Retro review: Britney Spears’ Oops!... Did It Again! turns 25
May 26, 2025
May 2025 marks the 25th anniversary of Britney Spears’ second album, which has been re-released to commemorate the occasion. David Ho takes a look back
The year was 2000. Tracksuits and crop tops were the fashion must-haves, e-mails and chatting online felt like a novelty, flip phones were the trend, and catchy teen pop dominated the music charts with a young girl from Louisiana leading the pack.
After Britney Spears emerged with her debut song (and album) …Baby One More Time at the end of the 90s, she dominated public imagination in a way not seen since Madonna’s first imperial phase. With the mammoth success of her debut, the pressure was on for the teen entertainer to deliver a worthy follow-up and prove that she wasn’t just a flash in the pan.
Fortunately, Spears delivered. The release of the Oops!... I Did It Again! album broke several records, including making her the female artist with the highest first-week sales ever, a title that she held until Adele released 25 in 2015.
If its title hasn’t given it away, the goal of replicating her success is what informs the creation of Oops!.... The formula is followed down to a tee, from Max Martin-led productions down to the inclusion of a groovy oldies cover (previously Cher’s “The Beat Goes On” on …Baby and this time, the Rolling Stone’s "(I Can't Get No) Satisfaction") on the standard track listing.
…Baby was a largely saccharine affair, despite the controversy behind Spears’ schoolgirl look and the purported double entendre of its title track. Oops!... continues some of the coquettish sugar rush of her debut, most noticeably with its campy first single complete with a dialogue referencing the movie Titanic. The now iconic music video for “Oops!...” sees Spears decked out in a red bodysuit dancing it out on Mars. Interestingly enough, the space concept was originally intended for the “…Baby” video before Spears objected and came up with the schoolgirl concept.
Spears’ version of "(I Can't Get No) Satisfaction" is not particularly memorable as a record. But her live striptease take of the song with a remixed version of “Oops!...” at the 2000 MTV Video Music Awards continued her solid streak of headline generating performances at the event, something that would become as defining of her as it was of the awards.
While “Oops!...” was camp in the best possible way, some of the other bits on the record haven’t held up as well. We have some schmaltzy inclusions from surprising superstar contributions, like the Shania Twain-penned "Don't Let Me Be the Last to Know", Diane Warren’s offering "When Your Eyes Say It", and the album closer “Dear Diary” co-written by Spears herself. Even with a steamy video for "Don't Let Me Be the Last to Know" with French model Brice Durand, which was said to make then beau Justin Timberlake jealous, all the aforementioned songs sound rather dated and of its time by now.
One of the singles that seemed aimed at Spears’ younger fanbase at the time is the second single “Lucky”. A teen bop ballad about a girl named Lucky, who happens to be a lonely superstar trapped alone by her fame, it has gained haunting new meaning in light of Spears’ personal life in recent years. The Y2K classic clearly has left its impact on the current generation of pop girlies, with Taylor Swift covering the song, Meghan Trainor being inspired by it, and Halsey sampling it for a song in 2024.
The album also contains interludes of a giddy Spears ‘chatting’ on the phone with friends, gushing about cute boys and asserting herself. But Spears in the new Millennium was coming of age. So we do see a more feisty side of her emerge on songs like “Stronger”, "Don't Go Knockin' on My Door", "What U See (Is What U Get)". The songs give the album some much needed fire and funk, especially when Spears took to the road to promote it.
Oops!... holds a lot of nostalgic value for the generation of Millennials who grew up with it. It won’t be remembered as Spears’ strongest album, as her best works (and a lot of turmoil) was yet to come. But with a listen on its 20th anniversary, there is no denying the hooks are strong and that a young, joyful Spears was firing on all cylinders to make her mark on entertainment with it. And boy, did she do it again.
Also see: #review: Does Lady Gaga truly bring Mayhem with her new album?
