Ranked: Britney Spears’ “Oops!… I Did It Again”

Vincent Anthony
9 Min Read

“Oops!… I did it again, I played with your heart, got lost in the game…”
–Britney Spears

The title track and stratospheric lead single from Britney Spears’ sophomore album, “Oops!… I Did It Again” might be directed toward a silly boy, but with this song and its parent album, breaking a boy’s heart became, in retrospect, a metaphor for much more. Released on May 16, 2000, the album is quintessential Y2K pop. With Oops!, she set the record for the biggest first week sales of any female artist (1,319,193, broken by Adele’s 25 in 2015); Britney Spears was the maven of the movement.

Upon Britney’s debut, we witnessed only the tip of what she was capable of. With her debut single in 1998 and album in 1999, she forever changed the course of Y2K Pop by becoming the Pop Princess that single handedly stared down a boatful of boy bands and girl groups. Imitators quickly followed, but they were mere stones in the shadow of the mountainous Britney Spears. In 2000, the enormity of her power was revealed. Her debut album …Baby One More Time served as a warning (“iceberg, straight ahead!”), but with her sophomore set, Britney Spears was revealed to be the iceberg that sank the titanic of her Y2K Pop peers.

In its wake, her competitors struggled to stay afloat. The Backstreet Boys went into hiatus following what would become their last successful album Black & Blue. *N’SYNC disbanded after their 2001 album Celebrity in light of Justin Timberlake’s solo ambitions. The Spice Girls released their final album, sans Ginger, Forever, in 2000. Competing princesses in waiting like Jessica Simpson and Mandy Moore enjoyed brief but fleeting success. Christina Aguilera‘s egotistical three year wait to follow up her hugely successful debut rendered 2002’s Stripped as her last successful album. P!nk cleverly defined herself as the rebellious anti-Britney, forging her own divergent path away from Y2K Pop. Destiny’s Child announced a hiatus for solo projects after the release of their 2001 Pop/R&B hybrid crossover album Survivor, making way for the rise of Beyoncé.

While all her peers either melted, or morphed to stay afloat, Britney Spears remained unscathed, resting upon her foundation as the reigning Princess of Pop. She continued to have hit after hit (such as two #1 singles in 2011), and even a Platinum single from her most recent album (2016’s “Make Me”). Ever humble, she’d never say it herself, but her motto could easily be: “Oops!… I Did It Again.”

Even in the face of her well-publicized struggles, Britney may have lost her status as the it-girl, but only because she eventually transitioned from girl to woman, from Princess to Queen. Her days of huge hit singles and monstrous albums may be behind her, but her title remains: Queen of Pop. Until her next hit single, let’s enjoy the classic “Oops!… I Did It Again.”

Britney Spears’ Oops!… I Did It Again, ranked.

In celebration of the album, I’ve spent a few days listening to it (and Britney in general) and ranked the songs from my least to most favorite. It was certainly a fun experience to relive this classic album. I felt myself transported back to 2000, when I was 9 going on 10, listening to music on my Discman before the prominence of mp3s and iPods that loomed around the corner.

The Syrupy-Sweet Ballads

Britney’s biggest fans may feel differently, but generally speaking when I think Britney Spears, ballads such as these are not my go-to. Her forte is genre-melding dance-pop; catchy melodies and anthemic lyrics. Syrupy sweet, dated ballads – not so much. The Shania Twain penned single “Don’t Let Me Be the Last to Know” is an adorable piece of pop, but not a highlight. Still, they are enjoyable moments within the context of the album. Shout out to Britney for garnering her first songwriting for “Dear Diary,” as well.

12. “Don’t Let Me Be the Last to Know”
11. “Where Are You Now”
10. “Dear Diary”

Millennial Moments

All album tracks, these bops are 100% Y2K, and products of the very Swedish team behind Britney’s beginnings. They’re all such fun songs, catchy and perfect sonic captures of the time. However, in comparison to my top 4 songs from the album, they don’t have the same resounding nostalgia. Though, “What U See (Is What U Get)” is definitely a personal favorite. I recall many moments jamming to that song via my Discman in 2000.

9. “One Kiss From You”
8. “Can’t Make You Love Me”
7. “Don’t Go Knockin’ on My Door”
6. “What U See (Is What U Get)”

5. “When Your Eyes Say It”

Upon re-listening to this album in its entirety to write about it, this song became a standout for me. It gives a hint of the more matured, sultry sounds Britney would explore beginning with 2001’s Britney and 2003’s In the Zone. No surprise as to why it stands out, the song is penned by Diane Warren; one of the few non-Swedish contributors to the set. Check out this adorable video of Britney recording the song:

The Iconic Singles

4. “Lucky”

Of course, “Lucky” is a classic offering from this set. Perhaps more so for its video, “Lucky” is one of those unforgettable Y2K Pop moments. The song itself is no masterpiece, but nevertheless it’s relatable and the perfect karaoke song.

3. “(I Can’t Get No) Satisfaction”

Beginning a trend of rock-n-roll covers for Britney, “(I Can’t Get No) Satisfaction” is also, surprisingly, a collaboration with turn of the century (and beyond) hitmaker Rodney “Darkchild” Jerkins. It’s also a nice showing of Britney’s vocal talent and versatility.

2. “Oops!… I Did It Again”

The iconic lead single and its out-of-this-world music video defined a generation. From the random Titanic reference in the spoken bridge, to its Martian setting, red latex jumpsuits, pyrotechnics and lyrical allusion to “…Baby One More Time,” the song is pure pop brilliance, and the video is part of pop culture history, defining for the TRL generation.

1. “Stronger”

Whether you love it for the iconic, Janet Jackson-inspired chair routine in its video, or just for its empowering and anthemic message, “Stronger” might have been overshadowed by the album’s namesake then, but “Stronger” has perhaps endured the best over time. Certainly a staple on any good gay bar’s playlist, “Stronger” is what Christina wishes “Fighter” was: an anthem for the gays and anyone else who has ever faced some sort of struggles in their life.

While its title track provides a long-standing motto for Britney and her professional successes, “Stronger” provides the motto not only for Britney’s own personal victories, but for anyone who has ever loved her music. In celebration of “Oops!… I Did it Again,” let’s all face it, who hasn’t?

Listen to Britney Spears’ ‘Oops… I Did It Again”

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Vincent is the founder of the magazine and has had a strong passion for popular music since, well, 1997! If it's not obvious, his favorite artists include Destiny's Child, Mariah Carey, Janet Jackson, Michael Jackson, P!nk, and many more. Vincent lives in New York, where he is a high school English teacher, and currently he is pursuing a Master's in Journalism at the Craig Newmark Graduate School of Journalism at CUNY.