Dear Gossips,

Oops…I Did It Again.

Tomorrow is the 20th anniversary. On May 16, 2000 Britney Spears released her second album, and the title track became a monster hit; she was already, by that point, the biggest superstar in the world after the success of ...Baby One More Time. But as famous as she already was, Britney’s fame mountain was higher than most. And with Oops, she just kept climbing. 


Ahead of this two decade milestone, Jeff Weiss wrote a GREAT piece about the “planetary impact” of Oops and Britney at The Ringer. It’s one of those essays that takes you right back to where you were, an article you never want to end, about an era that had to end. He’s not talking necessarily about Britney here but more about what she represented in that time – as he puts it, the “gilded years of the record industry” and the “teen pop era”. Britney was its final, most powerful, golden child. 

And while, sure, there was team of collaborators who participated in creating her, this tribute to Britney and Oops leaves no doubt that Britney was the chief architect of Britney. Anyone who tells you different reveals themselves to be a pop culture amateur. But, sure, if you have the energy to educate them, send them this Ringer piece and its predecessor, the oral history of “…Baby One More Time” in Entertainment Weekly that was published in October 2018 to mark the then 20th anniversary of the birth of an icon. Because even those who deny Britney’s active involvement in her own genesis cannot deny that she is one of the most important cultural figures of our time. 

And she was so important in the spring of 2000 that… Leonardo DiCaprio was supposed to be in the “Oops I Did It Again” video! Allegedly. Not that she needed him, obviously. But the point here is the mythology. What is once an anecdote over time alchemises into legend. This happens with all the greats. Also, remember this? 


Leo, if you believe the story, was supposed to play the astronaut in the “Oops” video. Like I said, it didn’t make a difference. The video was bonkers and people went bonkers for it. And it’s not like you’ll ever forget the song or what’s probably its most famous lyric: “I’m not that innocent”. 

Which is not my favourite lyric on the track. My favourite lyric is “That is just so typically me”. God I f-cking loved that line the minute I heard it. Because the words hit so perfectly with the beat. And it’s the ultimate flex. It’s Britney’s version of “it’s not you, it’s me”. With those warm brown eyes and that pretty smile, delivered with a shrug. How could you be mad that she played with your heart?!


Sorry. I’ll get out of your way now. Because the only thing to do in this moment is to watch and remember. And then if you haven’t already, click here to read Jeff Weiss’s piece at The Ringer.

Yours in gossip,