Diddy has the fortune of having been around some of the greatest musicians of our time, and two that come to mind specifically following his recent post on Instagram are New York's eternal rap king The Notorious B.I.G. and the forever Princess Of R&B, Aaliyah.  

Diddy Puff Daddy Aaliyah Biggie The Notorious B.I.G.
Image: Spencer Platt/Getty Images 

Puff had a pretty illustrious history with both hip-hop icons. Many people don't know this, but Aaliyah was on the hunt for a musical family following her deplorable ordeal and split from R. Kelly at the end of 1994. She almost ended up at both So So Def and Bad Boy Records before finding a lane for herself within Timbaland and Missy Elliott's burgeoning Da Bassment Crew, also referred to as The Superfriends, and she even recorded a few demos in Trinidad with Diddy that he unfortunately lost. They remained cool as industry friends up until her death in a plane crash on August 25, 2001, with Puffy even attending her notoriously lavish NYC funeral on August 31, 2001 (seen above).

As far as B.I.G. is concerned, there's no mentioning Biggie without Puffy and vice versa. No one has done more to preserve Big Poppa's legacy quite like his old partner in crime Puff, and over the years he has shown that a million times over. From the Biggie Duets album all the way to helping craft BIG's 2009 biopic Notorious, it's clear that Diddy will never forget his eternal best friend and former Bad Boy business partner.

"I love this picture !!!" is all that Diddy wrote to caption the throwback flick, which was taken in December 1994 at a music festival event called "Hot Night" thrown in Montego Bay, Jamaica. Puffy would've been 25 years old, Babygirl would've been just that at 15 years old and Biggie was 22 years old in this photo at hand. Everyone from Lil Kim and Nicki Minaj to Fabolous and Big Sean agreed on the legendary status of this classic shot in the comments, and we just wish both legends were here to comment in nostalgic bliss right along with the rest of us. 

Rest in peace forever to both Biggie and Aaliyah. Peep Diddy's #FlashbackFriday flick below: