Vanity Fair’s annual Hollywood issue is an institution. Its success is due to a simple premise: gathering together the most glamorous stars of awards season, dressing them up all nice and forcing them to stand around sullenly in a series of agonising CIA stress positions. That sounds like fun, doesn’t it? That’ll reverse the death-spiral of the publishing industry!
With this year’s Hollywood issue hitting the shelves this week, it only seems right to take a look back and count down, the 10 most awkward Vanity Fair covers in history.
10 – 1995
“Guys, Vanity Fair here. Listen, we want to start an annual event where we find the most attractive women working today and put them on the cover together. One quick thing: they all need to be wearing their nighties. What’s that? Sarah Jessica Parker doesn’t own a nightie? Well, we’ll just put her in a bra and a skirt. Linda Fiorentino doesn’t own a bra? This is a nightmare. How about we just get everyone to pull a really disappointed face. Would that work?”
9 – 1997
You’ll remember 1997 as the year Hollywood ran out of ThermaCare Heatwraps. As a direct result, it became impossible for Vanity Fair to source a raft of actors who weren’t completely incapacitated by lumbar pain. Just look: Charlize Theron has quietly snuck a hand behind her back for support, Jada Pinkett is attempting to stretch it out and Claire Danes is in huge amounts of distress. And then there’s Renée Zellweger, clearly in a state of excruciating discomfort having just lugged a piano all the way up a flight of stairs for a bet.
8 – 2003
While the only thing asked of these covers’ female participants is to exude a louche sense of sexual availability, male actors use them as an opportunity to express their true personalities. So in 2003, we got Tom Hanks looking grandly understated, Ewan McGregor looking like he’s just had a big dinner, Tom Cruise looking like all he wants to do is make a Kenny Loggins biopic, Matt Damon looking like all he wants to do is make a Scrappy Doo biopic and Jack Nicholson seeming far too invested in the imported porn VHS that’s almost definitely playing right behind the camera.
7 – 2016 (pictured at top)
Halfway through the afternoon, there’s a knock at the door. “Diane Keaton, what are you doing here?” asks Annie Leibovitz. “I’m here for the audition,” replies Keaton.
“What audition?”
“For Homepride Fred: The Movie. I’m up for the lead. I think it could be my greatest role.”
“Sorry Diane, this is the Vanity Fair cov-”
“But I’ve prepared a monologue! It’s about cheese and ham potato bakes.”
“Fine, stand in the corner. But don’t bother Mirren. She’s in a terrible mood.”
6 – 1996
The year that Vanity Fair, in a fit of deluded egotism, attempted to create a new boyband. There’s DiCaprio, the heart-throb. There’s Roth, the bit of rough. There’s Del Toro, the enigma. There’s Schaech, the hunk. There’s Rappaport, the anonymous one who stands at the back not doing anything. There’s McConaughey, the unnecessarily jaunty one. There’s Ulrich, the disapproving Victorian policeman.
Their first single did not chart.
5 – 2005
How best to distract everyone from a mortifying “IT’S FAHRENHEIT 90210!” cover splash? Simple: force the year’s biggest stars into a zero-sum Leibovitz-off, each tasked with pulling their most stereotypical Annie Leibovitz pose. Although Uma Thurman, Kate Winslet and Scarlett Johansson all do fine jobs – going for bored opulence, furious judgement and distracted constipation respectively – the winner was ultimately judged to be Claire Danes, who died.
4 – 1999
It’s fair to say that 1999 was not a golden year for Hollywood. Things were so fraught, in fact, that Vanity Fair was reduced to putting minor stars like Monica Potter, Vinessa Shaw and Barry Pepper on the cover of its most prestigious issue. Perhaps this explains the decision to just make everyone wear whatever they could grab during a 45-second trolley-dash round the Gap store.
3 – 2011
“Fancy grabbing a quick pint after work?”
“No, not tonight.”
“Why not?”
“I was in there at lunch and it was full of dickheads all standing in a row. James Franco won’t stop sitting on the bar, even though there are chairs.”
“That doesn’t sound too bad…”
“Jesse Eisenberg seems convinced he’s James Bond, and I’m pretty sure that Andrew Garfield is defecating.”
“I still think we should go.”
“And there’s a bloody tiger or something there.”
“Come on, just one drink. Who’s working the bar?”
“Robert Duvall.”
“OK, let’s leave it.”
2 – 2000
Sorry to have to break this to you, but the police are currently coming to your house to seize your computer after you used it to briefly look at this image featuring Selma Blair looking like a four-year-old at a paddling pool party and both of Chris Klein’s nipples at once. It’s not ideal, I realise, but the law is the law.
1 – 2006
The year: 2006. The theme: what Jeremy Piven sees whenever he closes his eyes. Fun fact: this cover is now being used in Las Vegas to advertise an undersubscribed hypnotism stageshow called Zargo The Mysterious Traumatises Your Subconscious.
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