oops, with her latest being Glory in 2016.
Known as the Princess of Pop, her work inspired other pop stars including Katy Perry and Meghan Trainor, she was honored wit the Billboard Millennium Award in 2016.
