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Usher Reveals What Working With Diddy Was Really Like (And Why He Doesn’t Regret the ‘Hardest Days’ of His Life)

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22.04.2026

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Usher Reveals What Working With Diddy Was Really Like (And Why He Doesn’t Regret the ‘Hardest Days’ of His Life)

Usher recalled how his early days with Diddy as a teenager in New York were ‘the hardest days of my life.’

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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........

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