Controversial music mogul Diddy appeared with Justin Bieber on a late-night show in 2011 when the Canadian singer was just 16 years old. They discussed their close relationship with host Jimmy Kimmel at the time.

Diddy once warned Justin Bieber not to talk about things they did together. Controversial music mogul Diddy appeared with Justin Bieber on a late night show in 2011. “What’s up with you two? Do you work together?” Kimmel asked in a clip circulating online following Diddy’s recent serious legal troubles.

The former Bad Boy Records CEO responded, “No. We became friends in a weird way,” adding, “Justin is like a little brother… He doesn’t hesitate to call me and ask for advice.”

The Bad Boy for Life rapper explained that the music industry is “a strong family,” and many, including himself, want to “wrap around” Justin Bieber to “protect him” because he is “a good person.” 

Diddy went on to praise the Somebody to Love singer : “Besides his talent, he’s one of the best guys I’ve ever met.”

Justin Bieber thanked the Tell Me rapper for his comments, as the audience applauded during this segment. Kimmel joked that perhaps Diddy should buy the young singer a car, like he did for his own son.

“He promised me a Lamborghini, but I don’t have it yet,” the Never Say Never singer chimed in , causing Diddy to look away with an annoyed expression.

“Justin drove the Lamborghini for a day or two,” the Last Night rapper said , apparently referring to a time when they spent 48 hours together, according to a YouTube video Bieber posted.

Diddy once warned Justin Bieber not to talk about the things they did together – Photo 2.

Sean “Diddy” Combs with Justin Bieber and host Kimmel on Jimmy Kimmel Live! in 2011.

“He knows better than to talk about what we did on national television. Not everything is for everyone,” Combs added.

When Diddy and Bieber spent two days together in 2009, the Coming Home singer told Justin they were going to “go crazy.”

Diddy added in a YouTube video: “We can’t reveal where we usually hang out or what we do, but it was definitely a 15-year-old’s dream.”

Amid the ongoing sexual misconduct scandal, another clip of Diddy and Bieber has resurfaced online, showing Bieber visibly uncomfortable with some of Diddy’s comments.

In the video, Diddy says, “Selling tickets is different. You don’t call me to hang out like we used to?”

Bieber is then seen holding a phone, responding: “I tried to contact you through all our partners because you never took my number, do you want to have it?”

However, the singer’s rep recently stated that while Bieber (now 30) “is aware of Diddy’s arrest and all of the allegations,” he “just wants to focus on being a great father and husband.”

Justin Bieber married Hailey Bieber in September 2018. The couple welcomed their first child in August 2024.

Diddy faces charges of sex trafficking, racketeering and transporting prostitutes, and currently faces a minimum sentence of 15 years with a maximum of life in prison.

At a recent press conference, the I Need a Girl singer was accused of sexually abusing 120 people, including 25 minors (some as young as 9 years old at the time of the crimes).

Attorney Tony Buzbee, who hosted the press conference, warned that “a lot of powerful people” will be exposed in connection with Diddy’s misconduct, saying these names will “surprise” the public.

Diddy is awaiting trial behind bars. A court date has not yet been set.