Web fonts are an interesting mix of technology and intellectual property licensing.
I’m almost surprised that we, as a culture, have managed to pull it off, overcoming all the hurdles. But there are now several companies and methods to use typefaces on websites. I checked out the current options.
I’ve been looking for a new web font
Just having learned that Baskerville is the king of fonts (!), I thought it’d be interesting to try on my two Rails sites (WebLaws.org and OregonLaws.org). Currently they use Helvetica Neue for text, and I feel ambivalent about it. On one hand, it’s a beautiful font. But on the other, it’s the standard font on iOS, and while it’s stylish, it’s not so unique now. It also has problems with readability that I blogged about in detail.
Options I found for inexpensively trying Baskerville on a web site
- License: 1,000,000 page views per month on unlimited subdomains.
- Cost: $12.50 for one font weight/style per year.
- Pure CSS, hosted font files: URW++ foundry’s Baskerville T.
- Normal, italic, and bold would be $37.50/year ($3.13/month)
Baskerville FS by FontSite foundry
- License: unlimited web usage
- Cost: $13 one-time payment
- Pure CSS, own the font file, host it yourself
- (I don’t know the FontSite foundry – do they make decent fonts?)
ITC New Baskerville Roman by Linotype foundry via fonts.com
- License: 250,000 page views per month, unlimited fonts, unlimited web sites.
- Cost: $10/month.
- Many other Baskerville fonts here as well.
- License: unlimited commercial web use, SIL Open Font License
- Cost: free
- Javascript + CSS, hosted on the Google Web Font system
- Looks similar to Baskerville
Dogweather 
How about Open Baskerville, which is based on Fry’s Baskerville, a Baskerville derivative created by Isaac Moore, a punch cutter who worked for John Baskerville and is SIL-Licensed: https://fontlibrary.org/en/font/open-baskerville