Inside Sean 'Diddy' Combs and Jay-Z's Decades-Long Friendship as They Both Face Rape Allegations

Sean "Diddy" Combs founded his record label, Bad Boy Entertainment, in 1993, about three years before Jay-Z debuted in the hip-hop industry with his album, Reasonable Doubt.

Following The Notorious B.I.G.'s murder in 1997, Combs channeled his heartbreak and grief into his debut album, No Way Out. Jay-Z was featured on one of the tracks, "Young G," marking the beginning of the twosome's constant collaboration.

After Combs dropped the material, he worked with Jay-Z on the latter's second album, In My Lifetime, Vol. 1, and co-wrote "I Know What Girls Like" alongside the billionaire rapper and Lil' Kim.

Combs and Jay-Z worked together again on the 1999 track, "Do You Like It… Do You Want It…" from the album Forever.

Their partnership continued, with the pair even performing together at events and shows.

They both hit lows in the late 1990s when they got embroiled in legal troubles.

In December 1999, Jay-Z was cuffed after he stabbed Lance "Un" Rivera at a Manhattan nightclub. Meanwhile, Combs and his then-girlfriend, Jennifer Lopez, got involved in a nightclub shooting but were both acquitted afterward.

After Hurricane Katrina wreaked havoc on New Orleans, Jay-Z and Combs made a joint donation of $1 million to the American Red Cross.

"This is our community. When I turn on CNN, I see a lot of black people on the streets. I know it's other people too, but those projects have been hit hard," Jay-Z said in a statement to the Associated Press at the time.

Combs added, "We are all descendants from each other's families. When you hear Black people say 'brothers' and 'sisters,' it's really true. These are all people that I know I'm related to somehow, some way — the human race family."

Jay-Z and Combs also socialized behind the cameras, often spending time together at parties.

In 2009, the "Can't Nobody Hold Me Down" singer commented on a photo of himself and Jay-Z at one of his birthday parties.

"I was just telling him I appreciate him coming," said Combs. "He was on tour, and he flew in private after one of his shows just to come to that party. Then he had to fly back out. I was just telling him how much I appreciated it and how much I value our friendship."

He added, "People see us as competitors and different icons in the hip hop game but that was just a moment of two Black brothers telling each other how much they appreciate each other."

They also partied with several stars — including Beyoncé, Kim Kardashian, Kanye West and Cassie Ventura — at an MTV Video Music Awards after-party in 2016.

Before Combs' scandal exploded, Jay-Z praised him when the "Coming Home" singer was given the Lifetime Achievement Award at the 2022 BET Awards.

“Here’s this guy from a neighborhood similar to where I grown up that made it to these unreachable heights,” Jay-Z said of Combs. “Puff was the first one that came through and made us feel like it was us.”

Combs was arrested on September 17 on racketeering and s-- trafficking charges.

Although Jay-Z remained silent about the allegations against Combs, he made headlines after a lawsuit implicated both men in the rape of a 13-year-old girl over two decades ago.

The plaintiff, identified as Jane Doe, alleged Jay-Z and Combs sexually assaulted her at an MTV Video Music Awards after-party in 2000. In the lawsuit, she claimed Jay-Z removed her clothes and raped her while Combs and an unidentified female celebrity watched.

Jay-Z's attorney Alex Spiro filed a motion to dismiss the rape lawsuit re-filed by Houston-based lawyer Tony Buzbee.

"Fair is fair. It is not consistent with justice, fairness, or the rules governing federal proceedings for the Plaintiff and her counsel to smear [Jay-Z]'s good name," Spiro wrote, requesting the court to deny the plaintiff's request to proceed anonymously.

The attorney also demanded Buzbee end his "sprawling extortion saga – [a] saga whose aim is base and measured in dollars."