Gossip in Photos

The celebrity photos that we’ll never forget – especially THAT one.

What are some of our all time favourite photos? (MediaPunch/Shutterstock)

Dear Squawkers,

We got a question last week for the mailbag and the answer turned into its own newsletter because we cheated and couldn’t keep it to just one classic celebrity photo. But how could we possibly narrow it down to just one? So here’s the nostalgia, as told through a series of famous images – and most of you should know all of them, although I’m curious to see whether or not there will be a few of you who’ll be introduced to our penultimate pick because, like not to brag, but I feel like I was the only gossip site at the time fixated on this picture and I can’t understand why more people weren’t and aren’t What The Fucking it all the time?!

So here’s the question that inspired this piece.

Question from Ketri:

What’s your favourite celebrity gossip related photo of all time? Anything goes - photoshoot, red carpet, pap shot, whatever!

Lainey’s Answer:

Thank you for your question, this is SO MUCH FUN. But, as noted above, how do you expect me to choose just one? No, we’re going through a few of them. Starting with… 

Britney Spears and Justin Timberlake, the American Music Awards, 2001. No, we don’t fuck with JT here, but if we’re talking about memorable celebrity photos, photos that have been branded onto our gossip brains, the ones we would still be able to describe on our death beds, this one has to make the list. No one was more famous than Britney at the time of this shot. No couple better captured the gossip zeitgeist at the time of this shot. And these fucking outfits…