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The Gossip Reading Club: Issue Sixteen – Tom Ford's Hollywood Issue of Vanity Fair (with Emma Fraser)

Tom Ford takes over Vanity Fair's Hollywood Issue with sleaze, glamour, and nudity.


Kayleigh Donaldson

Nov 04 2021

24 mins read


Welcome to a new edition of the Gossip Reading Club! This week, we're looking into one of the real modern institutions of celebrity coverage, and the issue that stands as perhaps its most iconic. And infamous.

Vanity Fair. “Tom Ford’s New Hollywood.” March 2006.

Image via Vanity Fair // YouTube.

Launched in 1995, Vanity Fair’s inaugural Hollywood Issue was described as a celebration of sorts for the year the movies turned 100 (although this isn't entirely accurate to the history of cinema in the United States, since the world's first commercial motion picture exhibition was given in New York City in 1984.) The first issue came with the title "The Power and the Glamour" and was accompanied by photography by Vanity Fair favourites like Annie Leibovitz and Herb Ritts. There are no detailed paragraphs of context or reporting to accompany this piece. It's almost exclusively glossy images with a few snappy descriptive paragraphs accompanying them. Even then, they mostly just detailed present and upcoming projects by the subject and a fun label. For instance, Julia Roberts was The Ingenue, while Sophia Loren was The Goddess. Image came first, the creation of icons rather than anything deeper than aesthetic. The actors provided the glamour and the power was covered by images such as a two-page spread of major producers, including Dino De Laurentiis, Jerry Bruckheimer, and Danny DeVito. The final person featured is Nancy Reagan, the "hometown girl." 

Over the years, the Hollywood Issue became more high-concept. The 2007 issue took the form of a lavish noir-inspired film, complete with a plot that allowed the stars to dress up and play characters. In 2008, they paid homage to the films of Alfred Hitchcock. This year's theme was... uh, something sort of surreal and colourful? But no Hollywood Issue sticks more in the mind than 2006 when guest editor duties were handed over to the fashion designer Tom Ford. This issue certainly made an impression on me, and I knew that I wanted to do a special of the newsletter on it, but I couldn’t do it alone. I’m very excited to be collaborating with a friend and colleague today, one of the best writers on style in pop culture! 

Emma Fraser is a freelance culture writer with a focus on TV, movies, and costume design. She has contributed to Elle, Vulture, The Cut, Little White Lies, and more. She joins me today to dive into Tom Ford’s Hollywood Issue in all its strange, stylistically jarring, and areola-obsessed glory. 

(NSFW Warning!)

We both love this image (via Vanity Fair.)

Emma: Funnily enough, the 2006 Hollywood Issue is the first time I bought a copy of Vanity Fair and I haven’t missed a copy of this annual tradition since. I would consider myself a magazine aficionado that began in childhood with football magazines like Shoot and has never really abated. Recently, I have fallen into a habit of buying vintage print copies from eBay and this includes pre-2006 Hollywood Issues (I picked up the inaugural edition for a very reasonable price). I have a vague recollection of wanting to buy this particular 2006 cover because of the furor surrounding it as it would have been at a time when I tuned into E! News habitually — something I haven’t done in a long time with the internet so freely at hand. I am pretty sure I subscribed soon after, which was likely a result of an ad for a discounted price and the free gift deal sweetener. I canceled this probably around 2011 but always made sure to get the Hollywood Issue and then re-signed up as a print subscriber when Radhika Jones took over as EIC in 2017. 

Kayleigh: Looking back, I cannot remember if the 2006 issue was the first Vanity Fair I ever bought. I’m about 70% sure it was, but, like you, I certainly remember all of the hubbub around its cover. 2005/6 was the first time I, a long-time lover of film, began to be truly intrigued by the industry side of the equation. That was the first Oscar race I became obsessed with and followed for every possible detail to predict the final winners and you can imagine how burned I, a 15-year-old Brokeback Mountain stan, was when Crash beat it to Best Picture. I’m still mad. The Vanity Fair Hollywood Issue seemed, from my outsider perspective, to be a crucial part of that glitzy awards season rollout. Everyone certainly talked about it as such, and this issue got a lot of attention. 

