If I had a lot of discretionary capital, I would spend less time looking for free fonts. Many of us acquire fonts because we like them. If you're in business—freelance or otherwise—you get them for client jobs. And if it's a big type family (such as Helvetica, Gotham, or Univers), you may be able to pass the cost on to the customer, But most of us don’t have what we’d call extra funds.
So here are places I go for reference and periodic free fonts:
Originally launched by Bitstream, the first digital type manufacturer. MyFonts.com has tons of fonts, usually the big brands and all professional. And usually full price. BUT, they do have periodic sales or free downloads if you get on the mailing list. EX., I just took a survey and qualified for 15 free (professional) fonts.
The site was bought out by Monotype Typography (a very respected type founder from the days of metal). They provided the original Windows TrueType fonts, so they know about digital type. They have their own site, too, which is specifically for their own type, while the MyFonts.com site has a wider selection from other vendors.
The other site I have to use is the one that no one likes to admit to:
This is probably one of the biggest and most notorious free fonts sites around. Their offerings include anything and everything but it’s pretty well organized. Beware of fonts that lack a full character set. This might typically include (er, exclude): quotes, apostrophe, hyphen, asterisk and even a proper word space). Nevertheless, these problems are not insurmountable. And you might get just the right “look” for a project.
[EX. I just rejected an offer for a free font from an e-mail list to which I subscribe. It was one of those handwritten scripts that are in vogue right now. Being a bit of a type purist, I never thought I'd have any need for it. But this week, I ran into something that looked very much like it as a logo for a web site. And I said to myself, that's the type of request we'd get from one of our pro bono clients. They'd point to this as an example and ask for something just like it. Well, they haven't asked yet, but it enforces the rule/guideline that there's a purpose for every typeface design.]
If you need a text or “body” font, you would do better trying these sites. They have nice headline and display type, as well, but if your newsletter or brochure is just not making it with the Times, Baskerville, or Helvetica that came with your computer, you should look through the wide selection offered here. Even if they are not all free. All these sites have articles and newsletters, so be prepared to spend some time if you have any interest in Typography. These sites include newsletters, articles, and font identification services.
[Word of explanation: The alphabets are antique-looking (i.e., distressed) but very carefully drawn with full character sets including numerals, punctuation, monetary symbols and diacritics for all languages. They available at a few other font sites, such as DaFont.com]
Obviously, other manufacturers have their own web sites. If nothing else you can get ideas of similar fonts to look for; and they might even have stuff on sale.
Try Fonts.com, which is another Monotype Imaging showplace, and the FontShop originated by modern type design legend Eric Spiekermann. Again, both places have have lots and lots of helpful information about fonts and type design.
There are periodic sales from MyFonts.com or Linotype.com on the new revised standards, such as Helvetica Now and Metro, New Trade Gothic, Neue [New] Haas Unica.
Coming up: The last part of this article relates a real-life story about how I procured a good quality classic font for free (and how I overcame some of its shortcomings).