Inside Jay-Z and Sean 'Diddy' Combs' Decades-Long Friendship — From How They Both Avoided Jail Time to Infamous Butt-Slapping and Champagne Parties

Rap giant Jay-Z has a decades-long friendship with fallen mogul Sean Combs that was forged as they made their names and fortunes in the music industry

The pair even dodged jail time as they were caught up in a stabbing and a shooting, then there was the infamous butt slapping video, and footage of Jay-Z pledging his loyalty to his friend as the rest of Hollywood was distancing themselves from Combs, RadarOnline.com can reveal.

Jay-Z was also a guest of honor at Combs' star-studded 50th birthday bash in Beverly Hills in 2019 and he and his wife Beyonce were regulars at his white party bashes.

And just two years ago, Combs and Jay stood by DJ Khaled as he was honored with a star on the Hollywood Walk of Fame and were spotted chatting during the ceremony.

Caged Combs and Jay-Z’s friendship traces back to the 1990s when both artists made their mark in the music industry. Despite the competitive nature of hip-hop, Combs and Jay found common ground in their shared ambition and passion for music.

In 1997, the pair collaborated on a track that landed on No Way Out, Combs' debut studio album. Around that time, both of their careers were subject to controversy.

The rappers found themselves in legal turmoil in 1999, and they were facing the same amount of time in jail.

Jay was facing charges for stabbing Lance "Un" Rivera. Meanwhile, Combs was on the hook for his involvement in the infamous club shooting, which saw him flee the scene of a Times Square hotspot alongside Jennifer Lopez.

Both men avoided jail time, and their friendship continued to grow.

Combs and Jay-Z remained friends into the new millennium, and their bond seemed unharmed by their previous legal troubles. They were often spotted out together, and they regularly voiced support for each other in public.

However, an incident that occurred in 2007 has resurfaced amid assault allegations against Diddy. In a video from a performance at Screamfest ’07, Diddy appears to touch Jay’s butt, but the exchange is hard to make out.

That did not stop rap rival 50 Cent from using the clip to drag Jay into the drama and 50 took to Instagram in November 2023 to troll the pair, suggesting that Combs intentionally slapped Jay-Z’s butt.

Combs showed love to the Brooklyn native during an appearance on Sway In The Morning and revealed that they had plans to go into business together.

"Me and Jay, we’ve talked about it. We said we want to pick the best one," Combs explained. "It’s going to have to be that one thing that gets it all the way popping."

Now a video is being widely circulated on the web that shows Combs and Jay-Z along with their friends attending a Black Billionaires' lunch and pledging solidarity.

What's notable is that this get-together happened in 2020, a time when Hollywood seemed to be turning away from Combs. This renewed focus on their friendship has raised eyebrows, especially considering the ongoing controversies surrounding Combs.

In the video, Combs is seen addressing a group of his friends: "It's 2020, y'all, and it is different than when it was 2016. The game has been elevated. As you know, there has no expense been spared.

"We had a Black Billionaires' lunch year, understand, right? And, we're here together in keeping staying together. We're getting tighter, and united we stand," he says, before raising a toast to "us".

The group is then seen breaking into big cheers and laughter as they enjoy their drinks.

Now rape-accused Jay-Z is bracing himself for a brutal "emergency" sit-down with Beyoncé and their three children to explain a civil lawsuit that sensationally accuses him of sexually assaulting a drugged 13-year-old girl with Combs.

The 99 Problems rapper-turned business mogul was sent "reeling" by the allegation, which came from an accuser who identifies herself only as Jane Doe in the legal documents.

She claims the rape took place at a party after the 2000 MTV Video Music Awards and also involved a female celebrity who allegedly stood by and watched her be brutalized.

Her lawsuit was first lodged at New York's Southern District in October against Combs, but a new refiling made on Sunday December 8 named 55-year-old Jay-Z, born Shawn Carter, as the other celebrity allegedly involved in the attack.

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