My favorite is a more subtle form which has been gaining traction. Bring a fictional product into the real world. It is easiest to piggyback on an existing product. Last summer, 7-11 turned some of their stores temporarily into Kwik-E-Marts and rebranded their Slurpees as "Squishees" after the Simpsons spoof. The 8-bit tie also comes to mind, originally an April fool's joke and now up for sale.
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It is often easier to stick with T-shirts since there are so many sites that do all the work for you. If you cater to more of a sophisticated crowd, consider stressing an idea rather than a character. The web comic XKCD offers an anti-velociraptor shirt. ThinkGeek offers a red shirt with the word "Expendable", a throwback to doomed crew members on the original Star Trek.
OK, what if absolutely have to merchandise a character? Try one with a smaller role, such as weighted companion cube plushies from Portal. One of the most beloved minor characters on Futurama, the Robot Devil, would make for a great refridgerator magnet.
There is a reason that trying different techniques with merchandise can be more profitable. It can be such a delightful surprise that it will make headlines and spread by word of mouth, becoming a meme.
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