Caitlyn, Vanity Fair, July 2015
Magazines still have the power to make the world sit up and talk. Vanity Fair‘s latest issue, with Bruce Jenner telling the world to call him Caitlyn, is a prime example. She may have broken the internet even more than her step-daughter, Kim, with that Paper cover.
Angela Lansbury, The Gentlewoman, fall/winter 2012
Angela Lansbury jumped from the newsstands on this powder pink cover for The Gentlewoman, shot by Terry Richardson. The magazine has always offered an alternative vision of women’s magazines, but this issue showed that the mag was willing to represent women of all ages in a way few other titles are.

Alexander McQueen, The Face, April 1998
This exceedingly dark cover of The Face proved to be an eerie premonition. Although it’s quite sad in retrospect, it accurately captured the designer’s fascination with the morbid and gothic.

Kim Kardashian, W Magazine, November 2010
W was one of the first magazines to recognize Kim’s potential to be taken seriously. She fronted the title’s 2010 Art issue, all fresh, plump-faced, with clever coverlines by artist Barbara Kruger.

Are You Mom Enough? Time Magazine, May 2012
This cover created ripples when it was released in the US. The topic at hand was “attachment parenting” and the image of a mother breast-feeding her son beyond the normally accepted age (he’s 3 years old) really made people sit up.

Britney Spears, Rolling Stone, March 1999
This was one of Britney’s earliest covers, published just after the release of …Baby One More Time. Captured in underwear cuddling a Tellytubby, chatting on her phone (with chord!) on pink silk sheets by David LaChapelle, the shot was criticized for being too sexual for the then 17-year-old. “Inside The Heart, Mind & Bedroom of a Teen Dream” reads the coverline.

The Passion of Muhammad Ali, Esquire, April 1968
This 1968 cover came at a time when Ali was stripped of his boxing titles for refusing to fight for the US Armed Forces in the Vietnam War. The art director, George Lois, chose to depict him as a modern day St. Sebastian (an early Christian martyr).

Tupac Shakur, Vibe, April 1995
The coverline shows how much Tupac feared for his life even before he was shot dead in Las Vegas in 96. Vibe reported heavily on the East Vs West Coast beef between him and Biggie, and some argued that they fanned the flames of a fatal hip-hop rivalry.

TLC, Vibe, November 1994
This image is a naughty reference to Lisa Left Eye Lopes’s burning down of her partner Andre Rison’s house. “Burning up the charts, burning down the house” screams the coverline, with the trio partially dressed in firemen’s uniforms. Understandably, it didn’t go down too well with her lover and his family.

Kate Moss, The Face, July 1990
Corinne Day’s portraits of a young Kate Moss prancing round on the beach in a crown of feathers is unbridled joy. It was an early example of the pair’s prolific portfolio of work together.

Helmut Lang, Fantastic Man, Fall/winter 2006
A bare-chested Helmut Lang hugging a cockerel was a stroke of genius from Fantastic Man. Bruce Weber shot Lang far away from the fashion world, showing him on his farm in upstate New York, where he had moved to pursue his art. It’s oozing the offbeat humor that the magazine is known for and was his first big interview since his fashion retirement

Andy Warhol, Esquire, May 1969
Another one from legendary designer George Lois. The issue, hailing “the final decline and total collapse of the American avant-garde” showed Andy Warhol drowning in a can of the Campbell’s soup that he made iconic through his pop art. It was an early case of cut-and-paste and retouching.

Jared Leto, Candy, Summer 2013
The summer before he scooped an Oscar for his role as a trans woman in Dallas Buyer’s Club, he was doing drag on the cover of Candy, Luis Venegas’s “transversal style magazine.” With “There’s no people like show people” written as his eyebrows, it’s a clever hint that Hollywood acting – as RuPaul attests – is all a form of drag.

Kanye West, Rolling Stone, February 2006
Before he christened himself Yeezus, Kanye was visually depicting himself as Christ. Shot by David LaChapelle, the cover saw the rapper sporting his own crown of thorns, complete with the headline “The Passion of Kanye West.” It took 13 hours to shoot and was widely condemned as blasphemous.

Kim Kardashian, Paper Magazine, Winter 2014
Kim did indeed “Break the Internet” with her oiled-up, booty-baring shoot with Jean-Paul Goude, who reworked his own Champagne Incident artwork from the early 80s for the new crown queen of social media.

Beth Ditto, Love Magazine, Spring/summer 2009
The first issue of Love, the first magazine Conde Nast created specifically for one-woman (Editor Katie Grand) saw Beth Ditto bare all for Mert & Marcus. It was Grand setting out her stall for difference, although The Guardian fairly accurately observed that it’s “not evidence of fashion’s new acceptance, but a diversion before emaciated normality returns.”

