What: Mattel's 1993 release of an updated Ken doll, with surprising results:

Why: This month's hoax touting an oddly-endowed inflatable Wolverine reminded me of the greatest of all shockingly bad brand extensions. In 1993, Mattel surveyed five-year-old girls about whether Ken and Barbie should be splitsville. Girls supported keeping Ken as Barbie's boy-toy, but they wanted him to look cooler. So Mattel released Earring Magic Ken, which did indeed look cooler. Gone were the preppie pullovers; now Ken was rockin' a lavender leatherette vest with mesh sleeves. He had highlights in his plastic hair and "real clip-on earrings" to boldly display his new sensibilities. Around his neck was the pièce de résistance, a large silver ring on a chain. Of course (and I will say this as gently as I can), another group of people stereotyped for wearing lavender and leather in the mid-1990s also were known for sporting the occasional rings around their necks, but they were used in a different activity. And so the doll became known as "Cock Ring Magic Ken," to the shock and amazement of backpedaling Mattel executives. Not lost in the kerfuffle was the fact that Ken lacked certain essentials to use the bangle for the purpose many thought was intended.

Impact: Dubbed "Queer Ken" by the Stranger's openly gay scribe Dan Savage, Earring Magic Ken soon became the best-selling Ken doll in history. Gay men and kitsch fans across America snatched them off Toys R Us shelves. But Mattel couldn't handle the heat, and recalled the doll from the stores. It's now a sizzling hot collectible. Perhaps confused over their relationship, Ken and Barbie did indeed go their separate ways in 2004, though earlier this year she took him back. It's not clear how their sex life is, but if their creator had any influence, it's certainly not dull.

Personal Connection: While at Hasbro, Mattel's strongest competitor, I was often in brand meetings where all manner of irony-free ridiculousness was proposed. When troubled by brand incompetence, I would use the phrase "Earring Magic Ken" as a neutron bomb. Whatever dumb idea was being championed quickly died on the table. It was the equivalent of shouting "Hitler" in a crowded internet thread. (Of course, I wasn't invited to every brand meeting, so I didn't have the chance to use that argument on this.)

Other Contenders: gunmaker Smith & Wesson hires a chairman who did 15 years in the clink for armed robbery; McDonald's says "When the U.S. wins, you win!" at the Soviet-boycotted 1984 Summer Olympics, then nearly bankrupts itself when the U.S. wins every medal in sight; Harley-Davidson thinks that you want to smell like a biker; Hasbro decides the new Risk is not for women; Facebook sets itself on fire (currently tracking at 16-1 against).