As for fonts specifically, while I am not qualified to describe creative elements versus prior art, I think we can all agree the the field of commonly used fonts is quite well within the realm of the public domain. Font foundries only exist to squeeze unearned profits from only minor and non-expressive additions to that that is already well within accepted public art for many hundreds of years. They are swindlers and con artists.
Note: US law (for rather obvious reasons). Europe (depending on the country) has either a design trademark or a design copyright available, which means that foundries can (in theory) control their use there (in practice, uniform worldwide licensing means they go for the lowest common denominator). Asian (mainly East Asian) IP laws does have a nuance, which means that whether a design is copyrightable depends if the purpose of the said design is utilitarian or artistic.
That's not true. Distributing letterforms wouldn't be a copyright violation. But if the font distributor shows the buyer some text and requires them to click "I Agree" before downloading the font, then they have a valid contract, which can impose whatever obligations they want, including usage restrictions.
Note that copyright licenses may not always be contracts, in cases where the recipient doesn't explicitly agree to them. Notably, the GPL is designed to work without needing agreement. From the GPLv2's text:
> You are not required to accept this License, since you have not signed it. However, nothing else grants you permission to modify or distribute the Program or its derivative works.
Though, the GPL has been enforced in the US as a contract anyway. [1]
But license agreements which you have to explicitly agree to are unquestionably contracts and enforceable as such.
Contracts are somewhat more difficult to enforce than copyright. You can usually only recover actual damages rather than statutory or punitive damages, and you can't use the DMCA as a shortcut to enforcement before going to court. But that's far from saying they're not enforceable at all.
[1] https://www.theregister.com/2017/05/13/gnu_gpl_enforceable_c...
> if the font distributor shows the buyer some text and requires them to click "I Agree" before downloading the font, then they have a valid contract
Right. But if they don't agree, then no legal mechanism exists to keep the "customer" from getting those shapes from someone who doesn't impose a contract, since anyone can peddle the same letterforms without violating copyright.
Sure, if you clone the font. But if you clone the font you can also distribute the clone as a web font. What's the difference?
Even without. Many use cases in print and other traditional, non-Web media exist where a clone wouldn't be required, because the end result is "flat", and you're not dealing in live text objects, unlike on the Web. You're shooting a fixed target. For example, it doesn't matter whether you reproduce a font's "fi" and "ff" ligatures if the blurb or logotype you're working on doesn't have those sequences. Worst case scenario, a person can get by with brute force—tracing the letterforms that they need. It's not as the operations to do that is any different from the kinds of edits they're already doing, anyway.
For either of the hypotheticals here, it would be possible to operate in the way described, subject to some constraints. There is no reason to think that the courts would perceive any legal imperative to recognize the distinction between server licenses or otherwise on copyright grounds. Companies can't invent law and say that it applies just because they wrote down how they'd like for things to work.
The technical reasons referenced earlier are what make these hypotheticals untenable, not law.
Foundries don't license fonts for "desktop use" on seemingly generous terms out of the goodness of their hearts. It's because they have no choice. Letterforms are not copyrightable. The font file†, however, is. Once a typeset character sequence is printed or rasterized and flashed on the screen, any license that a foundry cooks up trying to control that use would be unenforceable. The only leverage they have is controlling the distribution of the file. As it turns out, due to the way Web fonts work, this means they do have leverage on the Web—for technical reasons.
If the foundries had a choice, they wouldn't opt to license Web fonts more generously, they'd opt to extract more money out of the traditional uses.
(Note that this is written from the perspective of the way that copyright works in the US.)
† EDIT: I realized just now while brushing my teeth that this might lead to further mistaken understanding when put this way. So pretend instead that I said something like "what's in the font file", and pay particular attention to <https://ansuz.sooke.bc.ca/entry/23>.