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Background and development
Oops!... I Did It Again would become Spears' second studio album, following her debut ...Baby One More Time, which was released on January 12, 1999. When asked about in what her second album would differ from her debut, the singer stated, "when I did the first album, I had just turned 16. I mean, when I look at the album cover, I'm like, 'Oh, my lordy'. I know this next album's going to be totally different--especially the material." Spears recorded the first songs for the album in Sweden in late 1999. "I just got finished recording the first six songs in Sweden two months ago, and the material is so much more funkier and edgier. And, of course, it's more mature because I've grown as a person too." In an interview with MTV, the singer revealed that she was satisfied with the recorded material, but the time to work on new tracks was really limited, "so I've just really been in the studio nonstop, which is cool, though." Spears also addmited that there was pressure of making a good follow-up to ...Baby One More Time, because the debut album had sold over ten million units in the United States alone, and over 30 million worldwide. "It's kind of hard following ten million, I have to say. But after listening to the new material and recording it, I'm really confident with it."

At the time, the singer had already collaborated with many songwriters and producers, such as Max Martin and Eric Foster White, who did most of her debut album, besides Diane Warren and Kenneth Brian "Babyface" Edmonds. She also traveled to Switzerland, where she worked with producer Robert Lange on a track titled "Don't Let Me Be the Last to Know", co-written by Country singer-songwriter Shania Twain. After finishing the track, Spears revealed in an interview with Billboard that "with the first album, I didn't get to show my voice off. The songs were great, but they weren't very challenging. This song is incredible. It's going to surprise people in the best way." Back to the United States, she recorded more songs for the album. After the 42nd Grammy Awards, on February 24, 2000, Spears went to Pacifique Recording Studios in Hollywood with producer Rodney "Darkchild" Jerkins on a cover of "(I Can't Get No) Satisfaction", originally recorded by The Rolling Stones in 1965. Spears also wrote her own autobiographical song for the album, titled "Dear Diary". Kristian Lundin also worked with her on tracks for Oops!... I Did It Again; however, they didn't make into the final track listing. The album was released on May 16, 2000 through Jive Records.

Composition
Spears had originally envisioned an album "more mature sounding ... [with] a little more of a hip-hop flair." The first song is the title track, "Oops!... I Did It Again", a teen pop and dance-pop song that lasts for three minutes and thirty-two seconds. The theme of the song evolves around an alleged relationship where a man is attracted to a woman. The woman, however, says that she "not that innocent", and is only playing with the man's feelings. The next song and third single, "Stronger", was noticed by music critics as Spears' declaration of independence, which is perceived in self-empowerment lines such as "I'm not your property" and "I don't need nobody". Despite not being written by the singer, it was speculated that the song is directed to the singer's record label and her management. "Stronger" is then followed by "Don't Go Knocking on My Door". David Browne of Entertainment Weekly noted that both tracks are reminiscent of The Rolling Stones' "The Last Time" (1965). The fourth track is the cover of "(I Can't Get No) Satisfaction", which was deemed by Stephen Thomas Erlewine of Allmusic a "clenched-funk revision" of the original version. "Don't Let Me Be the Last to Know" is a teen pop ballad which, according to Stephanie McGrath of Jam!, is "a nice break from the 'baby babys', 'yeah yeahs' and insistent drum beats that pepper the other songs" of Oops! [sic].

The seventh track and second single, "Lucky", has a rhythm similar to the ones of Spears' previous singles "...Baby One More Time" (1998) and "Sometimes" (1999). Lyrically, Spears tells "a story about a girl named Lucky," who is a famous pop star that, despite having all that she wants, still feels lonely inside. "One Kiss From You" is a mid-tempo love song in which the singer declares, "You give me strength/ You give me hope/And when you hold me in your arms you make me whole," while on "When Your Eyes Say It", written by Diane Warren, she "looks deep into her lover's eyes to discover the true depth of his affections." In "Where Are You Now", Spears displays her vocal range by belting during the final chorus in "Mariah- and Celine-style". The closing track is "Dear Diary", an autobiographical song in which the singer reflectes "about a girl who is interested in this guy, and she comes home every night and writes about it."

