Usher Revealed The Creepiest Things He Saw Living With Diddy For A Year

Sean “Diddy” Combs is currently at the center of a scandal involving several allegations, including sex trafficking. His homes were raided and Diddy was arrested. This led the public to speculate about whether the allegations could be true. Much of Diddy’s past began coming to light, including an interview where Usher made shocking revelations.

In a clip from The Howard Stern Show, Usher described his experience living at Diddy’s New York City home when he was just 13-years-old. Based on what Usher told the radio host, the experience didn’t sound appropriate for a young pre-teen.

Fans also began connecting the dots to Justin Bieber, who once considered Usher a mentor. Justin has since unfollowed Usher on Instagram and many are wondering if the Diddy connection is the reason. Justin himself even spent some time with Diddy as a young teen, which has led to even more speculation.

Usher Opened Up About His Time Living With Diddy At Just 13-Years-Old

Following the raids on Sean “Diddy” Combs’ homes in 2024, an interview with Usher began resurfacing online. The interview was from an appearance the singer made on The Howard Stern Show in 2016. During the conversation, Usher spoke to the radio host about his experience living with Diddy when he was 13-years-old.

Howard asked Usher if it was L.A. Reid’s idea for him to live with Diddy. Usher responded by saying there were “very curious things taking place” while he lived at Diddy’s New York City residence. Based on what he told Howard, it was clear he was exposed to things that a 13-year-old shouldn’t have been exposed to.

“I got a chance to see some things,” Usher said. “I went there to see the lifestyle — and I saw it. I don’t know if I could indulge and understand what I was even looking at. It was pretty wild.”

He also told Howard that there were other famous artists who constantly hung around Diddy’s home. These big names included Biggie Smalls, Lil’ Kim, Craig Mack, Faith Evans and Mary J. Blige. Howard asked Usher if he was actually staying up until 4 a.m. partying with Diddy and his crew. Usher told Howard that he “could” and “actually stayed up longer than them.” He said the whole experience was “pretty crazy.” When Howard asked Usher if he would ever let his kids go to “Puffy camp,” the singer said firmly, “H*** no.”

This wasn’t the only time Usher spoke about his experiences at Diddy’s “Flavor Camp.” In February 2024, he shared some more details about his experience when talking to People.

“I can remember Outkast making their first records and being able to hear Rico [Wade] work on these songs, literally sleeping in this man’s living room, being in the dungeon, just kind of being around and just trying to figure out who’s who,” Usher told the outlet.

According to Usher, the experience wasn’t just about the music, it was also about “the energy” and the various artists he met “were teaching me and showing me how to act and how to present myself.” Usher also remembered the first time he met Diddy. Usher revealed that he first invited him to come to New York so he could start working on music.

“I got a tutor, went to New York City, and he began to show me the ropes,” he remembered. “Some of the most valuable lessons I could ever learn as an entrepreneur were picked up when I spent that time in New York with him, this unwavering desire to create and make certain that your creative ideas executed.”

Usher continued, “I saw him in the real time working it out, him building something from nothing, him understanding how culture and collaboration could build careers. Being able to see that, that’s what I got.” Usher even revealed that he was “privy to” watching The Notorious B.I.G. make his 1994 album “Ready to Die.” The singer said he was “watching it in real time,” but he didn’t fully grasp “the value of what I was getting in that time.”

Usher also spoke to Rolling Stone in 2004, where he opened up about how Diddy introduced him to “a totally different set of s*** — sex, specifically.” The interview saw Usher going into more detail about what he allegedly saw at Diddy’s house than he did with Howard.

“Sex is so hot in the industry, man,” Usher revealed. “There was 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.”

People Began Questioning Diddy’s Relationship With Justin Bieber After The Allegations

In March 2024, federal agents raided Diddy’s homes in Los Angeles and Miami, according to Homeland Security Investigations per People. These raids happened following two lawsuits in which Diddy was accused of sex trafficking.

“Earlier today, Homeland Security Investigations (HSI) New York executed law enforcement actions as part of an ongoing investigation, with assistance from HSI Los Angeles, HSI Miami, and our local law enforcement partners. We will provide further information as it becomes available,” a statement by a Homeland Security Investigations representative read.

