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(CNN) -- When Annie Leibovitz photographed the heavily pregnant actress Demi Moore for her private album, she never intended for that image to be seen by a wider audience.
But the young editor Tina Brown decided to put the picture on the cover of her magazine Vanity Fair. That was 1991.
More than two decades later, that very Vanity Fair cover is one of the most memorable images of our time.
"I didn't expect the storm that it created," Brown, now editor-in-chief of The Daily Beast and Newsweek Global, told CNN. "It was a good risk because we put on an unbelievable amount of sales. It became a kind of iconic picture for women."
The cover was one of a series of bold and sometimes controversial decisions that have cemented Brown as one of the most influential magazine editors of a generation.
The risks Brown has taken -- from adding celebrity culture to highbrow news magazines to ending the print run of Newsweek magazine -- have brought both success and failure throughout her career.
"Unfortunately taking risks comes so easily to me that you can call it reckless at times," said Brown. "I have to hold myself back a little and think 'wait a minute, be careful because you know you can blow it, too.'"
British-born Brown revived the fortunes of two ailing bastions of the newsstand, Vanity Fair, which she began editing aged just 30, and The New Yorker.
In the 15 years Brown edited Vanity Fair, she took its monthly sales from 200,000 to 1.2 million and is credited with saving the magazine with her signature formula of mixing serious news with celebrity culture.
She again worked her magic at The New Yorker, which she edited for six years, increasing circulation by 145% on the newsstand and 28% overall.
In 1998, she left The New Yorker to launch Talk Magazine, which folded after only three years.
Her latest venture is perhaps the most controversial of all. Brown launched news website The Daily Beast -- named after the fictional newspaper in the Evelyn Waugh novel "Scoop" -- in 2008 and merged it with Newsweek in 2010.
While The Daily Beast is gaining a loyal digital readership -- with up to 16 million unique users a month and advertising up 30% year on year -- Brown's Midas touch has yet to work on Newsweek.
Like many weekly print magazines, circulation for Newsweek has slumped -- from three million in 2007 to 1.5 million in 2012. And after 80 years on the newsstand, Brown took the stark decision to make Newsweek an all digital publication, printing its farewell edition on December 31, 2012. Twitter lit up with #LastPrintIssue, which also featured on the last cover of the magazine's final edition.
Although it continues as an online magazine, its owner IAC has now announced it is seeking a buyer for the Newsweek brand.
At the age of 59, Brown is now running an all digital business for the first time in her career, and divides opinion on whether she can adapt her operation to meet the demands of a fickle online media world.
"Great editors have great successes and great failures," says Ken Doctor, digital media analyst and author of Newsonomics, "[Brown] had remarkable success with Vanity Fair and The New Yorker, but Talk was a spectacular failure.
"She is a 'tweener,' connecting Britain and U.S. sensibilities, connecting celebrity and serious news, connecting print and digital. There are not many people who have done that.
"She has ridden with the times in creating The Daily Beast; she is someone who adapts and learns."
Others, however, see Brown as a great magazine editor of her time, and believe she has yet to master the digital media landscape.
"She is a creature of a different age," says Jeff Bercovici, media and technology staff writer at Forbes. "The formula she brought with her is the opposite of what works online. In the digital world, successful sites have started really small and gradually built up with unknown writers. Her line was to hire expensive writers and do something with panache, but that doesn't work online."
Though she has her critics, Brown marks her own success by the fact that people are still talking about her.
"I don't think any editor wants to put out anything that falls into silence," says Brown. "I do tend to have points of view that are sometimes counter to the wind."