> Fonts should not be copyrightable. Print fonts are not, it makes no sense that digital ones are.
I agree with your first statement, except that I'm stuck re-wording it to "I wish fonts weren't copyrightable" because I can't find an argument/proper analogy that works.
I don't know the details around copyright law, IANAL (surprise!) either, so I'm looking at this from an incredibly naive legal perspective -- that almost everything is copyrightable (in the United States) except for facts. Since copyright law predates digital fonts, you have to look at things they are most like to see what applies (and find a judge to agree, but that part seems to be the simple). Print fonts are not copyrightable. I'm not sure why they're not copyrightable -- were they explicitly excluded (i.e. there's a law on the books that says "Print fonts are not copyrightable"[0]) or were they found to be "like this other thing that is excluded, so they are excluded, too".
Then, looking at what's similar about print fonts versus digital ones, there's not really a whole lot other than that they're "concepts" that represent letters in this context. One is chiseled out of some form of metal or strong material, is that size/shape permanently and though there's science/research behind it, for whatever reason, it didn't represent enough of a kind of work to warrant protection. A font has a lot in common on the surface, but underneath it's a program[1]. One could extend that to say "bitmap fonts are so similar to print fonts that they should be excluded" but one cannot say the same for TTF/others and I'd imagine.
The bigger problem, though, is that exclusions to copyright are basically never made any longer. This used to be more common, but the entertainment industry's money/power continues to extend copyright in ways that benefit them to the exclusion of other industries -- particularly software -- the large players have a lot of money, so a law that was designed to equally protect invention/creation (really, patent law was by-and-large aimed at helping individual inventors protect their invention/give them a chance to capitalize it against abusive larger competition) ends up helping secure the existing players positions.
Now, I don't know if anyone wants Warner Brothers to make Mickey Mouse cartoons, but I suspect there's a less heavy-handed approach to protecting long-held IP while not extending copyright, basically, indefinitely for everything.
So yeah, all of that to say "No, I don't think fonts should be copyrightable, either ... but I can say that for so many things and there's so much wrong with Copyright these days that it warrants revisiting a reset/rethink." Maybe one day!
[0] It won't be that sentence, it'll be a page worth of explaining why it doesn't fall into the various defined kinds of works.
[1] TTF hinting is turing complete.