Depends on the country.

I researched it for Russia recently and apparently the law is much stricter about fonts here than in the US. Both the character shapes and the "code" are copyrightable so you ain't getting away with converting it into a different format either. Companies did get sued over this and did have to pay millions of rubles in fines and licensing fees for their past usage. Not sure about individuals but I wouldn't try my luck with any non-free fonts made by Russian designers.

I would suggest not pushing your luck with webfonts though, because in that case you are distributing the actual copyrighted "code" of the font, not just the minimally protected shapes that it outputs. There are services which crawl the web actively looking for pirated webfonts on behalf of foundries (and their lawyers).

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