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Britney Spears partied all night with Sean ‘Diddy’ Combs before disastrous MTV VMAs 2007 performance

Resurfaced photos show Diddy’s connection to one of the most disastrous nights in Britney’s Spears’ musical career.

Kid Cudi reflects on 'stressful' testimony in Sean 'Diddy' Combs trial

Britney Spears partied all night with Sean “Diddy” Combs before her disastrous performance at the 2007 MTV Music Video Awards.

Resurfaced photos of the songstress show her smiling alongside the Bad Boys Records founder at Jet nightclub in Las Vegas on September 7, 2007.

Later that 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.

L-R: Britney Spears, Sean
L-R: Britney Spears, Sean "Diddy" Combs, Paris Hilton and Dallas Austin party in Las Vegas on September 7, 2007. Picture: Johnny Nunez/WireImage
Diddy’s then-girlfriend Cassie (right) has testified she remembers partying with Britney (left). Picture: Denise Truscello/WireImage for Jet Nightclub
Diddy’s then-girlfriend Cassie (right) has testified she remembers partying with Britney (left). Picture: Denise Truscello/WireImage for Jet Nightclub

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The bash continued into the early morning of September 8, 2007, though it’s unclear what time Spears went home.

The photos of Spears, now 43, partying with Combs, now 55, were unearthed after Casandra “Cassie” Ventura name-dropped Spears during Combs’ ongoing sex-trafficking trial. (The rapper has denied the charges against him.)

Cassie, now 38, testified that her relationship with Combs “sort of” began in September 2007 while celebrating her 21st birthday in Las Vegas.

“Sean was there, and he brought Dallas Austin, Britney Spears. I think those were the two people that stand out to me,” Ventura said in court on May 15.

Clockwise from top left: Britney, Diddy, 50 Cent, Paris Hilton and Dallas Austin party together. Picture: Chris Polk/FilmMagic
Clockwise from top left: Britney, Diddy, 50 Cent, Paris Hilton and Dallas Austin party together. Picture: Chris Polk/FilmMagic
Britney and Diddy party the night before the VMAs. Picture: Jean Baptiste Lacroix/WireImage
Britney and Diddy party the night before the VMAs. Picture: Jean Baptiste Lacroix/WireImage
Britney deletes revealing video amid fan concern

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Spears infamously took the stage at the MTV VMAs on September 9, 2007, to perform her song Gimme More.

The performance was expected to be her comeback, but the pop icon faced widespread criticism for her lacklustre choreography and poor lip-synching.

In her 2023 memoir, The Woman in Me, Spears wrote that “nothing was going right” before she performed.

Britney’s 2007 VMAs performance was universally slammed. Picture: Kevin Winter/Getty
Britney’s 2007 VMAs performance was universally slammed. Picture: Kevin Winter/Getty
The star appeared woozy and uncertain on her feet during the performance. Picture: Kevin Winter/Getty
The star appeared woozy and uncertain on her feet during the performance. Picture: Kevin Winter/Getty

“There was a problem with my costume and with my hair extensions,” she wrote.

“I hadn’t slept the night before. I was dizzy.”

Spears had also bumped into her ex-boyfriend Justin Timberlake — whom she dated from 1999 to 2002 — backstage.

“It had been a while since I’d seen him,” she wrote. “I couldn’t believe I was going to have to go out onstage feeling the way I felt.”

At the time, the singer was also facing intense public scrutiny after divorcing Kevin Federline and infamously shaving her head months earlier.

This story originally appeared on Page Six and is republished here with permission.

Originally published as Britney Spears partied all night with Sean ‘Diddy’ Combs before disastrous MTV VMAs 2007 performance

Original URL: https://www.ntnews.com.au/entertainment/britney-spears-partied-all-night-with-sean-diddy-combs-before-disastrous-mtv-vmas-2007-performance/news-story/1f4f015cd953f6acf04f5a65ef0ca5e8