In an effort to reach out to younger audiences, Playboy, which turns 57 this year, is increasingly using product placement to promote their brand.

The porn and lifestyle company seems to be targeting video games, as the venerable Bunny appears in "Metal Gear Solid 4." Flipping through the pixelized glossy mag results in the protagonist reducing his stress points. In addition, in the soon-to-be-released third-person shooter "Mafia II," Playboy magazines will be visible in the background to help set the 1950s ambiance.

Then there is Hef and company sliding around in an ad for "Guitar Hero V."

As you've probably noticed, Playboy has also long lent its logo to clothing and other accessories (worn by only the classiest of ladies and gentlemen) and is a titillating presence on reality television. We found some of the least classy and creepiest examples of Playboy product placement and branding. Grab a martini, and enjoy.

"The House Bunny"
The Playboy Mansion and even Hef himself popped up in the 2008 movie "The House Bunny." Yet somewhat inexplicably, Columbia Pictures paid Playboy for the privilege of placing its product in their film. Also inexplicable? A movie about a Playboy Bunny that's rated PG-13.

Pinball machine
Until recently, one could buy a Playboy pinball machine for his or her basement rumpus room. Perhaps the line was discontinued because it suggests the following analogy: pinball is to video games as Playboy is to the digital porn people enjoy in the 21st century.

"Two and a Half Men"
In a 2008 episode of "Two and Half Men," the half-man part of the equation reads aloud an interview that Playboy conducted with Jimmy Kimmel. (Double product placement!) We imagine the show's producers figured a Playboy reference would still be a lot less racy than whatever was going on in Charlie Sheen's life.

Playboy in "Second Life"

Seeing as we are not among the up to 150 million people who have visited the apparently quite complex virtual world known as "Second Life," we don't exactly know what it means that Playboy has an island there. But we like to assume this island has a virtual grotto, and if you visit the virtual grotto you would surely run into a virtual James Caan.

Playboy pencil case
A Playboy pencil case? A retailer in England got in hot water for selling a line of Playboy-branded stationery that included pencil cases and folders. Seeing as very few people of appropriate pornography-watching age would ever purchase a pencil case, WHSmith discontinued the line.