It was one of those things that E! News, This Morning (the British version of the Today Show but way weirder), and the like really obsessed over. I distinctly recall how scandalous the image of Tom Ford posing (fully clothed) with naked Keira Knightley and Scarlett Johansson was considered. At the very least, there was a tawdriness to it all that went against that image of glamour and irreplaceable Hollywood shine that the cover was intended to convey. Gawker described Johansson's cleavage as "The Rack" while Knightley was called "pasty". Rebecca Traister of Salon derisively called the issue "a giant package of artificial cheese", with "topless bodies found in [a] brainless magazine." It didn’t help Vanity Fair’s case when it was revealed that Rachel McAdams was supposed to join Johansson and Knightley on the cover but backed out after feeling uncomfortable with the naked setup. 

Emma: In terms of how long I had been invested in the Oscars, the first ceremony I stayed up to watch was when I was at university and the year of the Lord of the Rings sweep. Before that, I took a cursory interest and read magazines like Empire, Total Film, Premiere, and Hot Dog (remember that?). Like you, the Crash year is seared into my brain and a defining Academy Awards. This issue did have that inside air when coupled with how the Vanity Fair party factors into the night of the show. The Old Hollywood deep dives also give it authority and while Tom Ford was establishing the “new”, it is impossible to separate this issue from the past.

 Some of the descriptions of their bodies are mind-boggling and sadly not surprising (considering both their skin tones are the same shade it seems perplexing that only Knightley is ‘pasty”). In the Los Angeles Times, Robin Abcarin calls Johansson “baby chubby” against Knightley’s “ultra-thin” silhouette, which is as exhausting as some of the descriptions you have already mentioned. The value judgment here pits both women against the other and it is a frustrating introduction to an article that does a good job of breaking down the lack of originality in the so-called new vision. Abcarin writes, “For a magazine celebrating Hollywood, the combination of the dressed male and the naked heterosexual woman is merely a metaphor for how things are, have always been and will probably always be.” And this brings us to the portfolio and the famous photographer Ford tasked with bringing this brief to life.    

Scarlett Johansson behind the scenes of that cover photoshoot (via Vanity Fair.)

Kayleigh: Ford’s issue is dedicated to “New Hollywood”, although the definition given for that term isn’t quite so specific:

"This year is just such a year of change. Not all of the new faces in New Hollywood are in fact new. Some are not even young, but all of a sudden the world has shifted, or they have finally found their voice, and they are stars. Perhaps they have even been stars for a while, but just when we thought they could burn no brighter they have turned into supernovas. Perhaps they finally landed the role that suits them. Perhaps some are just fluff, and we know deep down that we will tire of them soon, but, for the moment, we have a crush and can't get enough. Or perhaps it is just the pendulum of mass taste swinging in the direction of their particular charms. Whatever it is, it catapults them to a new level in the sky and into our collective heaven."

2005 certainly did have some major cinematic milestones. Ang Lee's Brokeback Mountain was a major cultural milestone, Felicity Huffman received an Oscar nomination for playing a trans woman in Transamerica (which is certainly problematic but was viewed as a big step forward for LGBTQ+ Hollywood cinema at the time), and films with major geopolitical themes like Munich, The Constant Gardener, and Good Night and Good Luck performed well. Of course, the box office was dominated mostly by franchise fare such as Harry Potter, Star Wars, and Narnia. Brangelina made their debut with Mr. and Mrs. Smith, Peter Jackson rebooted King Kong, and Christopher Nolan reintroduced Batman to the world with Christian Bale. 

