Someone has collected links to 300 downloadable TrueType fonts* that the site-owner describes as essential. I wouldn’t go that far, and I have qualms about the inclusion of some Bitstream fonts (identifiable by the “BT” marker at the end of the font name), but I thought some readers would like a pointer to the site anyway.
The 300 includes a number of Nick Curtis’s designs (Mac users note that despite the restrictive warning, PC TrueType fonts should work under OS X); I’d just as soon go collect his all at once. Typefaces from the Apostrophic Type Lab appear here. I download most of Manfred Klein’s typefaces on his Sunday site updates — though by now he’s produced so many fonts that I can’t imagine being able to browse among them to choose one to use. Dieter Steffmann no longer makes fonts, but he has left a sumptuous treasure of type for other users. Paul Lloyd has resumed type design, and he’s contributing to the Blackletter collection and the Piratical collection. Harold Lohner offers some of his monthly updates for free download, too.
Not every one of these fonts attains the very highest standards (especially for kerning), but if one’s concern is for free typefaces, these are my favorite sources.
*I’m giving up the struggle to use words strictly by reserving “typeface” for the design of a particular character set and “font” for a complete set of a given size of a typeface. That just seems irrelevant at this point — so “font” and “typeface” have become functionally synonymous.