Last Friday, Eminem released the video for his latest Recovery single, "Space Bound" (which you can watch above), starring retired porn star Sasha Grey. Grey, best known for her award-winning adult film career, has been foraying into more serious acting lately, the kind where she gets to keep your clothes on and, you know, actually act. Since her work in the indie drama The Girlfriend Experience and on HBO's Entourage, along with modeling gigs for American Apparel, Grey has become an unlikely "It" girl within the mainstream.

The beautiful brunette isn't the first porn star to collaborate with Marshall Mathers, though. In fact, Em has built a reputation of casting adult film actresses in jokier videos for blatantly gratuitous bits, which sets Grey's more dramatic role apart. In the bleak "Space Bound" clip, Grey plays Eminem's love interest whom unwittingly fuels his self-willed demise. Which makes her first (former) porn star not cast for her adult film past.

Well, that's just our observation; feel free to draw your own conclusions, while gaining newfound appreciation for Mr. Shady, as we look back upon Em's history of casting porn stars in his videos.