So, Ford's vague objective has some grounding: This was a year where up and comers found their breakthrough roles or became true legends. Others exhibited the kind of potential that fizzled out quickly (Vanity Fair's Hollywood Issues are a fascinating document of the bright young things who never got past their own hype.) But it is certainly easy to look at this array of stars at the time and believe that they were going to be our generation's golden figures. The job of the issue, then, is to reinforce that. The Hollywood Issue is primarily defined by its images but words are there. Each photograph is accompanied by a paragraph of text that sounds like a mixture of publicist-mandated details, gossip column fizz, and gossip tidbits overheard at a magnificent party. Everyone gets a fun moniker too: Dakota Fanning is The Starling; Sienna Miller is The It Girl; Bob and Harvey Weinstwin (yikes) are The Warriors. 

Emma: Looking back at old Hollywood Issues is often a game of images that aged badly or those stars who have since faded. With the former, there are the obvious subjects who are now persona non grata and a slew of figures who have since gone on to Oscar and career triumphs. The loss of both Heath Ledger and Philip Seymour Hoffman still cuts deep and it is impossible not to feel a twinge of sadness when landing on their pages. Calling Gyllenhaal and Ledger the “New Heartthrobs” seems off considering Donnie Darko came out in 2001 and 10 Things I Hate About You was nearly a decade old by this point. The duo that should’ve got this heartthrob title is Max Minghella and Jamie Bell, and while they are not photographed to appear together (if you look closely you will see that Ledger and Gyllenhaal were on different coasts), the pairing of their images is purposeful (and they have subsequently worked together). 

One title that makes more sense is Peter Sarsgaard as the Chameleon and the shot of him in a suit bound in bondage ropes is one of the more effective. Again, the male subjects look in control even when they are tied up. Reese in 1960s-adjacent attire plays into the imagery of Walk the Line (that she would win Best Actress for) and the doll is a nod to motherhood. This is before she entered the producer waters and at this time she was very much branded as a young mom and wife — this issue is a time capsule of star power and how this shifts over time. Sure there are fewer legacy images (think the Hustons lined up together) but it doesn’t feel all that different from previous years (nudity aside). 

That year

Kayleigh: Some images are extremely creepy, most notably the one of Topher Grace where he seems to be posing as a member of the Rat Pack who’s a serial killer of women on the side. Photographed by Terry Richardson, an accused sexual predator infamous in the industry long before he was exposed by the press, Grace has a malicious smirk on his face that I suppose is meant to read as charming. The presence of an identity-less woman held up by her feet like a cow’s carcass in a slaughterhouse doesn’t exactly have the same effect. It’s an unsettling image, to be sure, but it’s also hugely at odds with the image Vanity Fair wants to create of Grace. You can't describe a guy as being "the new Tom Hanks-Jack Lemmon-James Stewart" then show him posing like a man who has literal skeletons in his walk-in closet! The "unassuming quality" the magazine talks about isn't here. It's no surprise that Richardson also photographed the image of Jason Schwartzman in this issue, which features yet another faceless nude woman as decoration. 

Looking at these poor disembodied women, I, like Rebecca Traister in Salon, ended up thinking about Killing Us Softly, Jean Kilbourne's lecture, which later became a cycle of documentary films, focused on gender stereotypes and misogyny in advertising. Even today, it's horribly common to see products sold using women's nude and disconnected bodies: a pair of well-manicured hands holding a perfume, legs with no body showing off shoes, the nude form reduced to furniture. The products here are the men themselves, their images moulded into a kind of skeezy masculinity, not uber-muscled but nonetheless macho, seeming impossible for women to resist. Well, that's the theory. As with all Richardson images, the ambiance is more crime scene chic. Even if you put aside the many years of allegations leveled against Richardson (some of which were well-known at the time of this issue's publication), he remains a terrible fit for this issue's ethos. 

