Photo: MAC Cosmetics

From Hello Kitty and Wonder Woman to RuPaul and Rodarte, MAC collaborations have pretty much run the gamut from one side of the weird/kooky/cool pop culture spectrum to the other. Just last week, the cosmetics company announced that Nicki Minaj and Ricky Martin (interestingly enough) would represent the brand in their 2012 Viva Glam campaign. The kitsch factor runs high with MAC, and seems to underlie almost every project they take on (the Disney Venomous Villians collection?). And that sense of humor definitely shows through in its newest collaboration with off-kilter-but-awesome American photographer Cindy Sherman, whose daring, conceptual self-portraits question and challenge the way women are portrayed -- and often stereotyped -- in society.

We've rounded up just a few of Sherman's many iconic photographs. And click below to see a slideshow from the photographer's MAC campaign, along with the company's other quirky collabs from the past.

And if you think Sherman's looks are wild, take a peek at these colorful nails.