Inside Usher's Time Living With Sean 'Diddy' Combs

In March 2024, some of Sean "Diddy" Combs' properties were searched by federal agents for an ongoing investigation. Although the exact reason for the search wasn't officially disclosed, a source told NBC that federal authorities had interviewed three people with relations to sexual assault, sex trafficking, and offenses surrounding illegal drugs and firearms. Diddy has found himself as the subject of similar allegations throughout his career but has never been convicted for a serious offense. 

In the aftermath of the 2024 raids, some old videos of celebs discussing their questionable experiences with the producer have resurfaced. Usher, in particular, seems to have had several wild encounters with Diddy since the two lived together for over a year when he was around 13. When the "Yeah" hitmaker appeared on "The Howard Stern Show" in 2016, he shared that record executive L.A. Reid convinced him to briefly live with Diddy for the "Puffy Flavor Camp" experience. 

His time at the producer's house was meant to give him a deeper understanding of the luxurious lifestyle he would enjoy if he had a successful career. While Usher went on to live a lavish life, nothing could've prepared his younger self for the wild times ahead. Speaking to Rolling Stone in 2004, the "My Boo" singer shared that his time at Diddy's home brought a rude awakening about sex, explaining, "There [were] always girls around. You'd open a door and see somebody doing it, or several people in a room having an orgy. You never knew what was going to happen."

Usher couldn't fathom everything he saw at Diddy's home

During his "Howard Stern Show" appearance, Usher further delved into his life as a 13-year-old living under 22-year-old Sean "Diddy" Combs' roof. "It was pretty wild. It was crazy. There were very curious things taking place and I didn't necessarily understand it," the R&B vocalist explained. "I don't know if I could indulge [in that lifestyle] and understand what I was even looking at." When Stern's co-host, Robin Quivers, asked Usher how his parents felt about the wild lifestyle, he admitted they weren't aware of what went down behind the scenes. 

The "DJ Got Us Fallin' In Love" singer gushed that big names like Mary J. Blige and Biggie Smalls frequently stopped by Diddy's home. He revealed that he didn't have a strict bedtime and would sometimes stay up until the early morning hours. All-in-all, it seems like the only normal part of the experience for the teenager was having a daily allowance. When the interviewer asked if he would consider sending his son to "Puffy Flavor Camp," Usher didn't hesitate to answer in the negative.

According to The Things, The "OMG" songster once told an interviewer that when he was 14, he frequently tagged along with Diddy for some of his wild parties because his mentor wanted him to break free from his youth and develop a more edgy persona. The Things also reported that a drunken Combs seemingly revealed that he slept in the same bed as 10-year-old Usher during an interview, and compared their relationship to that of brothers. 

Diddy was accused of grooming Usher

In a March 2024 interview with Art of Dialogue, Sean "Diddy" Combs' former bodyguard, Gene Deal, alleged that the producer groomed Usher. "The Usher part, that's a touchy situation, man," he claimed. "I know and people know that was around in that time that [Diddy] and Usher did have a situation. And that situation led Usher to the hospital." Deal didn't go into much detail as he wanted Usher to have the freedom to tell his story whenever he pleased. However, he claimed that he saw the "U Remind Me" crooner kiss Diddy's then-partner, Kim Porters, immediately after she engaged in sexual activities with the producer.

Overall, Deal seemed frustrated that Usher had said nothing but good things about the man who supposedly groomed him. Neither Usher nor Diddy have publicly commented on these allegations. Meanwhile, people have also got the ick watching a resurfaced video of a 40-year-old Diddy casually hanging out with a 15-year-old Justin Bieber, who was under Usher's mentorship at the time. 

Users took to X, formerly known as Twitter, to express that they couldn't fathom why Diddy would want to spend 48 hours with a child he bore no relations with. In another X video, the record label owner awkwardly asked the young pop star why he didn't want to stay in touch anymore. Bieber seemed uncomfortable as he answered that Diddy had only tried to contact him through his team without ever reaching out to him personally because he didn't have his number and got his phone out to share his contact info.