Emma: The disconnect between the moniker Grace has been given and that shot suggests that Ford has never seen a James Stewart, Jack Lemmon, or Tom Hanks movie. I jest of course but there really is no connection beyond the tuxedo (and that isn’t even a defining attribute of those performers per se). The bare-legged woman in the Grace image is Ford’s personal assistant Whiney Bromberg who stepped in “after the original model bagged it at the last minute.” This information is shared openly in Ford’s introduction and while models must drop out all the time it is a coincidence or conspiracy situation that several participants dropped out. The women as disembodied objects do give a lurid aesthetic that captures what was considered edgy at the time but is distinctly creepy thanks to the man behind the camera and the accusations. It is also serving “Blurred Lines” vibes, which wouldn’t debut until seven years later and yet has a similar sensibility — both also feel like the kind of thing that if you voiced an objection to you would get called a prude or a killjoy. Additionally, Ford’s second time behind the camera on Nocturnal Animals also has a motif of crime scene chic. 

Even the photographs where the women are the subject have a layer of vulnerability that is absent in the shots of the men. There is an interesting conversation in Ford’s explainer of the issue that discusses Eric Bana’s discomfort with the original concept of him wearing a Speedo stretched out across the water and. The alternative set-up included a robe as a compromise that Ford notes still captures the Hollywood fantasy — it is unfortunate that a white hotel bathrobe is now associated with another person who features in this portfolio. What is noticeable is the carefully curated anecdotes that are shared and the ones he withholds. The order of the images also tells a wider story including opening with a 12-year-old Dakota Fanning (photographed by VF mainstay Annie Leibowitz) before shifting into the sexually charged imagery. Hollywood has never been shy in featuring child stars among adults but this inclusion is a little queasy — even if her pose is far from provocative. But at least she isn’t on the page opposite a comically large (on purpose breast) and the order doesn’t always make a lot of sense. 

"The man

Kayleigh: It’s a strange mixture of sleaze, camp, and an attempt at Hollywood glamour that blends contemporary with classic. That leads to some very weird choices that are, to put it bluntly, very boob-forward. Sienna Miller poses in nothing but pants and heels. The headless model in the Schwartzman image reveals both breasts and butt. Joy Bryant poses totally naked. Most of it feels salacious, to put it kindly, and not especially alluring, at least to me. It works far better when the images lean into the ludicrousness of it all. This might be best exemplified by The Breast Friends, where Pamela Anderson and Mamie Van Doren recreate the iconic shady image of Sophia Loren glancing suspiciously at Jayne Mansfield's cleavage. It's a funny image, one that lets two women oft-defined by the male gaze be in on the joke. 

Although it does seem somewhat pointed when contrasted with an image on the next page of The Enhancer, Dr. Garth Fisher, who the magazine describes as a plastic surgeon known for "his light touch around the face and his subtle boob jobs." He's photographed on the golf course next to a giant breast. The elephant in the room, so to speak. The accompanying paragraph for Fisher, who was one of the original doctors on the TV equivalent of evil known as Extreme Makeover, is very weird: 

"When they are young and pretty, they leave their hometowns in droves and they go to L.A. They land a part here, a part there, and a Screen Actors Guild card comes in the mail—or perhaps they find themselves in the airy offices of CAA or Paramount. They delight in the sunshine, the beaches, the rides in convertibles. Years go by in a pleasant California haze, but human flesh, no matter how moisturized, proves no match for time and gravity, and the human form, no matter how toothsome, doesn't always live up to L.A.'s inflated expectations. Body parts that once stood at attention begin to droop, and so comes the day when our gorgeous L.A. creature no longer elicits those stares while strolling the sidewalks of Sunset Boulevard. This is where Dr. Garth Fisher, the original star of ABC's Extreme Makeover series, steps in. A plastic surgeon praised in the pages of Town & Country and Los Angeles magazines, he's known for his light touch around the face and his subtle boob jobs. Those entering his Beverly Hills office often find that sometimes just a little Botox zap between the eyebrows—Ah! Wondrous elixir of youth!—is all they need to make it through that next audition or power brunch."

