Sean “Diddy” Combs and Jay-Z (real name Shawn Carter) are rappers, record moguls and old pals whose friendship dates all the way back to the ’90s.
The men collaborated on several projects, supported one another’s careers and praised each other publicly before Jay-Z was accused of raping a 13-year-old girl with Diddy in a recently amended lawsuit, in which the unnamed female — known as Jane Doe — claimed the rappers took turns assaulting her at an afterparty following the 2000 Video Music Awards.
Jay-Z denied the “heinous” allegations, calling the lawsuit a “blackmail attempt.”
Here’s a look back at Diddy and Jay-Z’s decades-long friendship.
1997 — Diddy and Jay-Z collaborate for the first time
The pair collaborated on each other’s 1997 albums following the death of their mutual friend Notorious B.I.G. (aka Biggie Smalls, real name Christopher George Latore Wallace). Diddy featured Jay-Z on the track “Do You Like It, Do You Want It” from his “No Way Out” album, while Combs appeared on “In My Lifetime, Vol 1,” Carter’s second album.
When he died, Biggie was signed to Diddy’s record label and had previously collaborated on Jay-Z’s first album, “Reasonable Doubt.
1999 — Diddy and Jay-Z get into trouble for separate events
The rappers found their names splashed across the news following two separate events in 1999. Jay-Z received three years of probation for his role in the stabbing of Lance “Un” Rivera at the Kit Kat Club in New York. Two decades later, Rivera confirmed that “Jay-Z was not the guy who actually stabbed me that night.”
Diddy also received three years of probation for fleeing the scene of a nightclub shooting near Times Square with his then-girlfriend Jennifer Lopez.
It’s believed Diddy and Jay-Z bonded over their experiences.
2003 — Diddy teams up with Jay-Z’s then-girlfriend, Beyoncé
Jay-Z and Beyoncé were linked in 2001 when he was 33 and she was 19. During that time, the pair regularly mingled with Diddy at Hollywood events. Less than a decade after collaborating with Jay-Z, Diddy joined forces with Beyoncé on her 2003 hit “Summertime.”
September 2005 — Diddy and Jay-Z donate $1 million
The rappers jointly donated $1 million to the Hurricane Katrina relief fund. Diddy and Jay-Z presented their large check during a live telethon.
August 2007 — Diddy spanks Jay-Z twice during hip-hop festival
During their summer 2007 Screamfest festival performance, Diddy was filmed slapping Jay-Z on the butt two times, according to Us Weekly.
June 2009 — Diddy calls Jay-Z his ‘Black brother’ and Kim Porter jokes about a ‘secret society’
Diddy addressed his close friendship with Jay-Z after several party pictures of the pair and other music industry A-listers were featured at The Rock N Roll Of Hip Hop exhibition in Beverly Hills. Diddy spoke with Young Hollywood at the time about one image showing the two men chatting at one of his infamous birthday parties.
“I was telling him how much I appreciate him coming…” Diddy said. “And how much I value our friendship. 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.”
Kim Porter, who was by Diddy’s side at the event, chimed in with a smile. “We call that picture a secret society, all we ask is trust!” she quipped. Porter died from pneumonia in 2018 at 47.
2012 — Diddy and Jay-Z land on Forbes’ wealthiest list
The men’s careers seemed to mirror each other, with Diddy and Jay-Z dominating Forbes’ list of wealthiest hip-hop artists in 2012. Diddy landed the top spot with an estimated personal fortune of $550 million thanks to his Sean John clothing line, stakes in a vodka company and record label. Jay-Z came in second at $460 million.
August 2016 — MTV Video Music Awards afterparty
Diddy and Jay-Z celebrated alongside their ladies (Cassie Ventura and Beyoncé) at an afterparty in New York following the MTV Video Music Awards and several other A-listers, including Kim Kardashian and her then-husband, Kanye West.
January 2020 — Black Billionaire Brunch
Diddy and Jay-Z kicked off 2020 at the Black Billionaire brunch hosted by Roc Nation. Diddy made a toast at the event as Jay-Z smiled and nodded along.
“It’s 2020, y’all, and it is different than when it was 2016,” Diddy said. “The game has been elevated. As you know, there has no expense been spared. We had a Black billionaire lunch year, understand, right? And, we’re here together in keeping staying together. We’re getting tighter, and united we stand.”
April 2022 — Hollywood Walk of Fame
Diddy and Jay-Z chummed it up when DJ Khaled was honored with a star on the Hollywood Walk of Fame. The pair — dressed in all-black — joked around as they sat next to each other in the front row and even posed for photos together.
June 2022 — Diddy’s Lifetime Achievement Award
When Diddy received the Lifetime Achievement Award at the 2022 BET Awards, Jay-Z was among the stars who sang his praises in a video montage honoring his career.
“Here’s this guy from a neighborhood similar to where I grown up that made it to these unreachable heights,” Jay-Z gushed about Diddy. “Puff was the first one that came through and made us feel like it was us.”
March 2024 — Jay-Z stays quiet as accusations mount against Diddy
50 Cent poked fun at Jay-Z, claiming he must be “missing” or “in hiding” because he hadn’t spoken out about the allegations against Diddy. The “Bad Boy for Life” rapper was arrested in Sept. on charges of sex trafficking, racketeering and transportation to engage in prostitution after several accusers — both men and women — stepped forward with lawsuits, sparking a grand jury indictment. Diddy has denied the allegations against him.
December 2024 — Diddy and Jay-Z named in rape lawsuit
In a recently amended civil lawsuit, a “Jane Doe” accused Diddy and Jay-Z of raping her in 2000 when she was just 13 years old at an afterparty following the MTV Video Music Awards in 2000.
Jane Doe claimed the rappers allegedly took turns raping her at a residence while an unnamed female celebrity watched after she was drugged.
Jay-Z denied the “heinous” allegations, calling the lawsuit a “blackmail attempt,” and stepped out with his family in the wake of the legal battle. Diddy is currently behind bars awaiting his sex trafficking trial, scheduled for May 5, 2025.
