Just two days before her widely criticized 2007 MTV Video Music Awards performance, Britney Spears was seen partying in Las Vegas with music mogul Sean “Diddy” Combs. Recently resurfaced photos capture the pop princess smiling next to the Bad Boy Records founder at Jet nightclub on September 7, 2007 a moment that, in hindsight, paints a telling picture of the chaotic days leading up to her infamous appearance.

The party didn’t stop there. Later that night, Spears joined Diddy, Paris Hilton, and 50 Cent at the Hard Rock Hotel & Casino for another lavish celebration, this time hosted by the "In da Club" rapper. The festivities reportedly continued into the early morning hours of September 8. While it's unclear exactly when Spears left the event, it's evident she wasn't in a restful state before what was meant to be her grand musical comeback.

Cassie’s Testimony Sheds New Light on That Weekend

These images have re-emerged in the wake of testimony from singer Casandra Cassie Ventura, who recently mentioned Spears during Sean Combs’ ongoing sex-trafficking trial. Ventura testified in court on May 15, 2025, that her own relationship with Combs sort of began that same weekend while celebrating her 21st birthday in Vegas. “Sean was there, and he brought Dallas Austin, Britney Spears. I think those were the two people that stand out to me,” she said.

On September 9, 2007, Spears took the stage at the VMAs to perform “Gimme More.” What was supposed to be a triumphant return turned into a disaster. Fans and critics slammed her lethargic dancing and awkward lip-syncing. In her 2023 memoir, 

The Woman in Me, Spears admitted, “Nothing was going right.” She mentioned wardrobe malfunctions, lack of sleep, and even an uncomfortable backstage run-in with ex-boyfriend Justin Timberlake.

At the time, the star was already facing intense media pressure, a custody battle with Kevin Federline, and fallout from her headline-making breakdown months earlier — all of which set the stage for a performance that would live in infamy.