2023
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 COVER OF THE YEAR
New York
“The Pleasures of Outdoor Dining,” October 24–November 6, 2022
David Haskell, Editor in Chief
Thomas Alberty, Designer
Jody Quon, Photography Editor
Beth Sacca, Photographer
View 2023 Winners and Finalists Gallery
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2022
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 COVER OF THE YEAR
New York
"The Lunacy of Text-Based Therapy," March 29-April 11, 2021
David Haskell, Editor in Chief
Pablo Rochat, Illustrator
View 2022 Winners and Finalists Gallery
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2021
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COVER OF THE YEAR
The New Yorker
"Say Their Names," June 22
David Remnick, Editor
Kadir Nelson, Illustrator
View 2021 Winners and Finalists Gallery
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2020
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COVER OF THE YEAR
New York
“Impeachment Season Begins,” October 14–27
David Haskell, Editor in Chief
Tom Alberty, Designer
Joe Darrow, Illustrator
View 2020 Winners and Finalists Gallery
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2019
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COVER OF THE YEAR
TIME
"Her Lasting Impact," October 15
D.W. Pine, Designer
John Mavroudis, Illustrator
View 2019 Winners and Finalists Gallery
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2018
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COVER OF THE YEAR
The New Yorker
"Blowhard," August 28
David Plunkert, Illustrator
View 2018 Winners and Finalists Gallery
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2017
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COVER OF THE YEAR
TIME
"Total Meltdown," October 24
D.W. Pine, Creative Director
Edel Rodriguez, Illustrator
View 2017 Winners and Finalists Gallery
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2016
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COVER OF THE YEAR
Vanity Fair
"Call Me Caitlyn," July
Chris Dixon, Designer
Annie Leibovitz, Photographer
View 2016 Winners and Finalists Gallery
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2015
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WINNER
The New Yorker
"Broken Arch," December 8
By Bob Staake
View 2015 Winners and Finalists Gallery
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2014
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 COVER OF THE YEAR
Boston
"We Will Finish the Race," May
Photographed by Mitch Feinberg
View the 2014 Winners and Finalists Gallery
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2013
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 COVER OF THE YEAR
New York
"The City and the Storm," November 12
View the 2013 Winners and Finalist Gallery
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2012
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 COVER OF THE YEAR
New York
"Is She Just Too Old for This?," October 3
Photographs by Danny Kim
Photo-Illustration by Darrow
View the 2012 Winners and Finalists Gallery
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2010
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 COVER OF THE YEAR
Harper's BAZAAR
December (Subscriber Edition)
View the 2010 Winners and Finalists Gallery
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2009
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 COVER OF THE YEAR
Rolling Stone
July 10-24
View the 2009 Winners and Finalists Gallery
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2008
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 COVER OF THE YEAR
New York
March 24
View the 2008 Winners and Finalists Gallery
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2007
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 COVER OF THE YEAR
The New Yorker
September 11
View the 2007 Winners and Finalists Gallery
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2006
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COVER OF THE YEAR 
The New Yorker
"Flood in the Oval Office," September 19
View the 2006 Winners and Finalists Gallery
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