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Usher and Diddy’s relationship may never be viewed the same again, however, there was a time, when the popular singer-songwriter lamented his decision to overlook an opportunity to form a group with the music mogul, Jay-Z and the renowned musician Pharrell Williams.

Usher at ServiceNation Summit, New York City

During his appearance on Shannon Sharpe’sClub Shay Shay, theSuperstarsinger described it as one of the biggest regrets of his career while revealing how the discussions surrounding the idea ultimately failed to materialize.

Usher Was Almost in a Mega Music Group With Jay-Z, Diddy And Pharrell Williams

Earlier this year,Usherjoined Shannon Sharpe on his show to share an insight into Super Bowl Halftime Show performance, his life, and some of the biggest regrets of his career in the industry.

When asked about a collaboration that he initially passed on and later regretted his decision, the singer revealed that once he was supposed to be in a group withJay-Z, Sean ‘Diddy‘ Combs, and Pharrell Williams.

Usher on Club Shay Shay

“Pretty wild. It was crazy”: Usher Didn’t Deny If Women Approached to Have S*x With Him When He Was Living With Diddy as a 14-Year Old

“Jay-Z, Pharrell, Diddy, and me were supposed to be a group,”he said before further explaining that though he didn’t explicitly turn down the offer, he didn’t clearly say yes to the opportunity either. Reflecting on the missed prospect, he shared onClub Shay Shay,

Yeah, that’s crazy. I didn’t say ‘No.’ I didn’t say ‘Yeah.’ I think that we just got caught up. I think we all got caught up in the moment.

“Pretty wild. It was crazy”: Usher Didn’t Deny If Women Approached to Have S*x With Him When He Was Living With Diddy as a 14-Year Old

“We was talking about it and having secret meetings about it,”he said before adding,“We were talking about music and how we gon’ flip it and the business of it.”

The singer further shared that despite all the discussions and foresight into the collaboration with Diddy,whom he had praised occasionally,it never came to fruition, as he described it as one of the biggest regrets of his career.

Sean ‘Diddy’ Combs in Draft Day

Usher Reflected on Some of the Biggest Regrets of His Career

Further into their conversation, Usher shared thatthe collaboration with Diddyand Jay-Z was one of the things that he truly wished he had pursued.“And somehow, man, we just got distracted and it never happened,”he said as he expressed his regret, saying,“That’s the one I actually wish would have happened.”

He then revealed he was considered to star in the 2006 adaptation of the hit Broadway musicalDreamgirls. He reflected on receiving the offer for the movie, saying,

Jennifer Hudson, Beyoncé Knowles and Anika Noni Rose in Dreamgirls

There is a movie or something that I was supposed to be a part of… David Geffen reached out to me to be in Dreamgirls… yeah man it just didn’t happen.

Directed by Bill Condon,Dreamgirlsfeatured an ensemble cast of Jamie Foxx,Beyoncé, Eddie Murphy, and Jennifer Hudson. Usher wasreportedlyin talks for the role of C.C. White in the movie, which ultimately went to Keith Robinson.

P Diddy Slept With Usher and Justin Bieber- Suge Knight Comes Back With More Serious Claims About Diddy’s Alleged “Boyfriend”

Dreamgirlswas a critical and commercial success, earning $155 million at thebox officeand won two out of eightOscar nominationsat the 79th Academy Awards, including Best Supporting Actress for Jennifer Hudson and Best Sound Mixing.

Dreamgirlsis available to watch on Paramount+​.

Laxmi Rajput

Senior Writer

Articles Published :3448

Laxmi Rajput is a Senior Writer at FandomWire, with over 3,300 articles published covering film, TV, and pop culture. With a degree in Broadcast Journalism and over three years of experience in content writing, she pivoted to entertainment journalism because let’s be honest, superheroes, sitcoms, and Netflix binges are way more fun. Laxmi frequently covers Marvel, Harry Potter, Star Wars, and popular TV shows, offering both fan-first enthusiasm and thoughtful analysis. Her work often dives into Marvel theories, revisits the genius of The Big Bang Theory, or unpacks the Netflix phenomenon of Stranger Things.

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DiddyJay-ZPharrell WilliamsUsher