Playboy magazine is opening up shop in Second Life to everyone's surprise ("Playboy isn't in Second Life?"). Although it's unclear what form the Playboy presence will have in the virtual world, as a brand this is a very modern step for Hugh Heffner and his girls. Unlike most of the companies who have set up shop in SL, Playboy seems like it would fit in with community quite seamlessly and they are getting into the virtual business at the perfect time.
Like it or not, being a centerfold or getting an invite to the Playboy Mansion is a very difficult achievement that some people admire. Having Playboy in Second Life is probably the closest most people will get to the brand, and there is a market for men and women (and men acting as women, and vice versa) who want to be a part of it.