Controversy
In 2002, Spears and her recording and publishing companies have been sued by two musicians claiming two of her songs were copied from their tune. Michael Cottril and Lawrence Wnukowski filed a copyright case against Spears, Zomba Recording Corp, Jive Records, Wright Entertainment Group and BMG Music Publishing. Cottrill and Wnukowski claim that "What U See (Is What U Get)" and "Can't Make You Love Me" are "virtually identical" to one of their songs, which was copyrighted in 1999. They say this song was submitted to one of Spears' representatives for consideration on a future album, but it was eventually rejeceted. "More than anything, we want the recognition that we wrote a good tune. We were hoping this was 'the' hit for us, a really well-done tune."

Critical reception
Oops!... I Did It Again received positive reviews from most music critics. The album holds a score of 72 out of 100 (indicating "generally positive reviews") based on 12 critical reviews, according to the music review aggregator Metacritic. Stephen Thomas Erlewine, senior editor of Allmusic, said the album "has the same combination of sweetly sentimental ballads and endearingly gaudy dance-pop that made One More Time," but added that, this time, "fortunately, she and her production team not only have a stronger overall set of songs," but they also "occasionally get carried away with the same bewildering magpie aesthetic that made the first album's "Sodapop" -- a combination of bubblegum, urban soul, and raga -- a gonzo teen pop classic." A NME staff reviewer gave the album an 8 out of 10, and stated, "the reason why Britney Spears has sold 28 million albums across the globe is because she's modern-day pop perfection realised in a, nearly, human form. Like it or not, the songs penned for Britney by Swedish producer Max Martin, the man behind the even more successful Backstreet Boys, get into your brain like ketamine. An all-encompassing, horrendously realised high - once it's inside you, there's little you can do to stop it, you must give in. In its own sick way, Britney is drug music."

Stephanie McGrath of Jam! thought that Oops!... I Did It Again "is not a work of art or a shocking departure" from Spears' debut album, but concluded that it is a good pop album "that will satisfy Spears' fans until the third one which, she promises in her autobiography, will be 'definitely more of a stretch for me creatively'." Rob Sheffield of Rolling Stone commented that the great thing about the album is that "under the cheese surface, Britney's demand for satisfaction is complex, fierce and downright scary, making her a true child of rock & roll tradition." Entertainment Weekly contributor David Browne thought that the producers and songwriters tried to replace the "Tinkertoy feel of Spears' first album and replace it with palpitating, bass-heavy constructs; you'll feel as if you've been whisked away to some steely futuristic gotham." Browne then went to compare Spears' vocal abilities with the ones of fellow recording artist Christina Aguilera, saying that "Spears' artificial-sweetener voice is much less interesting than the settings, yet that blandness is actually a relief compared with Aguilera's numbing vocal gymnastics" At its finest, Oops! reminds us once again that the best new pop can be a blast of cool air in a stifling room." Calgary Sun newswriter David Veitch stated that the album "marks no drastic change in musical direction, although many of the lyrics come from a post-fame perspective," while Tom Terrell of MTV admitted that it "proves beyond a doubt" that Spears is a true artist.

Chart performance
During its first day of release in the United States, Oops!... I Did It Again had sold over 500,000 units. According to Billboard, industry sources suggested that the album would sell over 1 million units, enough to make it the highest sales in a week by a solo female artist. Such record was previously held by Mariah Carey with her 1995 studio album Daydream, with a total of 760,000 units. By the end of the week, Oops!... I Did It Again debuted at number one on the Billboard 200, with over 1.3 million units sold. With only three months of release, the album had already sold almost 5 million units in the country alone. As of July 2012, the album has sold over 10 million units in the United States, making it Spears' second best selling album after ...Baby One More Time.