According to TMZ, federal police arrived at Diddy’s L.A. property, with helicopters flying above. Meanwhile, FOX11 showed a video of Diddy’s sons Justin Combs and Christian ‘King’ Combs in handcuffs outside their home in Beverly Hills. Diddy’s lawyer condemned the raids in a statement. “There was a gross overuse of military-level force as search warrants were executed at Mr. Combs’ residences,” attorney Aaron Dyer said. “There is no excuse for the excessive show of force and hostility exhibited by authorities or the way his children and employees were treated.”

“This unprecedented ambush — paired with an advanced, coordinated media presence — leads to a premature rush to judgment of Mr. Combs and is nothing more than a witch hunt based on meritless accusations made in civil lawsuits,” the attorney added. In conclusion, the statement read, “There has been no finding of criminal or civil liability with any of these allegations. Mr. Combs is innocent and will continue to fight every single day to clear his name.”

After the allegations blew up, past clips of Diddy hanging out with Justin Bieber resurfaced on social media. The two were seen talking about spending a “crazy” 48 hours together in one of the clips. This particular clip comes from a video that was posted to Justin’s official YouTube channel.

Diddy looked at the camera and said, “He’s having 48 hours with Diddy, where we hanging out and what we’re doing we can’t really disclose. But it’s definitely a 15-year-old’s dream. I have been given custody of him. He’s signed to Usher when he did his first album. I don’t really have legal guardianship of him, but for the next 48 hours he’s with me. And we’re gonna go buck fool crazy.”

There was another resurfaced clip which show Diddy giving Justin a bottle on his birthday. Justin then kneels down to drink from the bottle while a woman shouts, “Happy Birthday Justin!” There’s even an old episode of Keeping Up With The Kardashians from 2014, where Justin is mentioned. In the clip, Khloé mentions Justin was in attendance during her experience at one of Diddy’s “naked parties.”

“I got on a plane at 5.30am. Well this party…I think half the people there were butt naked,” she is heard telling her sister Kourtney. She then said she was hanging out with “a bunch of friends” and listed off “Diddy. Quincy. Justin Bieber…”

Justin Bieber Unfollowed Usher, His Former Mentor, In The Wake Of The Diddy Allegations

After the allegations against Diddy made headline news, Justin Bieber unfollowed Usher, his former mentor, on Instagram. Usher was one of many that Justin would unfollow on the platform. These names included his former manager, Scooter Braun, and team members Allison Kaye, Ryan Good, Poo Bear, and Kenny Hamilton. Many wondered why Justin unfollowed Usher and some believe it had to do with the Diddy connection.

However, this wouldn’t be the first time Justin has snubbed Usher. In February 2024, Usher spoke with The Breakfast Club radio show where he revealed he asked Justin to appear at his Super Bowl halftime show. However, Justin turned him down. Despite this, Usher said he didn’t hold it against the singer.

“I honor and recognize that my brother, you know, he — I think that it might’ve been the fact that he’s just wanting to tell a different story right now, and I understand that,” Usher said. “But we did have a brief conversation, and we’re gonna do something else in the future. No love lost or anything like that.”

Usher said that performing at the Super Bowl comes with a “lot of pressure” and he “reached out to everybody” to make an appearance. “Justin wasn’t the only person that I actually spoke to about doing the Super Bowl, but the moment was maybe for later,” he revealed. “He’s gonna play the Super Bowl. I’ll go ahead and give you that — in the future. I profess that over his life. It’s time, because he has a career that deserves it. But it just didn’t happen, but that doesn’t mean it’s not going to.”

Lil Jon, who joined Usher on stage during the halftime show, told TMZ Live that Justin “wasn’t really ready” to perform. “We wanted to put Justin in the show, so we had the idea of doing a version of the show with Justin in it,” he said. “But I think Justin just wasn’t really ready. That’s a lot of rehearsal, a lot of responsibility, a lot of time and a lot of eyeballs. I don’t know if he was ready to do all of that, you know?”

Justin watched the game with wife Hailey in a suite at Allegiant Stadium. Lil Jon said that this was a sign of Justin supporting Usher even though he wasn’t performing with him. “I mean, he definitely was there supporting Ush. They’re really good friends, and he definitely was supporting him regardless.”