I suppose there is something to be said for this candid acknowledgment of how beauty and ageing actually works in Hollywood, something that, to this day, remains coded in non-confirmations and insistence that it’s all down to good genes and cold cream. Still, this description of the “young and pretty” being confronted with the seeming terror of time kind of bums me out. It wisely avoids gendering these future patients of cosmetic procedures but it still feels somewhat directed towards women, at least within the context of this issue. It’s a puncture in the illusion, certainly, but to what end? After all, the image of this wonderful doctor is overshadowed by a giant tit. 

Genuinely wasn

Emma: Michelle Yeoh gets the unfortunate placement of being on the page opposite the very free nipple, which means it is impossible to look at her pose of strength without becoming distracted. In the case of nodding to the artifice of Hollywood and the additional treatments and surgeries, I agree that it is being candid but told once again through this sleaze lens. Ford wants to sell the fantasy of Tinseltown and this is just as much part of that package. 

The shift in tone from humorous to self-serious does make it feel like the issue is having an identity crisis of sorts, which could also describe the latter period of Graydon Carter’s reign. It would be over a decade before he would leave his role as EIC, and the Hollywood Issues that followed ticked the usual boxes with later issues rightly getting called out for lack of diversity. The Ford cover got spoofed in the Comedy’s New Legends touting issue in 2009 with Paul Rudd playing the Tom Ford role and Seth Rogen, Jonah Hill, and Jason Segel playing Knightley, Johannson, and the absent McAdams. The body stockings are of course a wink at the so-called hilarity of it all, and once again points to the different standards male comics and actresses undertake. What do you make of this choice to poke fun at the Ford issue only three years later?      

Kayleigh: It seems like a case of Vanity Fair trying to have its cake and eat it to me, especially since they didn’t even let the guys go nude. It fits in nicely with Hollywood Issues of the past, where men tend to be tuxedo-clad and women are either dressed to the nines or showing some skin (the now infamous first ever Hollywood Issue featured actresses like Jennifer Jason Leigh and Nicole Kidman posing in some of the most unflattering lingerie of the decade.) Vanity Fair tends to have a pretty solid sense of humour about itself but that joke cover/pseudo apology felt like kind of a copout to me. Maybe if we had an issue where all the Hollywood Chrises posed like that, sans body stockings, things would even out.

The Hollywood Issue remains a curious kind of relic, one that, like basically everything else in awards season, we probably invest in more than is really necessary. You don’t have to be in the issue to be an Oscar favourite, just as you don’t have to have appeared in a Hollywood Reporter roundtable. It doesn’t hurt to play the game, of course, but said game has changed since 2006. The Hollywood Issues have gotten noticeably slimmer and less ambitious, a reflection of the ever-dire state of magazine publishing. The photoshoots tend to be less varied and eclectic, either sticking to a theme or going the default classic glamour look. It’s a stark contrast not just from the Ford issue but those that preceded it. Check out the issues of the ‘90s and they’re kind of bonkers, full of wildly contrasting images, a vast variety of stars, and an industry-wide scope that is absent in the actor-focused ones of today. These Hollywood Issues used to contain group shoots of beloved writers or images of agents and publicists and critics like Pauline Kael. Even Nancy Reagan was included one year (eh.) I do miss that aspect of the Hollywood Issue, that understanding that what makes the town tick goes well beyond the above-the-title stars. They cared about Old Hollywood and that just isn’t as present in more recent issues. Granted, we’re losing that generation to the sands of time but there’s still so much untapped potential I would have loved to see. 

I had this image on my wall when I was a teenager!

