Diddy went live on Instagram this weekend for a dance-a-thon fundraiser in support of COVID-19 healthcare workers in underserved communities and also served up some gossip nostalgia. Like I’ve been saying, I know that the popular narrative is that celebrities have been sh-t during the lockdown, there’s also been a recalibration. I mean, yes, of course, the tone-deaf posts are always going to happen (because they are CELEBRITIES, after all), but many have started to figure out what’s working, what people are responding to, and delivering accordingly. 

 

Diddy delivered the nostalgia and multiple fronts. Let’s start with … Jennifer Lopez!

Before we begin with the 2020 version of Diddy and JLo, of course we have to revisit this moment – from February 2000, so basically 20 years ago: 

Jennifer Lopez and Puff Daddy at the 42nd Annual Grammy Awards, February 23, 2000. K Mazur/ Getty Images
Jennifer Lopez and Puff Daddy at the 42nd Annual Grammy Awards, February 23, 2000. K Mazur/ Getty Images

That’s the iconic photo that everyone remembers. It’s the outfit, obviously. You know the outfit I prefer though? This one, from the MTV VMAs six months after the Grammys: 

Jennifer Lopez and Puff Daddy at the MTV Video Music Awards, September 7, 2000. Steve Azzara/ Getty Images
Jennifer Lopez and Puff Daddy at the MTV Video Music Awards, September 7, 2000. Steve Azzara/ Getty Images

That’s the look that is so specifically of the era, I’ll never be tired of it – the headband, the crop tank, the belt, the low rise, right now, it’s almost comforting. 

Not that this is the first time JLo and Diddy have publicly performed their friendship since they broke up. It’s not breaking news. But because they were such a great gossip story, it’s tapping into those memories. And she’s tapping into them too. Because you hear her talking about his dance moves, and how she probably taught him. 

Then, naturally, guess who had to make an appearance? As if Alex Rodriguez could resist – and then, when he was there, JLo had to get him into the conversation, sharing with Diddy, and the rest of us, that ARod is Diddy’s biggest fanboy. 

I mean, no one was asking but sure. 

 

So that’s two JLo love connections so far. Along came a third…although I feel like Drake remembers JLo a lot more – and differently – than she remembers him. It was two weeks! Barely! That prom night though! 

LOLOLOLOLOL. This moment in Gossip Nostalgia is brought to you by 2016. 

Anyway, at one point, Drake also popped in on Diddy’s dance-a-thon as he did the “Toosie Slide” with Diddy and his kids – along with everyone else the last week on TikTok: 

They also talked about music and Drake says that practising social distancing has meant that he’s been able to focus on the new album a lot more. Apparently he’s sitting on a LOT of songs, and this is the most “excited he’s been about an album in a long time”. Just in case you were, like, worried that COVID-19 would stall Drake’s career and plans – he’s going to be fine, OK, everyone? Drake is gonna be fine. 

 

Especially now that Diddy just declared that he’s in his Top 5 Rappers of all time: 

It’s the never-ending debate, and it exists across cultural streams. Top 5 or Top 3 basketball players, soccer players, hockey players, Call of Duty players, Game of Thrones players. But Diddy isn’t just some random making a list on Twitter. Diddy is Bad Boy, Diddy’s a godfather to a generation in his own right. So his pronouncement carries a lot more weight. And it definitely would to Drake. Who is, like Diddy, on his way to becoming a billionaire in his own right – and probably at a quicker pace. One day it’ll be Drake making a similar declaration. Who will it be that he anoints? And, God, who will WE be then?