Obviously you need the right design at the right time, but it doesn't cost much to get a shirt ready for production, so if inspiration strikes it can certainly be financially rewarding to ride that pop culture wave.
If you have the channels to get it out there I would say yes but you definitely have to strike while the iron's hot. A friend and I waited too long and ended up not doing our "BRITNEY IS THE NEW WHITNEY" shirts because she dropped out of the news.
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