The first W Art Issue cover, from November 2006, was a collaboration between the artist Richard Tuttle and the photographer Mario Sorrenti.
In 2007, Richard Prince took celebrity stock photos and, in a sly commentary on pre–social media celeb culture, scribbled an autograph dedicated to himself on each one of the covers, featuring Jennifer Aniston, Cameron Diaz, Angelina Jolie, Nicole Kidman, Lindsay Lohan, Julia Roberts, Jessica Simpson, and Britney Spears.
Richard Prince’s Lindsay Lohan on W’s November 2007 cover.
Richard Prince’s Jennifer Aniston on W’s November 2007 cover.
Richard Prince’s Britney Spears on W’s November 2007 cover.
Richard Prince’s Nicole Kidman on W’s November 2007 cover.
Richard Prince’s Julia Roberts on W’s November 2007 cover.
Richard Prince’s Jessica Simpson on W’s November 2007 cover.
Richard Prince’s Cameron Diaz on W’s November 2007 cover.
Brad Pitt got behind the camera himself to take intimate portraits of Angelina Jolie and their kids exclusively for W’s Art Issue in 2008.
In this provocative 2009 Art Issue cover, the artist Maurizio Cattelan cast the supermodel Linda Evangelista as both saint and sinner.
Barbara Kruger’s 2010 Art Issue cover says everything we ever needed to know about Kim Kardashian West—then, of course, just Kim Kardashian.
Untitled, 2010, by Barbara Kruger for W’s November 2010 cover, courtesy of Mary Boone Gallery.
For this 2011 Art Issue alternate cover, the artist Francesco Vezzoli reimagines Nicki Minaj as an 18th-century courtesan.
Also in 2011, the first new work that the artist Ai Weiwei made after being released from government custody in China was W’s Art Issue cover, which he made—via Skype—while under house arrest.
In 2013, four artists—George Condo, Rineke Dijkstra, Mickalene Thomas, and Chantal Joffe—reimagined the actress Jessica Chastain for the Art Issue.
Jessica Chastain, W, January 2013.
The artist Yayoi Kusama put George Clooney in her trademark polka dots in December 2013/January 2014.
In 2014, five leading artists used Pharrell Williams as muse, among them Urs Fischer, JR, Rob Pruitt, Mr., and Alex Katz, who painted Pharrell from life during a private sitting.
For the 2015 Art Issue cover, the video artist Bill Viola put Margot Robbie and Jake Gyllenhaal underwater.
Margot Robbie, W, December 2015.
Also in 2015, Yoko Ono revisited her famous “Cut Piece” in an exclusive work for W Art, only this time Ono was doing the cutting.
Meanwhile, five artists reimagined Drake (Katherine Bernhardt, Mark Flood, JIMJOE, KAWS, and Henry Taylor) for the 2015 W Art supplement.
On the 2016 Art Issue cover, Kendall Jenner and Gigi Hadid became “humanoid pets,” thanks to the artists Lizzie Fitch and Ryan Trecartin.
In 2017, the artist Cindy Sherman shot her own kind of self-portrait via phone for the Art Issue.
And on a split 2017 Art Issue cover, Mary J. Blige was photographed by Carrie Mae Weems.
And in November 2018, Cardi B was photographed by the artist Mickalene Thomas for the Art Issue.