How Much Older Is Sean ‘Diddy’ Combs Than Kid Cudi?

Kid Cudi and Sean “Diddy” Combs represent two very different eras of hip-hop, yet their paths have crossed in more ways than one. Combs, who rose to prominence in the 1990s as a mogul shaping the sound and business of rap, embodies the glitz and dominance of hip-hop’s golden age of excess. Kid Cudi, meanwhile, carved out a lane in the late 2000s as a vulnerable, genre-blending artist whose introspection resonated with an entirely new generation. Cudi wrote about interactions he had with Combs in his memoir, Cudi: The Memoir. So, what is the age difference between Combs and Cudi? Here’s what to know.

What is Sean ‘Diddy’ Combs’ age compared to Kid Cudi’s?

Over the years, the famously complex relationship between Sean “Diddy” Combs and Kid Cudi has evolved from uneasy mutual respect into a fraught chapter defined by rivalry and trauma. In 2011, during Cudi’s brief romance with Casandra “Cassie” Ventura, Combs allegedly broke into the rapper’s Hollywood Hills home. Cudi found his family gifts unwrapped and his dog locked in a bathroom, a terrifying intrusion he later reported to the police. Then, in early 2012, Cudi’s Porsche was set ablaze, with prosecutors suggesting Combs may have orchestrated the attack and an assertion Cudi expressed he believed to be true. Cudi, who described hating every minute of testifying against Combs in court, ultimately took the stand to support Ventura.

Cudi testifying in Combs’ trial brought both hip-hop artists into the spotlight. And while they’re peers in the industry, they’re nowhere near the same age. Combs turns 56 years old in 2025. And Cudi turned 41 in January 2025. This makes Combs nearly 15 years Cudi’s senior.

As for Ventura, she is 39 years old — much closer to Cudi’s age than Combs’.

What age will Sean ‘Diddy’ Combs be once he leaves prison?

Sean “Diddy” Combs is scheduled to be sentenced on Oct. 3, 2025, following his conviction on two counts of violating the Mann Act, which prohibits the transportation of individuals across state lines for illicit sexual purposes. Although Combs was acquitted of more serious charges, including racketeering conspiracy and sex trafficking by force, fraud, or coercion, the prosecution has indicated that they will seek a sentence of at least 51 months (approximately 4.25 years).

CBS News reports that the defense has suggested a lesser range of time spent behind bars. They’re pushing for Combs to spend only 21 to 27 months in prison.

Ultimately, Combs can spend 20 years behind bars. But that seems like the most unlikely outcome.

If Combs receives four years in prison, he’ll likely leave when he’s 59-60.

Kid Cudi said he later ‘found peace’ after the hip-hop mogul apologized to him

While testifying under oath during Sean “Diddy” Combs’ trial, Kid Cudi noted that he “found peace” with Combs after Combs apologized to him in 2015.

“Man, I just want to apologize for everything and all that bullsh*t,” Cudi recalled that Combs said, according to WRAL News. “That was the last thing I was expecting to get from him,” Cudi said.

Ultimately, Cudi noted that he and Casandra “Cassie” Ventura broke up because of the drama involving Combs. He worried about his and Ventura’s safety because he “knew Sean Combs was violent.”

In August 2025, Cudi recalled how he was extremely upset when he was subpoenaed for the trial. However, once he reframed his testimony as helping Ventura, he was able to keep a level head.

“I thought about, you know, when I was up there, you know, I’m here to support Cassie,” Cudi said on the Call Her Daddy podcast. “And, you know, Cassie is my friend. And I love her, and I want to see her do well. When I saw her get married, I was so happy for her that she found someone, her person. When I saw she was having kids, I was like, ‘Oh, this is so awesome.’ You know what I mean? I’ve always just wanted to see her thrive and do well and be happy, because I know she was living a nightmare.”

For more news and exclusive interviews, follow Showbiz Cheat Sheet’s Instagram.