Jay-Z and Diddy’s Friendship Timeline: Hip-Hop Rivalry, Collabs, Diddy’s Legal Troubles

Jay-Z and Sean “Diddy” Combs faced ups and downs while building their successful hip-hop empires.

Running in similar industry circles since the ‘90s — when Diddy and Jay-Z launched Bad Boy Records and Roc-A-Fella Records, respectively, in New York City — the pair formed a friendly rivalry as their individual music careers took off.

Over the years, the music moguls joined forces, collaborating on several projects together and supporting one another away from the mic by praising one another publicly. Their connection came under scrutiny in late 2024, however, when Jay-Z was accused of rape in a civil lawsuit alongside Diddy. Per NBC News, the accuser — who remained anonymous and was referred to as “Jane Doe” — was 13 years old when the alleged incident occurred in 2000. (Jay-Z called out the “heinous” accusations in a December 2024 statement.)

Keep reading for a look back at Diddy and Jay-Z’s history through the years:

1996

While Diddy was already a well-known music mogul, Jay-Z was finding success with his first album, Reasonable Doubt, which featured the late Biggie Smalls. The Notorious B.I.G was signed to Diddy’s label.

1997

Following the murder of their mutual friend Smalls, Diddy agreed to collaborate with Jay-Z on his second album, In My Lifetime, Vol 1. They also worked together on the track “Do You Like It, Do You Want It” from Diddy’s No Way Out album.

Years later, Diddy said that he saw Jay-Z filling the space that Smalls and the late Tupac Shakur had left behind.

1999

Jay-Z faced jail time for his role in the stabbing of Lance “Un” Rivera at the Kit Kat Club in New York. He received a three-year probation, and Rivera confirmed two decades later, “Jay-Z was not the guy who actually stabbed me that night.”

Diddy, meanwhile, received a three-year probation for fleeing the scene of a nightclub shooting near Times Square with Jennifer Lopez.

Both relieved to escape prison time, the two rappers bonded over their experience.

Early 2000s

Beyoncé Knowles, then 19, and Jay-Z, 33 at the time, began dating after forming a friendship. The couple and Diddy were often seen attending each other’s professional events and enthusing about their mutual success.

2003

Beyoncé, now a huge solo artist after Destiny’s Child disband, collaborated with Diddy on the song “Summertime.”

September 2005

Diddy and Jay-Z jointly donate $1 million to the Hurricane Katrina relief fund, presenting a huge check during a live telethon.

August 2007

Diddy and Jay-Z performed together at Screamfest, a touring hip-hop festival, and Diddy was filmed slapping Jay-Z twice on the butt.

June 2009

Photos of Diddy partying with Jay-Z and other friends from the music industry were featured at The Rock N Roll Of Hip Hop exhibition in Hollywood. Diddy spoke on camera about a picture showing the two men talking at one of his birthday parties. “I was telling him how much I appreciate him coming…” he 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.”

Diddy’s ex Kim Porter, who died in 2018, added with a smile: “We call that picture a secret society, all we ask is trust!”

2010

Jay-Z and Diddy both topped Forbes’ list of wealthiest hip-hop artists, asserting their dominance in music and business. They publicly celebrated each other’s achievements and were featured high on the list for several years.

August 2016

The pair partied with stars including Beyoncé, Kim Kardashian, Kanye West and Cassie at an MTV Video Music Awards afterparty in New York.

January 2020

Diddy and Jay-Z toasted their careers at a Black Billionaire brunch hosted by Roc Nation. “It’s 2020, y’all, and it is different than when it was 2016,” Diddy said at the event, with Jay-Z nodding along. “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

The duo hung out together and posed for photos as they celebrated DJ Khaled being honored with a star on the Hollywood Walk of Fame.

June 2022

Diddy received the Lifetime Achievement Award at the 2022 BET Awards, and Jay-Z appeared in the video montage paying tribute to his work in music. “Here’s this guy from a neighborhood similar to where I grown up that made it to these unreachable heights,” he said. “Puff was the first one that came through and made us feel like it was us.”

March 2024

As accusations mount up against Diddy, fellow hip-hop star 50 Cent shared a controversial Instagram image, joking that Jay-Z must be “missing” or “in hiding” because he hasn’t spoken out about Diddy. (Multiple men and women alleged they were sexually assaulted by Diddy, who was eventually arrested in September 2024 following a grand jury indictment. He has denied all claims.)

December 2024

Jay-Z was accused, alongside Diddy, of raping a 13-year-old after the 2000 MTV Music Video Awards. Jay-Z fiercely denied the claims, issuing a statement alleging he was being blackmailed. The accuser’s attorney, however, claimed she never “demanded a penny” from the rapper.