Britney Spears had a night of partying with the controversial Sean ‘Diddy’ Combs in 2007, according to newly resurfaced pictures shared by fans.
The pop star appeared glassy-eyed in the photos, taken just hours before her infamously lackluster performance at the 2007 MTV Video Music Awards.
What Are the Controversial Photos of Britney Spears that Fans Have Recently Discovered?
Photos of Britney Spears partying with Sean ‘Diddy’ Combs in 2007 have resurfaced and quickly became a subject of controversy.
After all, they feature the disgraced music producer, who is currently facing sex-trafficking charges along with other serious federal crimes.
Not to mention, the pictures were taken the night before her performance at the MTV Video Music Awards, a performance that was widely criticized at the time as disastrous.
In the photos, the Toxic singer can be seen smiling and posing with Combs, along with other well-known figures from the 2000s such as 50 Cent and Paris Hilton. In some shots, Spears’ eyes appear glazed.
During Combs’ trial, his ex Cassie Ventura mentioned Spears while recalling her 21st birthday party, which was held at a Las Vegas club.
The event was brought up as she described it as the night she and then-music producer Combs officially began dating.
"Sean was there and he brought [producer] Dallas Austin [and] Britney Spears," she said in court. "I think those were the two people that stand out to me."
They were also invited later that night by 50 Cent to another party at the Hard Rock Hotel & Casino.
What Happened to Britney Spears’ 2007 VMA Performance?
Spears’ appearance at the MTV Video Music Awards, where she performed Gimme More, was supposed to mark her comeback after a three-year break.
However, the pop star was panned at the time for lacking energy. Her poor lip-syncing and weak choreography were also heavily criticized.
In 2023, Spears addressed the incident in her memoir, The Woman in Me.
“There was a problem with my costume and with my hair extensions,” she wrote. “I hadn’t slept the night before. I was dizzy.”
The pop icon also revealed that she ran into her ex, Justin Timberlake, backstage before the performance. Spears dated him from 1999 to 2002 and admitted that seeing him again caught her off guard.
At the time, no one would have thought that being associated with Combs would be a red flag. After all, it wasn’t until recently that he was arrested for alleged illegal activities, following rape and abuse claims filed against him in 2024 by his girlfriend of 11 years, Cassie Ventura.
Although there’s no evidence that Spears was ever involved in Diddy’s so-called “Freak-offs,” secret parties allegedly involving underage sex workers and hard drugs, fans believe that her association with him may have contributed to her career troubles.
Ashlynn Michelle, a Britney Spears supporter, said it all went “downhill” for the Princess of Pop after the party and her VMA appearance. In the months that followed, she was placed under a conservatorship that restricted her freedom.
This was also around the time she famously shaved her head in what was widely reported as a public meltdown, and just months before her divorce from Kevin Federline, with whom she shares two children.
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