Hasbro is intent on making Monopoly feel new again. Over the last few years, the company has produced everything from Ms. Monopoly, a Girlboss-ified take on predatory capitalism, to the deeply stupid parody of Monopoly: Socialism and the predictably shitty pandering provided by Monopoly For Millennials. Somehow, despite its willingness to commit to seemingly any concept that comes up in meetings, Hasbro has yet to land upon the always reliable idea of simply taking regular old Monopoly and giving it a gritty reboot.
Enter Sinister Monopoly, a show created by an artist whose work does what Hasbro is probably too chickenshit to do itself.
Spotted by Jack Wagner on Twitter, the above clip shows the twisted world of Sinister Monopoly, an art project from someone who calls themselves Sinister Monopoly that’s here presented by YouTuber Ryan Leone. Each canvas is a variation on the same, striking theme: Monopoly’s Rich Uncle Pennybags/Mr. Monopoly engaging in criminal activities so nefarious that he’s transformed into an edgy alter ego called ... Sinister Monopoly. The mustachioed hooligan fires guns, signs contracts while the devil looks on, and runs around with bags of money and weed.
“Over here, this is El Chapo brokering a coke deal with Sinister Monopoly,” Leone says of a piece that shows, true to his word, a cartoon El Chapo shaking hands with Sinister Monopoly in front of the (wait for the twist here) Coca-Cola logo. In case you thought the show was too limited in scope, Leone also shows us work inspired by other interests, like stripper vampires and a painting of a woman’s butt, wrists handcuffed behind her back. (He explains that the painting was made “during the time that the movie 50 Shades Of Grey came out. So this painting, the concept is ‘50 Shades Of Anime.’ Down the side right here, this is Japanese, and it says ‘Sinister’.”)
Sinister Monopoly’s Instagram is filled with extreme works, presented with an opening biography that reads: “Most artwork was done in FEDERAL PRISON while I served an 11 year sentence for CONSPIRACY TO DISTRIBUTE MARIJUANA.” Scroll through the page to discover the Monopoly Man depicted in all kinds of ways you’ve never seen him before. If you fall in love with any piece in particular, just head on over to the show’s sales page to purchase one of these to hang in your living room, perhaps between your framed Reservoir Dogs and Beavis And Butthead “Tommy Pullmyfinger” posters.
Maybe you want to let visitors know what you’re really about by proudly displaying the painting where Sinister Monopoly is getting head from a woman in a bikini while smoking weed? Just $7,500 and that dream can turn into reality.
Console yourself instead with this fantastic runner-up, which shows our man Sinister Monopoly tied up in a straight jacket and thrown away by a society that could never hope to understand him. At $2,500, this is a goddamned steal.
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