Kanye West and JAY-Z made headlines in recent years for their tumultuous friendship

By Helen Murphy
December 15, 2019 04:30 PM

JAY-Z, 50, and West, 42, both attended the star-studded bash on Saturday night alongside their respective wives Beyoncé and Kim Kardashian West. In footage from the party, the two rappers could be seen talking and laughing with one another, and both also posed for a photo with Diddy and Pharrell Williams.

An insider told PEOPLE that the two rappers and their wives sat pretty close together during the festivities.

West and JAY-Z’s friendship began in the late ’90s when he was recruited to produce tracks for Roc-A-Fella Records, which was founded by JAY-Z, Damon Dash and Kareem “Biggs” Burke.

The two also collaborated on their 2011 joint album titled Watch the Throne, but their relationship became rocky after JAY-Z and Beyoncé, 38, did not attend West’s wedding to Kardashian West, 39.

Kanye West and JAY-Z
Kevin Mazur/Getty Images

Though Beyoncé sent well wishes to West and Kardashian West on their wedding day, the couple did not attend the fête in 2014. Two years later, West went on a rant during his concert, saying their daughters had yet to have a play date and neither Beyoncé nor JAY-Z checked in after Kardashian West’s Paris robbery.

JAY-Z called out West’s erratic behavior on his track “Kill JAY-Z,” and the two also battled over a money dispute involving Tidal.

“What really hurt me, you can’t bring my kid or my wife into it,” JAY-Z later said in a radio interview. “We’ve gotten past bigger issues, but you brought my family into it, now it’s a problem with me.”

The “99 Problems” rapper added: “You know it’s a problem because me and him would have been talked about it, been resolved our issues. And he knows crossed the line. He knows. And I know he knows. ‘Cause we’ve never let this much space go between one of our disagreements and we’ve had many. That’s part of who we are.”

Pharrell Williams, Kanye West, Sean “Diddy” Combs, and JAY-Z
Kevin Mazur/Getty Images

In 2017, however, JAY-Z revealed the duo were back on speaking terms. “He’s my brother,” he told T, The New York Times Style Magazine. “I love Kanye. I do. It’s a complicated relationship with us… It’s just that there’s certain things that happened that’s not really acceptable to me. And we just need to speak about it. But there’s genuine love there.”

West acknowledged in 2018 that he was “hurt” by their lack of attendance on his wedding day. “I understand they were going through some things, but if it’s family, you’re not going to miss a wedding,” he said. Later that year, he posted a photo of JAY-Z and Beyoncé, calling them “famleeeeee,” seemingly showing they were still on good terms.

Earlier this year, West sued JAY-Z’s Roc-A-Fella Records, claiming he was owed money.

Kanye West and Kim Kardashian West at Diddy’s birthday party
Kevin Mazur/Getty Images

Other celebrities in attendance at Diddy’s bash on Saturday night included Naomi Campbell, Cardi B and husband Offset, members of the Kardashian-Jenner family, as well as Usher, Leonardo DiCaprio, Lil Kim and Mary J. Blige.

A source told PEOPLE of the bash: “It was like a superstar convention! The musical giants of our time were all there to pay their respects.”