Stephen Colbert, Dec. 19, 2014
Your goal as an editor used to be to turn heads at the newsstand, and during my tenure we gradually came to accept that making a splash in social media mattered just as much, if not more. It’s the rare cover where the subject was having as much fun as the photo and edit crew (and, presumably, the reader). This was at a time when Colbert’s Comedy Central show was closing, and everyone from The New Yorker to Vanity Fair was trying to land him. Only EW gave him a chance to live out a lifelong dream, however, clothing the Tolkien fanatic in bona fide LOTR gear right down to the One Ring as Gandalf, Bilbo, and Legolas. Celebrities have seen it all, but sometimes only EW can take them places even fame fails to reach.
The Reunions Issue, Nov. 14/21, 2014
Everyone has a Bill Murray tale, and this is mine: When a family emergency left Dan Aykroyd unable to make our Toronto Ghostbusters reunion shoot, Murray barricaded himself in a hotel room above the set while Sigourney Weaver, Ernie Hudson, and an entire cast and crew twiddled their thumbs downstairs. He simply wouldn’t go on without Dan. Appeals by Weaver and the cast, Sony Pictures brass, and eventually Ivan Reitman all failed to bring Murray down, and assurances that we’d shoot and include Dan as planned seemed to hold little water. The shoot looked like a massive bust — an expensive one at that. Enter Al Roker, who was there with the Today show as part of our partnership to film the reunions. Roker met with Murray and the cast in a stairwell, calmed everyone down, and coaxed Murray to set. The cover looked great, but it almost never happened.
Gay Teens on TV, Jan. 28, 2011
It captured an important moment and trend in pop culture, and EW was the first to really explore it — an example of EW doing what EW does best. It was also empowering to young LGBT adults and teens in our audience, so it meant a lot to me on a personal level, too.
Stars’ Worst Movies!, Dec. 2, 2011
Well, it seemed like a good idea at the time. We had actually market-tested this cover several times, and it always tested through the roof. But ultimately it tanked, of course. Nobody wants to pay to learn about horrible stuff. However, the story itself is hilarious, one of my favorites. I recommend it to everyone. It just didn’t need to be a cover.
Managing editor, 2002-09
The Dixie Chicks, May 2, 2003 (EW.com poll’s #1 pick!)
At certain times, entertainment can speak to the culture at large, and this cover tapped into the widespread anger over George W. Bush’s disastrous Iraq adventure. After the Dixie Chicks stated their opposition to that war at a concert in Europe, they were vilified by many — including the U.S. ambassador to England — as unpatriotic. The cover image was a ringing endorsement of their right to speak their minds, and in the end, of course, they were proved right: What their president had done was simply tragic.
Million Dollar Baby, Jan. 28, 2005
My least favorite cover is one of Clint Eastwood and Hilary Swank, done for Million Dollar Baby, a movie I loved. It was a failure of imagination on my part. I knew that this would be a difficult pairing for a cover image — as dynamic as they both were in the movie, I didn’t have confidence that we would get a great picture in the short window we had for a photo shoot. It’s an ugly cover that diminishes the actors instead of conveying to our readers just how taut the movie is.
Managing editor, 1990-2002
Jack Nicholson, Jan. 8, 1993
I fought against this cover when it was first proposed because it breaks all the “rules” of cover design. There was no eye contact; it wasn’t a full-face portrait and it was black and white instead of color. But at that time the design and art departments had been fighting with me to do these radical covers that were brilliantly designed but impossible to sell. The person who was particularly vehement about this was the art director, Mark Michaelson. We sat there for quite some time trying to write cover lines, but we couldn’t think of anything I liked. So we all left for the weekend, and I didn’t give it another thought. But Mark apparently sat on a beach and did nothing but think about it. When we came in on Monday, he said, “You Don’t Know Jack,” and it was perfect. I never forgot that because it was emblematic of the dedication and passion so many people brought to the magazine. The unsung hero of EW’s success is Reg Brack (former CEO of Time Inc.) — he had the power to say, “That’s it. We’re shutting you down.” But he believed in us and kept us going during some very desperate times. The fact that we remained alive during those first three years was thanks to Reg.
The Civil War, Oct. 19, 1990
We had a week in October where we had no cover. We were supposed to close on a Tuesday and this was Friday, and we still didn’t have a cover — and there were no prospects. The main thing that was causing a lot of conversation was Ken Burns’ series The Civil War. So I said, “We’re going to do a cover about this PBS show.” So how do we do a cover on the Civil War? I sent [senior writer] Tim Appelo down to Antietam or Gettysburg or somewhere and said, “Find the story.” He looked at me like I was nuts. And he was right to do so. I asked the music department to whip up something about music during the Civil War, and they came back on Monday and said, “We don’t have anything.” At any rate, we did do a cover on Ken Burns’ Civil War in three days, and it was the lowest-selling cover that year. But by God, we did publish that week, so that was a victory.
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Managing editor, 1990
k.d. lang, Feb. 16, 1990
I have reasons to love and hate each of my choices. I have to love issue No. 1 because, of course, it was our first. I’m proud of featuring lang on that cover precisely because she was more talented than known; she set her own path, and so would we. But I’ll confess to cringing when I look at that cover framed on my wall. The design of the entire issue was rightly criticized for trying too hard, being too futzy. We then redesigned the whole magazine in record time, by issue No. 15.
Vietnam War, Feb. 23, 1990
Our second cover is actually my perverse favorite. It featured Vietnam War novelist Tim O’Brien. EW was supposed to be a subscription magazine, which was what allowed me to pick such a high-culture cover. But my business colleagues never told me they’d spent a fortune on supermarket distribution, secretly hoping to launch People Jr. This issue was about as successful as the war it covered.