Usher's longevity in the music industry proves that, at the end of the day, the singer has many more moments to celebrate than he does moments to regret.

However, during a recent interview on the Questlove Supreme podcast, the 38-year-old admitted that one specific circumstance, involving Chris Brown, is something he has come to deeply regret over the years.

During the conversation, he and the esteemed drummer tackle a variety of subjects, including the diving into what he would consider the biggest regret of his career.

"So there’s one thing in my career that I definitely regret, one thing," Usher begins. "And to this day I battle with it which is why I always show support of this artist whenever he asks."

From there, Usher dives into details, explaining how his first introduction to Breezy resulted in a missed opportunity.

"So his manager comes in..." he continues. "They show him to me… I was working on an album at this time, they wanted him to perform on this album. I was like, 'okay cool.' Then I went to my team and they were like 'I don’t think you should work with this artist'... Then he left... Chris Brown."

Luckily, although he regrets not collaborating with Chris Brown earlier in his budding career, the two have blessed the same song several times in the past. Perhaps Usher may be able to recruit the singer for his next project to rectify the situation even further.

Listen to Usher's recent on-air conversation with Questlove in full here.