Keith Houston writes about the history of punctuation marks, symbols, and typographical characters, which became his book Shady Characters.
HN commenters recommend it and the related book, praising series on the interrobang and emoji as informative and favorites on the topic.
If you need something free/opensource, there’s not many options. When you like it old-school, you can give Knuth’s companion to TeX MetaFont¹ a try.
Then there’s FontForge², which is by far the most evolved, feature-heavy project, but until recently had bad UX/UI and was a pain to install and run on OSX. It seems, that’s changed, though.
FontLab³ still is the type design “industry”’s de facto standard font editor, but development lags behind, and it’s quite expensive for a hobby project.
There are a few other proprietary offerings, notably the DTL FontMaster⁴ tool suite. But Glyphs⁵ seems to be going the winner, steadily taking over market share from FontLab.
If you like scripting your designs (esp. in Python) you should definitely try RoboFont⁶.
When you’re looking for volunteers/collaborators on your project, then do check in at Typophile⁷. For over a decade, it’s the principal outlet for all things type and type design: on the fora you’ll meet some very knowledgable experts always willing to help.
Since you mentioned punctuation, I suppose you’re familiar already with the _Shady Characters_⁸ project (and its companion book⁹). As for a detailed history, I can highly recommend Malcolm B. Parkes† authoritative monograph on the subject,…
> It wasn't a letter of the alphabet any more than the dollar sign, the pound sign, or punctuation were letters of the alphabet.
I'm not aware of historic English alphabets that include the dollar or pound sign or any sort of punctuation. On the other hand there is a lot of evidence of & being part of the alphabet. Wikipedia has or links to plenty of cases:
* Old Saxon alphabet: https://en.wikipedia.org/wiki/Old_English_Latin_alphabet#/media/File:John_Fortescue,_The_Difference_between_an_Absolute_and_Limited_Monarchy_(1st_ed,_1714,_Saxon_alphabet_page).jpg
* The Dixie Primer, for the Little Folks: https://docsouth.unc.edu/imls/moore/moore.html#moore5
* Byrhtferð's Old English Alphabet: https://www.evertype.com/standards/wynnyogh/thorn.html
* My Own Primer, or First Lessons in Spelling and Reading: https://shadycharacters.co.uk/2011/07/the-ampersand-part-2%C2%BD-of-2/
None of these are songs.
This article takes its content from the book "Shady Characters: The Secret Life of Punctuation, Symbols & Other Typographical Marks" by Keith Houston. The book originated on his website as a series of articles, the "&" ones are:
- The Ampersand, part 1 of 2 (https://shadycharacters.co.uk/2011/06/the-ampersand-part-1-of-2/)
- The Ampersand, part 2 of 2 (https://shadycharacters.co.uk/2011/06/the-ampersand-part-2-of-2/)
- The Ampersand, part 2½ of 2 (https://shadycharacters.co.uk/2011/07/the-ampersand-part-2%c2%bd-of-2/)
I'd highly recommend the website and the book, and also his new book "The Book" about the origin of the book.
The blog "Shady Characters" has a lot of great investigation about the history of the Octothorpe[1], and similarly the Pilcrow[2], Ampersand[3], and "commercial at"[4].
[1]: http://www.shadycharacters.co.uk/2011/05/the-octothorpe-part-1-of-2/
[2]: http://www.shadycharacters.co.uk/2011/02/the-pilcrow-part-1/
[3]: http://www.shadycharacters.co.uk/2011/06/the-ampersand-part-1-of-2/
[4]: http://www.shadycharacters.co.uk/2011/07/the-symbol-part-1-of-2/
This reminds me of Keith Houston's wonderful blog, Shady Characters (http://www.shadycharacters.co.uk/). Keith has written at length on the pilcrow, interrobang, and sarcasm marks (all touched upon briefly in this article) amongst other punctuation marks.
I am somewhat surprised that Shady Characters was not cited by the article. There is simply no better place to learn the surprising, entertaining histories of our punctuation.
Might I also recommend Keith Houston's wonderful book "Shady Characters: The Secret Life of Punctuation, Symbols, & Other Typographical Marks":
https://shadycharacters.co.uk/books/shady-characters-the-book/
He also posts, with some regularity, to his blog on the same topic:
https://shadycharacters.co.uk/
Employing the correct usage of hyphens, en dashes and em dashes continues to be a small daily joy for me.