Emma: Earlier this year I ended up buying some old issues of VF from eBay (including several Hollywood issues from the ‘90s and early ‘00s) and the noticeable shift aside from the high advertising budget is the streamlining of the photoshoots and even the array of Old Hollywood stories. There are still deep dives into the past but the contemporary stories that sit alongside it reveal this desire to keep up with the fast-paced machine of the present. The internet and how we consume famous people have changed a lot since the Tom Ford issue and part of me wonders if social media (and particularly Instagram) has made it even more superficial. There has always been a mix of breakout stars and the old guard, but it feels even more geared toward those who are looking to get their face out there or have a comeback. I miss the inclusion of those behind-the-scenes figures and it is amazing that someone like Pauline Kael was featured.  

It has always been a superficial overview of the year in stars — the blurbs have at least got slightly longer — but the chaos of those early years is missing. The other factor is that it is all about going viral now so the year when Benedict Cumberbatch played table tennis against Oscar Isaac (while wearing tuxedos) was always going to linger in my mind. Obviously, the Hollywood PR machine has existed as long as the studios so none of this PR spin is new but the access around this time of year is so specific to the awards game. Or at least looking like you could be a future contender. As you mentioned, the THR roundtable issue is as much a fixture and for the truly weird photoshoot, you need to look no further than W magazine. Vanity Fair used to be the one to watch and now there is competition (even if print media is no longer king). As for the future, I think EIC Radhika Jones has breathed new life into the magazine and the online awards content is some of the best there is, however, the Hollywood Issue is stuck between how it was and how the magazine now is. Looking back at the issues under Jones’s tenure and the 25th-anniversary issue in 2019 is the most effective and if this is going to remain a mainstay (and I hope it does) then diversity in cover stars is also key. Additionally, in terms of Old Hollywood stories it is clear from podcasts like You Must Remember This and The Plot Thickens that there are still plenty of untold tales to be uncovered.

Kayleigh: The 2022 issue certainly has potential for grandeur and variety if we’re going by the array of actors and industry figures in the spotlight for awards season: the Nightmare Alley cast, everyone and their accents in House of Gucci, Kristen Stewart as Princess Diana, Jessica Chastain in Tammy Faye disco camp, and so many musicals! I don’t expect Vanity Fair to go back to its ‘90s excess for obvious reasons (remember that whole pandemic thing?) but I hope they retain that sense of fizzy fun. Awards season is kind of ridiculous anyway so why not go all out? We may be in the age of “relatability” with celebrities but I think we still crave some of that glitz that only Hollywood can indulge us with.

"The New Direction", an ensemble of women directors, from the 1996 issue (via Vanity Fair.)

Emma can be found on Twitter and Instagram at @frazbelina. You can check out her work in many locations but I highly recommend her Luke Kirby profile and conversation with the costume designer of Impeachment: American Crime Story. She’s also doing weekly Succession reviews that I highly recommend you read. My big thanks to Emma for joining me in this issue. You’re always a blast to work with and it’s cool being your friend and colleague!

You can find my work on as well as sites like SYFY, IGN, Uproxx, Slashfilm,, and many other places. This past fortnight, I talked about sexy Santa Claus romances, I revisited True Blood, and hoped that maybe we could just not make movies out of wildly sexist books written by giant racists. Over on Crooked Marquee, I wrote about one of my favourite vampire films, Guillermo del Toro's Cronos. On SlashFilm I got in the spooky mood with The Innocents and preached the joys of Rocky Horror's sequel, Shock Treatment! I also made my debut on Mubi Notebook talking about the erotic dramas of one of my favourite directors, Philip Kaufman.

The Gossip Reading Club is free to read and shall remain so. However, if you would like to donate a couple of dollars towards its upkeep, you can do so on my Ko-Fi page. It takes a lot of work to put these together and now I have to pay for the newsletter service (and write this stuff on a laptop that has crashed twice during the posting of this dang issue.) Thanks so much to everyone who has been so generous in recent weeks. I seriously appreciate it!

I'm really eager to hear from you, dear gossip readers, about topics you'd like to see covered in this newsletter. Is there a famous story or scandal or particular profile you'd like to see me look into? I am open to any and all ideas as long as the article is easily accessible. Enjoy your weekend!

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