The relationship between Usher and Diddy is well-documented at this point. During Usher’s teenage years, he was sent to the Bad Boy Mogul’s house to get his debut, self-titled album ready.
Over time, he credited Diddy as one of his mentors and part of the reason he made it as far as he did in the industry. However, despite all of this, the Confessions star admitted that those were “the hardest days of my life.”
In a 2004 profile with Rolling Stone, Usher recalled feeling extremely lonely and isolated during his time in New York. But one revelation was obvious: “Sex is so hot in the industry, man.” He admitted that it was Diddy who introduced him to “a totally different set of s**t” in his teenage days.
Diddy was the executive producer on Usher’s self-titled debut album in 1994
“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,” he told the publication.
Usher said he did his fair share of experimenting but never actually had sex until he was 19 years old. “Strange, but I never busted a nut before then,” he added. “I’d just do it until I could tell the girl was feeling good, and then I’d stop.”
In spite of the uneasy age discrepancy and the tough times, the singer today doesn’t “have anything negative to say about Sean Combs.” In a March 2026 conversation with Forbes, he emphasized that we shouldn’t take away from the legacy Diddy has built to this point.
Usher Reveals Diddy Introduced Him to Sex in His Teens
“I’m not saying that every man is perfect,” Usher insisted. “I’m not saying that all of us don’t have flaws, but I can’t with any sense of humanity not recognize the valuable contributions that this man made for us as Black entrepreneurs, for us as people who transition culture and ideas into something that’s tangible. SO many people benefited from what he created. And I acknowledge that. That’s why I see him as legacy.”
Then, Usher added that Diddy was responsible for monetizing culture and creating something “colorless.” Moreover, Sean Combs aided him in understanding the music business from the onset of his career.
“There are trials and tribulations that come with the pressures of success and power,” he said. “But what we choose to do with it is what I hope that you see with me and hopefully other people that I’m involved with, right?”
The post Usher Reveals What Working With Diddy Was Really Like (And Why He Doesn’t Regret the ‘Hardest Days’ of His Life) appeared first on VICE.
