Usher was just 13-years-old when he burst onto the scene and was given a taste of a rapper's lifestyle through living without his parents at Diddy's New York pad.
Bizarrely, Usher was sent packing from his hometown of Dallas, Texas, and was sent to live with Diddy, real name Sean Combs - who was nine years older than him.
The 46-year-old has labeled what he saw there when he was just a schoolboy as 'wild', and now during a conversation on the Baby, This is Keke Palmer podcast, fans believe his answer to an 'uncomfortable' question was him reliving those years.
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Host Keke Palmer asked: "How old were you when you had your first kiss? And who was it?"
Usher replied: "How old was I when I had my first kiss? Erm, that I actually intended to have? You know, I had, you know... there was a couple of, you know..."
Immediately Palmer understood the potential trauma that Usher was reliving and changed the subject.
Taking to Twitter, a fan posted the snippet of the podcast episode to applaud the host as well as flag the hardships that Usher faced during his teen years.
"This clip is….hm. Very sad and telling. But Keke is very sharp and social/emotionally intelligent. I see why she has gone so far in this industry. Very good interview," they posted.
Before later adding: "I really hope Usher writes a book one day. His story is very fascinating. I know he doesn’t do many interviews but it was so interesting."
The 34-second clip has been seen more than five million times, garnering hundreds of comments.
One user wrote: "I love how she pivoted. With the way he answered, it’s possible that the question could have triggered him a bit or at the very least made him uncomfortable. It takes emotional intelligence to notice that and act on it."
While a second added: "It's honestly horrifying that as old as he is it is still very painful to recall those memories. Some things just never go away."
It comes as Usher said that he wouldn't send his own kids to live with Combs like he did at the age of just 13.
Speaking to Howard Stern back in 2016, he was asked if his parents were okay with what he was experiencing. In response, the 45-year-old admitted that they 'didn't know nothing about this s**t'.
"You're a dad now, would you ever send your kid to Puffy Flava Camp?" Stern went on to ask.
"Hell no," Usher, a father-of-four, replied.
While Usher explained he witnessed 'very curious things' happen during his time living there, there is no suggestion that anything inappropriate happened towards Usher because of Combs, who remains in jail as he awaits trial - due to take place on May 5.
Combs was indicted by a grand jury following his arrest at the Park Hyatt hotel in Manhattan back in September.
Combs has since been charged with racketeering and sex trafficking by force, fraud or coercion, charges he's continued to deny. A 14-page federal indictment accuses the rapper of organizing events known as 'freak offs'.
UNILAD has contacted Usher's representatives for comment.
Joe Yates