Prince Fielder, ESPN, 2014
ESPN’s annual Body Issue always causes a stir. Who doesn’t want to check out the sculpted bodies of superhuman athletes? But the mag’s 2014 issue got tongues wagging when it put Prince Fielder on the cover and he commented: “Just because you’re big doesn’t mean you can’t be an athlete. And just because you work out doesn’t mean you’re going to have a 12-pack. I work out to make sure I can do my job to the best of my ability. Other than that, I’m not going up there trying to be a fitness model.”

LeBron James & Gisele, Vogue, April 2008
The cover was at first seen as a triumph, with basketball player LeBron becoming the first African-American man to cover Vogue in the US. But some saw his aggressive stance, face and clutching of Gisele as a brutish, racist King Kong reference.

Janet Jackson, Rolling Stone, September 1993
Janet’s breasts are cupped by former husband René Elizondo Jr’s hands as the headline proclaims “the joy of sex.” The shot by Patrick Demarchelier predates her Super Bowl half time “nipplegate” with Justin Timberlake in 2004.

Rihanna, Lui, 2014
Rihanna’s sweaty sunbather look on the cover of Lui was a throwback to 70s sexiness. Mario Sorrenti shot the singer in bucket hat with braids and nipples out for all to see (fitting for a French magazine, since topless sunbathing has always been the norm there). The shot eventually got the Bad Gal’s Instagram deleted.

Demi Moore, Vanity Fair, August 1991
A preggers Demi (that’s an unborn Scout in there) graced the cover of Vanity Fair. Her “hand bra” and the way she holds her bump made for beautifully composition and a modicum of modesty. Famous art director George Lois called it “an instant culture buster.”

Naomi Sims, LIFE, October 1969
Fashion model Naomi Sims was the unadorned beauty chosen as the face of LIFE‘s “Black Models Take Center Stage” issue. Sadly, more than 45 years later, black models have not attained equality, let alone taken center stage.

Boys will be boys? Girls will be girls! i-D, May/June 1984
Cover star is Sophie Hicks (now known to many as Edie Campbell’s mom) is rocking her typical masculine style with a duct tape cross over her eyes that recalls lesbian pride parades (although they’re usually over the nipples).

The Happy Issue, i-D, December 1987/January 1988
Get Up! Get Happy! i-D encouraged with a winking smiley rave face. It was a time when ecstasy was taking over the UK, so a club kid insider joke from the “trendy fashion magazine.”

The Body Issue, i-D, June 1988
“Acid, casualties and body banter” was the theme of this summer of 88 issue. Discussion of drugs was a central part of the emerging youth culture media market. Oh, and house bhangra was having a moment, too.

The High Spirits Issue, i-D, March 1990
The blurred cover image was a sign of the design confidence of i-D. What other magazine could get away with an out of focus photo on the front? But energy and “high spirits” meant this one worked.

The Paradise Issue, i-D, August 1990
The supermodel as we know it was just being born, and who better to front the “Super Nature” than the flawless Christie Turlington, with crop and basic hoops?

The Screen Issue, i-D, January 1993
Sega’s console superstar, Sonic the Hedgehog, was the magazine’s first animated character cover. He managed a wink and the editorial team took the topic of “game culture” to task. Grunge was also hitting the catwalks, apparently.

The Boys & Girls Issue, i-D, September 1993
The Spice Girls and their “girl power” movement came about a year after i-D announced it on their Naomi cover. And who better to be the first face of the phrase than fierce Ms. Campbell?

The Network Issue, i-D, March 1994
Amber Valletta was the girlish face of the almost lad’s mag cover of i-D’s Network Issue: “funk, punk, junk, spunk” were the shocking headlines. And we were told “Never mind the new punk b*ll*cks.”

Vogue, February 1977
i-D’s Terry Jones and Vogue’s Grace Coddington worked on this jelly cover with photographer Willie Christie. To front the world’s premier women’s glossy with this image was an adventurous thing to do at the time – and still would be today.

L’Officiel Hommes Paris, Will Ferrell
Under the creative direction of André Saraiva, L’Officiel Hommes Paris is adventurous, humorous and always eye-catching. As well as an awesome cover aged French rocker Johnny Hallyday leaning on an electric blue cabriolet, there is this “Will Power!” cover, which sees comedian Will Ferrell rocking Prada as he fist pumps.

Vogue, January 1974
David Bailey’s cover shot of Manolo Blahnik and Anjelica Huston oozes glamour. The champagne sunset moment was a rare, rule-breaking full-length cover at the time of Beatrix Miller and Terry Jones at Vogue.

National Geographic, June 1985
“Afghan Girl” aka Sharbat Gula, was shot by Steve McCurry, who was taking portraits of Afghan refuge in Pakistan from Soviet occupation. Her piercing green eyes matched the background and the garment under her torn, rust colored shawl.

OUT Magazine, May 2007
This cover concept was risky business for OUT, the leading American gay magazine. They took on the idea of “the glass closet”, where celebrities are “out-but-not-really-out,” hiding in plain sight. Models holding masks of actress Jodie Foster and newscaster Anderson Cooper suggested they were gay but just hadn’t come out publicly. It perhaps jolted the pair, as they have both come out since.
