Iconic Icons
The icons on the original Macintosh were simple 32 x 32 grids of black and white pixels. Nevertheless, Susan Kare was able to create some of the most easily-recognizable icons of all time, including a frighteningly realistic Steve Jobs, under these harsh technological restrictions.
Why is it that such simple forms can communicate what an icon represents so efficiently, while high-resolution and photo-realistic representations of real objects are often not immediately recognizable?
About 7 minutes into this UI and Us interview, Wil Shipley explains what makes an icon iconic. in his words, “An icon is supposed to be the minimum number of elements that suggests something.”
UIandus.com Interview with Wil Shipley from Keith Lang on Vimeo.
One example Shipley uses is the “Picasso” Mac logo. But along with Susan Kare’s icons, the only good examples of “iconic” icons so far are as old as the Mac itself. What are some more recent examples?
Leopard’s new folders, for all of their flaws, are very iconic in the sense of using few elements to represent their contents. In addition, each “stamp” into the folders can be represented with very few pixels, which allows Apple to use the same symbols for the smallest representation of each icon (16 pixels square).


An even better modern attempt comes from David Lanham in the form of Sticker Icons. Among the most radical reinventions of famous icons are Flash, Photoshop, and Preview:

That Torrent icon isn’t bad either. Small raindrops making up a larger one is both easily recognizable as a play on the word “torrent” and as a visual metaphor for what torrent applications actually do.
Such icons aren’t well-recieved in all corners of the Mac community. Using a simple, memorable design instead of a photorealistic metaphor for what an application does is often seen as overt branding.
Adam Betts had the following to say about Yojimbo’s icon, which he was given and asked to “gloss-ize:”
“I do understand that they were only looking for pure branding logo and not standard icon but personally I strongly believe that this kind of app is better suited for standard design […] The icon they went with is ugly as hell in my opinion. […] But do they work well as a brand? I’m afraid so.”
In this case, the “standard design” is a photo-realistic icon of a journal, which could represent a huge variety of things, one of which is Yojimbo.
BareBones carries this icon philosophy over from their resolution-limited “Classic” Mac days, when they sold BBEdit with a similarly iconic icon. Note that TextMate, a competing product created after the rise of Mac OS X, uses a photo-realistic pen and paper metaphor for its icon (one that bears similarity to TextEdit, Property List Editor, and nearly every other document-editing application on OS X).
Before I end this post, I’d like to give a dishonorable mention to what may be the least iconic icon I’ve ever seen attached to an application:

Hmm… what exactly am I looking at? I understand Brent Simmons made this icon himself, and I’m assuming that means it’s temporary, but it’s a bit ridiculous to expect a user to recognize your application by a monochrome close-up of the desktop icon (that blob on the left is supposed to be the top of South America, if you’ve never seen NNW before).
How could we make this a bit more iconic? Well, there’s already a universally-recognized symbol for RSS feeds, and with a little NewsGator branding and 3 minutes in an image editor, you get something like this:

I am by no stretch of the imagination a graphic artist, but I’m assuming you get the general idea.
Of course, icons are a bad way to represent applications and commands in the first place, and we’d all be better off dropping them for simple words, but while icons are the entrenched platform standard, they might as well be a bit more iconic.