My Beautiful Dark Twisted Fantasy (2010)

Singles: "Power," "Runaway," "Monster," "All of the Lights"
Art Direction: Virgil Abloh
Painter: George Condo
Illustrators: M/M Paris 

For My Beautiful Dark Twisted Fantasy, Kanye commissioned legendary artist George Condo to create multiple paintings, including the final, widely-recognized cover censored by retailers such as Wal-Mart for its "sexually offensive" imagery. Who better to create a twisted fantasy than someone who is a master in distorting and re-stylizing the subjects in his art?

It could be argued that Kanye is the man being entertained by the winged woman (allegedly representing Amber Rose) on the front cover of the album, but that was never explicitly confirmed or stated by 'Ye or his label. Various covers were created for the album (which Condo detailed for New York Magazine), including the single cover for "Power" (which is still Kanye's Twitter avatar), but the one that successfully translated to the overall album was also the most controversial. Kanye also commissioned esteemed design duo, M/M Paris, to create the hand-drawn, ornamented frames around Condo's paintings.

Works by Condo were also used for Kanye's merchandise.