Did you know Charlie Sheen is an inventor and holds a genuine U.S. patent? It's true. It's not a sex toy (although it sure looks like one). But if his $100 million lawsuit against Warner Bros. and Two and a Half Men producer Chuck Lorre doesn't work out, he can always fall back on the crazy business schemes he hatched in the 1990s. Here's a survey.

Sheen has already launched a line of "Duh? Winning!" t-shirts to capitalize on his ongoing physical and emotional implosion. But even before he began spouting electric 9/11-denying poetry from his fingers, Sheen was something of a reluctant entrepreneur.

A search through patent and trademark databases shows that Sheen—through a now-defunct company called Masheen, Inc.—laid the groundwork for a host of business schemes that for some strange reason never seem to have gotten very far. One of them was a line of anti-drug paraphernalia. Really.

Here's what we found:

"Chapstick Dispensing Apparatus"

Sheen's patent. Click to view the document (PDF).

In 1999, Sheen and Roger D. Thomason jointly filed to patent a design for a chapstick dispenser with a "slidably, pivotably, or hingeably attached" cap, thereby solving the vexing problem of lost and wayward chapstick caps. This thing should have been huge! Except for one thing: It didn't help you do cocaine.

Anyway, the patent was granted in 2001, so he's always got that baby in his back pocket.

"Drugs Are Loser Friendly"

Click to view the trademark application

In 1998, Masheen Inc. trademarked the phrase "drugs are loser friendly" for use on "printed materials, such as flyers, stickers, circulars, and bumper stickers, tee shirts, hats, mugs, beverage cups, educational services for the education and dissemination of information concerning the detrimental effects of recreational drugs." This is highly ironic. It doesn't look like the phrase ever got off the ground, but if anyone out there has a "Drugs Are Loser Friendly" coffee mug out there, I'd throw it on EBay post haste. It's unclear going forward whether a Charlie Sheen-endorsed line of anti-drug bumper stickers and clothing is a wise avenue for investment.

Sheen Kidz

This one is more recent. In 2005, a company Sheen owns called Three Dog Par filed a trademark application for Sheen Kidz, a "couture children's sportswear line" of onesies, baby shoes and the like that now seems like a ready-made Saturday Night Live commercial. Who knew? It's unclear how active the company is right now, but according to the LinkedIn profile of Michael Berens, the company's former CEO, it did $15.5 million in wholesale in its first season of operation and moved $10 million of product in Japan. Because who doesn't want their three-year-old daughter dolled up by Charlie Sheen's mind? It's unclear what relationship the line currently has to Sheen, though. The trademark has been transferred to a company called Hit One Out; Berens is the president, and it was suspended in January for failure to pay franchise taxes.