The Past and Present of Web Typography

The core four: Georgia, Verdana, Arial, and Times. Familiar to most, as the web safe fonts. All solid choices for maximum compatibility. Nearly all of computers show them accurately (as shown below).
Update: Type designer Rod McDonald provided corrections to my sloppy wiki-research.
Times New Roman
Being in the spotlight for just short of a century, Times New Roman became ubiquitous. Designed for the British Times newspaper in the early 30’s. It’s popularity in book publishing and wide use paved its way into the digital age.
Rod says: Times New Roman was originally designed for The Times of London by the renowned typographic historian Stanley Morison who employed Victor Lardent to do the final drawings. The fonts were produced by the British Monotype company.
Georgia
Matthew Carter is one of this generation’s most prolific and best known type designers. His work has changed the face of the web. Subtle variations in x-height, weight, and size makes it better suited for screen presentation.
Rod says: According to Matthew Carter, Georgia owes much of its design to the old British Scotch Romans and to his own Miller typeface. Carter made the serifs considerably heavier to ensure they would ‘hold up’ at small sizes on screen.
Verdana
Another Matthew Carter creation. This time a sans serif. Much like Frutiger. It’s exceptionally easy to read at small sizes.
Rod says: Matthew Carter’s Verdana is similar in design to Walter Tracy’s 1959 Adsans which was originally designed for use at very small sizes in the classified section of newspapers. Another influence on the design was Carter’s 1977 Bell Centennial, designed for use in US telephone directories.
Arial
The result of Microsoft’s prevalence, and of the original and ever popular, Helvetica.
Rod says: Arial was developed by Monotype for IBM in 1982. The design was based on the old Monotype Grotesque range and was originally called Sonoran Sans. In 1993 Microsoft asked Monotype to provide them with a TrueType sans for their new Windows 3.1 OS. Monotype reworked Sonoran Sans and renamed it Arial. Shortly after its release false stories began to circulate that Arial was simply a ‘knock-off’ of Helvetica.
Want to use another font?
With pressure from designers for more choice, developers have taken up the cause. As a result, font replacement was born. After a web page loads, HTML tags (usually headings) are replaced with either vector outlines or images taking on the dimensions, overlapping, and replacing the original heading.
The following are essentially workarounds as browser technology is slow to adapt and font foundries are weary of internet distribution and piracy. Font replacement on a large scale (body text) is unwieldily by its resource hungry nature. But, for headings, they work splendidly to enhance the look of your site. Here are a few of the most well known…

sIFR 2.0 (or sIFR 3beta), The most popular font replacement. In part, because it’s the only way for the heading to remain selectable. You need flash installed in your browser to see anything, and it’s notoriously difficult to setup. (requires Javascript and Flash)

FLIR or Facelift Image Replacement ( Pronounced fleer ) transforms type into an image. Because the result contains none of the original curve information, it allows you to bypass most EULA web embedding restrictions. The only drawbacks I’ve encountered have been its lackluster support for special characters (typographer quotes, em dashes, etc.), and loads a bit slower than the others. (requires Javascript and PHP)

Cufón is a no flash solution, like FLIR, but loads incredibly fast. Fonts are embedded into a javascript file where the outlines are extracted. Because of the possibility for reverse engineering, this method goes against many EULA agreements. Check your font’s fine print before using. (requires Javascript)

Typeface.js, much like Cufón, extracts and merges fonts into a javascript file. The main difference is that typeface.js only supports TrueType fonts, and detects file permissions. So, good luck for any font that isn’t free. (Requires Javascript)

Looking for a simple solution? Typekit uses CSS’s @font-face, hosting the font files for you (for a small membership charge). Choice is limited, however, as only a select few foundries participate. Implementation is as simple as pasting in a single line of javascript code. Because the fonts are securely hosted by Typekit, font stealing cheapskates will have to look elsewhere.
It’s a Step Forward, but…
In 5 years time, let’s all hope either Microsoft will get its act together with its EOT font format or there’ll be a web Opentype format that everyone agrees upon. But, until that date there’s many a workaround to employ.
Anything I missed to mention? Something to add? Please share below.
I’m a frontend designer/web designer/graphic designer/regular guy with an insane curiosity for web design, typography, and the art of visual communications. I love to write, and do so in the