On May 16, 2000, Britney Spears released in the United States her second studio album, Oops!... I Did It Again. The album had already been released in Japan on May 03, and Austria, Germany and Switzerland on May 15.
Preceded by its lead single of the same name, which came out a month prior, Oops!... I Did It Again debuted at #1 on the Billboard Hot 100, getting the #1 in 20 charts around the world, #2 in six other countries and #5 in Italy. It broke the record for the biggest first-week sales by a female artist ever in the US, with 1, 319, 193 copies sold, a record she held until 2015, when Adele released 25. It reportedly sold over 500,000 copies just during the first day. It still holds the record for biggest first-year sales by a female, with 7.89 million copies sold in 2000, landing at #4 in the year-end chart of that year. It also appeared on the year-end chart again in 2001 at #28. Oops!... I Did It Again was also the #6 most sold album of the 00's. It became her second album to receive the Diamond certification from the RIAA.
Much as its predecessor, Oops!... I Did It Again is a teen pop / dance pop album, though it has more influences of funk and R&B, with an overall more mature and aggressive tone. Whereas ...Baby One More Time was filled by mostly bubbly ballads and heartbreak songs, Oops! has a more adult sound with tracks like Don't Let Me Be the Last to Know or Where Are You Now, and its mid-tempos gravitate towards the empowerment, in tunes like Oops!... I Did It Again, Don't Go Knockin' on My Door, What U See (Is What U Get), or the Rolling Stones cover (I Can't Get No) Satisfaction, with Stronger even nodding at her debut single by revealing her "loneliness ain't killing her no more". However, it doesn't completely leave aside the sweet melodies that characterized her debut album, with songs like One Kiss from You, Dear Diary or the bonus track Heart.
The album was mainly produced by Max Martin and Rami Yacoub, but it counted with the collaborations of Rodney "Darkchild" Jerkins, Jake Schulze, Mutt Lange, Per Magnusson, David Kreuger, Steve Lunt, Larry "Rock" Campbell, Kristian Lundin, Rober Jazayeri, Paul Umbach, Timmy Allen, Barry J. Eastmond and Eric Foster White, the latter of which produced You Got It All, a cover from The Jets, which was originally recorded for her debut album.
Most of the producers also provided the lyrics of the tracks, but additional songwriters include Alexander Kronlund, Mick Jagger and Keith Richards (for the Satisfaction cover), Shania Twain (for Don't Let Me Be the Last to Know), Keith Scott, Jörgen Elofsson, Andreas Carlsson, Diane Warren (When Your Eyes Say It), Jason Blume, Eugene Wilde, Rupert Holmes (You Got It All) and George Teren. Britney herself co-wrote Dear Diary.
The album was recorded in 1999 after her ...Baby One More Time Tour finished, most of the recording taking place in November. The recordings took place between New York, Hollywood, Orlando, Sweden and Switzerland. The first songs to be recorded at the Cheiron Studios in Stockholm were Oops!... I Did It Again, Walk on By, What U See (Is What U Get) and Don't Go Knockin' on My Door, followed by Stronger and Lucky, which along with Oops!, weren't finalized until January. Don't Let Me Be the Last to Know was recorded in December at Robert "Mutt" Lange's villa in Switzerland. Girl in the Mirror and Can't Make You Love Me were recorded in mid-January at Parc Studios in Orlando, Florida. She then recorded When Your Eyes Say It and One Kiss from You in New York, along with Dear Diary and Heart. Finally, in late February she recorded (I Can't Get No) Satisfaction at Pacific Recording Studios in Hollywood, California. You Got It All and Where Are You Now were outtakes from her debut album.
Four singles were released in order to promote the album: Oops!... I Did It Again, Lucky, Stronger and Don't Let Me Be the Last to Know.
She also embarked on a world tour, the Oops!... I Did It Again Tour, that lasted from June 20, 2000 through January 18, 2001.
For the release of the album she held a special presentation in Tokyo and Paris, and she also made several appearances on MTV and other TV shows in the United States.
The day of the release, she appeared on TRL to talk about the record, and she was signing some CD's for her fans.
A week earlier, she recorded the "First Listen" of the album, where they played a preview of each of the tracks.
The album was released on vinyl in 2019, and it got a new cassette release in 2020 for its 20th anniversary.