Jennifer Aniston: A New Vanity Fair
My last essay at The Squawk two weeks ago was about the 20th anniversary of Jennifer Aniston’s Vanity Fair cover story for the September 2005 issue which has become mythological for its place in gossip history. I have a thing about milestones, particularly gossip milestones, and I’m pretty happy with how I timed the piece, just before the issue would have been released two decades ago, but I’m even happier now because I swear, I wasn’t tipped off that Jen would be covering the September 2025 issue of Vanity Fair, but I did have a feeling.
And look… it happened.
One of the points I was trying to make in my essay at The Squawk is that Jen’s interview back in 2005 for the magazine has become legend, not only because it was her first extensive interview since breaking up with Brad Pitt but because it represents a time in gossip when there was gossip in the magazine interviews. As I wrote in my newsletter, even her friends were out here spilling tea on Brad and Angelina and emotional affairs and enchantments and cheating and… it would never happen again. Jennifer Aniston was never as candid as she was in that interview in 2005. Which she pretty much confirms in this interview in 2025.
“I haven’t looked at that article in forever. I just remember the experience of doing it—which was kind of jarring. It was also such a vulnerable time. But yeah, that was one for the memoirs.”
Because, amazingly, it read like a memoir, and this is what makes it iconic now since, as we have seen, celebrities do not move like this for magazines anymore. Jennifer Aniston’s 2025 Vanity Fair interview gives almost nothing, it will not be commemorated in another 20 years because there’s nothing to commemorate. I just read it, twice, and there’s not much to take away here where the gossip is concerned. In fact, the only thing worth pull-quoting comes via an assist from… who else but Gwyneth Paltrow. But even there, what starts off as gossip turns into, ugh, wellness. Which, in itself, might be a metaphor for Celebrity in general. As in, these people used to be so fun and dramatic and now they’re just kale.
“Gwyneth Paltrow is another close friend, whom Aniston met decades ago when her Friends costar David Schwimmer was filming The Pallbearer. Their love interests overlapped off-screen as well as on. While discussing the genesis of her and Paltrow’s relationship, Aniston says, “Ironically, I went to her and Brad’s engagement party,” meaning Pitt, the man who proposed to them both. Aniston and Paltrow’s friendship outlasted both women’s Pitt chapters, but I can’t help but ask, do they ever talk about Pitt?
“Oh, of course,” Aniston says, waving her hand and sounding everything like Rachel Green. “How can we not? We’re girls.” But they trade wellness intel more than gossip. “We’re always swapping advice—‘What are you doing for this? What are you doing for that? Do you have a new doctor for that?’”
Jen, of course, is covering Vanity Fair ahead of season four of The Morning Show, premiering in a few weeks on Apple TV+. The profile is a collection of quotes from her friends about how chill and nurturing she is. That in her 50s she’s remodelled her life the way she does her homes: cozy, comfortable, and full of crystals. Seriously, Jen’s VF25 interview ends with her giving advice to the reporter:
“I think you should get some rose quartz”—[for] unconditional love—“and amethyst. And also for this year, the year of the snake—now this is where I start to sound like a crazy person—white jade.” For grounding.
If she’s already out here with the crystals, quartz, and amethyst, how is white jade for the year of the snake pushing over the edge of crazy? The Chinese zodiac and feng shui have been around a lot longer than white women woo woo but you know what happens when the blonde lifestyle influencers leech onto something, right? Suddenly they’ve f-cking discovered it.
Now I need a goddamn crystal to settle my rage. So I’ll direct to you the most insightful content that Jennifer Aniston gave Vanity Fair; it wasn’t during the interview, it was for their rewatch feature as she’s filmed looking back on some of her past projects, including The Breakup, Horrible Bosses, and more. She makes a cheeky comment about the timing of The Breakup which was filmed right after her divorce from Brad Pitt and also talks about some of the creative contributions she made in her movies. For example, the button she pushes in Horrible Bosses to lock Charlie Day in her office while she sexually harasses him was her idea. That movie happed before Matt Lauer was fired and now I’m wondering if she was on the whisper network about his f-cksh-t well in advance of it becoming public.
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