In what is one of many instances in 2025 that might have people questioning if certain videos and images are “real” (as in, not AI-generated), Britney Spears, Kim Kardashian and Khloé Kardashian each posted “content” to their Instagram accounts pertaining to their hangout session at the Kardashian abode in Calabasas. Also present was Spears’ latest manager, Cade Hudson, who is something of a “2020s edition” of Sam Lutfi in that he’s constantly seen “squiring” her around and is clearly involved in her life in an overly personal way. This being a pattern of Spears’ and her management selection that seems difficult for her to shake. As is her, let’s say, unique ability to forgive and forget. For God or whoever knows that none of the fans of the Britney Army have forgotten about the Kardashians’ business ties to Lou M. Taylor (via Tri Star Sports and Entertainment Group), the shady figure (for there seems to be no other kind in Spears’ life) who helped Jamie Spears push the conservatorship through in 2008. For both parties stood to gain an ample and continuous payday from claiming “ownership” over Spears’ “person.” Even if her personhood was essentially eradicated as a result of this turn of events.
In 2007, the tumultuous year leading up to Spears’ conservatorship, the Kardashian family was coming up the ranks, landing a reality show called Keeping Up with the Kardashians on E!, thanks to Kim’s long-standing efforts to stick her head up various celebrities’ asses (sometimes, that was more literal than figurative—*cough cough* Ray J). Most especially Paris Hilton’s. It was being the latter’s closet organizer/personal assistant during the early to mid-aughts that launched her into the spotlight, being filmed and featured during certain scenes of The Simple Life and photographed with Paris if she happened to be around when the paparazzi was stalking the hotel heiress-turned-reality star. Indeed, it’s no secret at all that Kim stole, er, learned everything she knows from Hilton. Including, apparently, that Spears is still the girl you want to be seen with.
As Hilton knew well in 2006, taking Spears under her party girl wing when her marriage to Kevin Federline dissolved. In point of fact, the announcement of their separation happened in early November 2006, which is why, by late November, Paris and Britney were the drunken belles of Hollywood nightlife. And the night of November 26th going into November 27th was no exception. Exiting from the Beverly Hills Hotel together, the pair were soon joined by Lindsay Lohan (on a related note, thanks to Paris, Kim Kardashian would eventually become Lohan’s stylist), who jumped into Hilton’s now immortal 2006 Mercedes-Benz SLR McLaren against Hilton’s will. This detail revealed in 2021, when Hilton was only too happy to dish to Andy Cohen, “[She] totally party-crashed. We were all at the Beverly Hills Hotel at the bungalows during an after-party and then Britney and I wanted to leave to go home. Then [Lindsay] started, like, chasing us and then squeezed in the car. And it was literally a two-seater SLR—you know, the sports car. She just, like, squeezed in and I didn’t want to humiliate her in front of all the paparazzi and be like, ‘Get out of my car,’ so I was like, ‘Whatever.’” That shrugging it off, “whatever” stance led to one of the most indelible images of the decade. Far more indelible than the lo-fi, “unvarnished” bullshit that Spears and the Kardashians posted of their hangout session.
While the Kardashians posted photos to their stories—as though Spears isn’t “good enough” for the grid—Britney opted for posting a video to her account that features her kissing both Kardashian sisters on the cheek (in a mise-en-scène and maneuver that has her playing the Madonna role from the 2003 VMAs) as she says, “Oh we’re just chillin’.” “In our geriatric bed,” Khloé adds off-camera. So yes, already, it’s apparent that Spears has come a long way from her partying days of ‘06. As has Kim, once famously photographed chugging a giant Grey Goose bottle through a straw. Now they’re in their cush environs and “cozy” era. But perhaps Spears has gotten so cozy as to forget she herself recently said she probably has brain damage. Which, in truth, would explain why she would deign to engage with these women, of whom she wrote, “Such a warm, beautiful, kind family… Thank you for allowing me to play with your kids and dinner!!! It was an honor to spend time with you guys!!” And therein lies the real potential allure for Spears: that she could have access to children (constantly seeking to regain the motherly time she lost with her own kids) and a family so ostensibly “unified.” A family that would never turn on each other (because it would be too financially disadvantageous to do so—as Lou Taylor also knows).
Spears’ craving for connection and affection of any seemingly genuine variety has once again gotten the better of her. For she ought to know that the Kardashians are the least genuine people in Hollywood, remaining perennially thirsting to be seen with the “right people.” People that will make them look like they have clout. Especially since Kim lost so much credibility when Kanye West’s own took a major nosedive. To that point, the comparison frequently made between Britney and Kanye pertains to the fact that, while Ye has done and said far more outrageous things than Spears, it was Spears who got placed into a conservatorship as Ye continues to run amok. The double standard for men and women being obvious, for while Ye is still heralded as a musical genius (racist and antisemitic rants or not), Spears’ reputation is forever blemished.
Yet Kim apparently needed to watch Framing Britney Spears (a documentary Spears herself abhorred) in order to fully grasp that, commenting at the time, “So I finally watched the Britney Spears documentary this week and it made me feel a lot of empathy for her. The way the media played a big role in her life the way it did can be very traumatizing and it can really break even the strongest person.” First of all, did it really take that documentary to feel empathy for her, considering Kim was lurking as a hanger-on in the shadows in real time when the height of Spears’ paparazzi stalking was going on? And secondly, it clearly did break the strongest person in that Spears’ last shred of resolve to not be desperate enough to hang out with such ilk has been entirely worn down. As it also was during the 2004-2007 period that signaled her downfall (starting with aligning herself with K-Fed).
While this isn’t the first time Spears has been photographed with Kim (the two also got snapped together in 2012 for an event called, of all things, Clive Davis and the Recording Academy’s Pre-Grammy Gala and Salute to Industry Icons Honoring Richard Branson), it is the first time it’s been done in such a casual “we’re besties” kind of way. And it’s not giving “vitality” and “iconic” vibes like that quintessential image of another hangout session from November of 2006. And yes, evidently, Spears likes to have eyebrow-raising hangouts during the month of November.
