9. Marge Simpson, November 2009 – 225,000 copies sold
According to Moe Szyslak, Springfield bartender and local weirdo, “The first time I heard that Marge was going to be on the cover of Playboy, I was upset. I mean, when she found those naked pictures I took of her, she got all up in my face! Of course, she didn’t know I was taking them, but that’s all politics.”
For this issue, Playboy intended to reach out and touch (figuratively, not literally) people in their 20s by including Marge Simpson in the issue. Throwing back to the October 1971 edition where the first black centerfold, Darine Stern, posed for the camera, Playboy’s plan worked like a charm, resulting in 225,000 copies sold. Cue Mr. Burns: Excellent.