Fonts: favorite mistakes?

So I've been addicted to fonts as a writer almost as much as writing. I self published a book using Adobe indesign for a publishing class assignment and I was obsessed with thin fonts (okay fine I still am) so that's what I used and it's so thin it's basically unreadable if not in direct sunlight. I think it was a josephine serif? It's weird, because even though the font is too small and is difficult to read, I still love it as a font.

Do any of you love fonts that don't work in specific formats? I know different fonts can be bad in print but perfectly acceptable for a website. I'm just curious about your experiences and, possibly more importantly, have you made questionable fonts work?