Biggie’s Legacy, Diddy’s Villain Era: Their Strange Friendship Through the Years, Explained

May 21 marks what would’ve been the 53rd birthday of Christopher Wallace, better known as The Notorious B.I.G.—the Brooklyn-born rapper whose voice, flow, and storytelling changed the face of hip-hop forever.

And while fans around the world continue to celebrate his legacy, it’s impossible to talk about Biggie without also talking about Sean “Diddy” Combs, the Bad Boy Records mogul who helped launch his career—and who now finds himself at the center of multiple sexual assault lawsuits and a federal sex trafficking trial.

The relationship between Biggie and Diddy was always layered with it being part business, part brotherhood, and full of ups and downs. Over the decades, Diddy has painted himself as the steward of Biggie’s legacy, but public sentiment has shifted—especially in light of recent headlines.

So today, as we honor Biggie’s life and impact, we’re revisiting some of the most defining moments between him and Diddy that show just how deep—and complicated—their connection really was. Keep reading to get into it all!

Diddy’s Discovery of Biggie Gets Off to a Rocky Start

Known then as Sean “Puffy” Combs who was working as an A&R executive at Uptown Records, he discovered a young Christopher Wallace from Brooklyn in in 1992. Impressed by his gritty delivery and raw talent, Diddy signed him almost immediately. But just as things started rolling, Uptown fired Diddy, leaving the young rapper’s future temporarily in limbo.

However, this moment would ultimately birth Bad Boy Records—and set the tone for a historic loyalty between the two.

Bad Boy Records Is Founded With Biggie as Main Act

As the Bad Boy Records ball began rolling, Biggie emerged as the flagship artist and quickly became the face of the label’s gritty East Coast aesthetic. While Biggie was front and center (with Diddy not too far behind him, as shown in multiple music videos) Diddy handled the behind the scenes money and marketing moves—kicking off their rise to stardom in a positive direction.

Biggie and Tupac Shakur Become Friends, Signaling the First Rift in Biggie and Diddy’s Relationship

Despite Biggie and Diddy’s budding success and friendship, things started to take a turn when it the “Big Poppa” star befriended West Coast rapper Tupac. Even though Pac and Diddy never really had any issues on the surface, due to some underlying issues between the Bad Boy Records founder business dealings and Biggie’s growing weariness of them—this newfound brotherhood between the “Hypnotize” and “Keep Ya Head Up” rappers would prove to be an early wedge.

Below the surface however, it was reported that Tupac wasn’t a fan of Diddy and that the Bad Boy mogul also held some secret jealousy against Pac, as noted by former Bad Boy co-founder and president Kirk Burrowes in an interview with Rolling Stone.

“Ready to Die” Changes the Game and Diddy Pushes Biggie to Be a Bigger Star

One of the more positive moments of their friendship was when Biggie’s debut album, “Ready to Die,” exploded onto the scene in September 1994. It instantly cemented him as the East Coast’s rap king thanks to radio staples like “Juicy” and “Big Poppa.” This quickly turned the once budding rapper into a household name—and consequently turned Diddy into a hit-making mogul.

The East Coast vs. West Coast Rap Rivalry Drives Wedge Between Diddy and Biggie

As the faces of Bad Boy Records and East Coast rap, Diddy and Biggie became major players in the escalating beef against Death Row Records and the West Coast, fueled by media, miscommunication, and ego. Despite Biggie’s claims that he had no beef with Tupac, the narrative around their rivalry exploded, pulling both him and Diddy deeper into the drama. (The 1994 Quad studios shooting and subsequent song releases didn’t help, either).

As a result, their Biggie’s friendship with both Pac and Diddy was tested under the weight of music politics and public pressure, and it would eventually lead to two out of the three paying the ultimate price.

Biggie and Diddy’s Relationship Hits A Wall Over Publishing Rights

Though it would be decades later before this tidbit was revealed, months before Biggie’s shocking death in 1997, he was allegedly trying to get out from under his Bad Boy contract citing issues with his publishing rights. According to hip-hop photographer Monique Bunn in an interview for Rolling Stone, Biggie told her way back when that his plan was to leave Diddy and the label because the legal fight to get his music rights back was beginning to become too much.

Diddy Pulls Weird Move After Biggie’s Death

According to Burrowes, not too long after Biggie’s death via drive-by shooting in 1997, the label was approached to see about putting the “Big Poppa” star on the cover of Rolling Stone as a way to honor his legacy. However, that didn’t end up happening because Diddy reportedly took the cover spot himself in an attempt to promote his own forthcoming album at the time, “No Way Out.”

Weird move to pull for your “brother,” but OK.

“I’ll Be Missing You” Garners Mixed Fan Reactions

Just two months after Biggie’s death, Diddy released “I’ll Be Missing You” with Faith Evans and 112, a tribute that dominated the airwaves. The song was a success, proving Diddy’s own talent as a solo artist and music icon seemingly overnight. However, folks were split: while some viewed the song as heartfelt, others felt it was just an opportunistic move.

Diddy’s “No Way Out Tour” Feels A Bit Off

After Biggie’s death, Diddy hit the road not too long after for his “No Way Out” tour, which featured Mase, The LOX, Usher, Jay-Z, Faith Evans and more. Though the shows were enjoyable, there was a noticeable void without Biggie at center stage as he worked closely with Diddy on putting the album together before his untimely death. And while Diddy reportedly paid tribute to him during the shows, it still left a sour taste in some fans’ mouths who once again questioned Diddy’s motives behind it all.

“The Notorious B.I.G.: Born Again” Drops to Mixed Reactions

Two years after Biggie’s death, his first posthumous album dropped, produced by Bad Boy Records. While some listeners and critics thought the project was a good body of work tat did well to match the “Juicy” rapper’s artistry with modern sounds—others felt like it was just another attempt by Diddy to capitalize off his friend’s death.

Diddy and Biggie’s Mother’s Relationship Sours

In the years since Biggie’s death, the friendship between his mom—Voletta Wallace—and Diddy became strained over Wallace’s feelings that the Bad Boy producer wasn’t doing right by her son’s legacy. She said as much in her 2005 memoir, writing at the time:

“My son was part of a high-stakes game and didn’t know the rules. I’m glad he does not have to witness that the very people that he thought he could ride and die with wouldn’t think twice about using his mother. I am glad that he’s not here to see how they have used his image and his name.”

Wallace also added that Combs really only “loved” her son “after he was dead.”