Britney Spears was seen partying all night with Sean “Diddy” Combs before her disastrous performance at the 2007 MTV Music Video Awards. The “Toxic” songstress was captured in resurfaced photos smiling alongside the Bad Boys Records founder at Jet nightclub in Las Vegas on Sept. 7, 2007. Later that same night, Spears joined Combs, Paris Hilton, and 50 Cent at the Hard Rock Hotel & Casino for another party hosted by the “In da Club” rapper. The bash continued into the early hours of Sept. 8, 2007, leaving everyone wondering what time Spears finally called it a night.
The photos of the 43-year-old “Womanizer” hitmaker partying with the 55-year-old Combs were brought to light after Casandra “Cassie” Ventura mentioned Spears during Combs’ ongoing sex-trafficking trial. Ventura, now 38, testified that her relationship with Combs “sort of” began in September 2007 while celebrating her 21st birthday in Las Vegas. The night in question was recently highlighted during Ventura’s testimony at Combs’ trial, where she recalled the presence of Spears and music producer Dallas Austin at the event.
Despite the wild night of partying, Spears infamously took the stage at the MTV VMAs on Sept. 9, 2007, to perform her song “Gimme More.” The performance was highly anticipated as her comeback, but the pop icon faced widespread criticism for her lackluster choreography and poor lip-syncing. Throughout the night, Spears was photographed with Combs, adding fuel to the fire of media speculation and scrutiny. In her 2023 memoir, “The Woman in Me,” Spears detailed the chaos that ensued before her ill-fated performance, including costume and hair extension issues, lack of sleep, and overall dizziness.
Encountering her ex-boyfriend Justin Timberlake backstage only added to Spears’ pre-show nerves. The singer, who dated Timberlake from 1999 to 2002, admitted in her memoir that seeing him again after a long time was unsettling. The public eye was already fixated on Spears due to her divorce from Kevin Federline and the highly-publicized head-shaving incident that occurred months prior. All these factors contributed to the mounting pressure and scrutiny that Spears faced leading up to her MTV VMA performance. The night of partying with Combs and other celebrities was just the beginning of a tumultuous chapter in the pop star’s life.
