A Look at Jay-Z, Diddy’s BFF Relationship Before The Bombshell Lawsuits

Sean Combs and Shawn Carter may not be “BFF’s” but they sure weren’t enemies.

Photo: Getty Images Kevin Mazur

Given the shocking lawsuit accusing both Shawn Carter, better known as Jay-Z, and Sean “Diddy” Combs, of raping a 13-year-old girl, folks have been wondering just how close the two were or how they even came to be colleagues over the years.

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Biggie and Diddy’s Strange Friendship: Revisiting the Most Defining Moments

The men are arguably two of the most powerful and influential moguls in the music industry, having emerged from Hip Hop, specifically. So their paths were bound to cross given the constant networking of the music scene.

Since the late 90s, you could find the two featured on each others songs, partying together, sitting court side at a basketball court or even having true, brotherly moments off stage. Through photos, let’s take a look at their friendship and collaborations over time:

“I Know What Girls Like” Song Collab (1997)

One of the earliest music collaborations between Jay-Z and Diddy was this track off the “In My Lifetime, Vol. 1″ album.

The Infamous 4th of July Party (2000)

Photo: Getty Images Patrick McMullan Photo: Getty Images Patrick McMullan

Jay-Z pictured at one of Diddy’s widely speculated “white parties,” cited in numerous sexual assault lawsuits for being the location of alleged sex parties, sexual assaults and sex trafficking.

Roller Bash CD Release Party (2000)

Photo: Getty Images Jeff Kravitz/FilmMagic, Inc Photo: Getty Images Jeff Kravitz/FilmMagic, Inc

The two are pictured at Jay-Z’s release party taping for MTV.

The Best of Both Worlds Announcement 2002

Photo: Getty Images Johnny Nunez/WireImage Photo: Getty Images Johnny Nunez/WireImage

Diddy was at the podium to help Jay-Z announce his collaborative album with R. Kelly, “The Best Of Both Worlds,” per USA TODAY.

Absolut White Party (2003)

Photo: Getty Images Dimitrios Kambouris/WireImage for Bad Boy Entertainment Photo: Getty Images Dimitrios Kambouris/WireImage for Bad Boy Entertainment

The two are pictured at another one of Diddy’s white parties at his home in East Hampton.

BET Relief Telethon (2005)

Photo: Getty Images Scott Gries Photo: Getty Images Scott Gries

The two hold a check for $1 million they pledged to donate to the American Red Cross during BET’s Relief Telethon to raise aid for Hurricane Katrina victims.

“American Gangster” Collaboration (2007)

Screenshot: YouTube Screenshot: YouTube

On Jay-Z’s tenth studio album, Diddy is featured as a producer on six tracks including songs “Roc Boys (And the Winner Is)…” and “American Dreamin.’”

Screamfest (2007)

Photo: Getty Images Scott Gries Photo: Getty Images Scott Gries

The two performed alongside one another at Madison Square Garden during Screamfest.

Barack Obama Rally (2008)

Photo: Getty Images Logan Fazio/FilmMagic Photo: Getty Images Logan Fazio/FilmMagic

The two joined one another to formally endorse former President Barack Obama for his first term at the “Last Chance For Change” Rally at Florida Memorial University.

Roc Nation’s Pre-Grammy Brunches Since 2011

Photo: Getty Images Kevin Mazur Photo: Getty Images Kevin Mazur

Diddy appeared to have frequented Jay-Z’s Roc Nation pre-Grammy’s brunch events. He went viral for a speech he gave at the 2020 event as Jay-Z seemingly stood awkwardly next to him.

“The game has been elevated. As we can tell, there’s no expense being spared. We at a Black billionaire’s lunch. We here together and we keep staying together. United we stand and ain’t nothing else,” he said ahead of a toast.

Yeezy Fashion Show (2015)

Photo: Getty Images Kevin Mazur Photo: Getty Images Kevin Mazur

The two sat side-by-side showing support for the Yeezy Season 1 fashion show during New York Fashion Week.

The Family Bad Boy Reunion Tour (2016)

Photo: Getty Images Jamie McCarthy Photo: Getty Images Jamie McCarthy

Jay-Z on stage with Diddy as the two perform at the Barclays Center for The Family Bad Boy Reunion Tour presented by Ciroc Vodka.

MTV VMA’s After Party (2016)

Photo: Getty Images James Devaney/GC Images Photo: Getty Images James Devaney/GC Images

Diddy and Jay-Z spotted at Pasquale Jones celebrating at a VMA’s afterparty.

Black Excellence (2017)

The two music moguls were seen in a behind-the-scenes compilation from the Roc Nation pre-Grammy’s Brunch from 2017, chatting, laughing and otherwise displaying a form of brotherhood.

Diddy’s 50th Birthday Party (2019)

Photo: Getty Images Kevin Mazur Photo: Getty Images Kevin Mazur

Jay-Z attended Diddy’s massive 50th birthday bash in Los Angeles.

DJ Khaled Hollywood Walk of Fame Star (2022)

Photo: Getty Images Kevin Winter Photo: Getty Images Kevin Winter

The two appeared alongside one another to support DJ Khaled when he was awarded his star on the Walk of Fame in Hollywood.

Diddy’s BET Lifetime Achievement Award (2022)

Photo: Getty Images Kevin Winter Photo: Getty Images Kevin Winter

Jay-Z contributed a taped tribute to Diddy to honor him for the BET Lifetime Achievement Award and his legacy in both music and the community.

Carpool Karaoke (2023)

Photo: Getty Images Terence Patrick/CBS Photo: Getty Images Terence Patrick/CBS

Diddy told James Corden on the Carpool Karaoke segment of “The Late Late Show” that his relationship with Jay-Z was of such high regard, the Roc Nation CEO was the only one besides his mother allowed to address him by his first name: Sean.

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