In addition to sid's excellent writeup, I'd like to add that Penn has made a sincere attempt to involve himself in the computing community in a variety of ways, including sleazing around on The Jungle (his personal dialup BBS), working on an odd project or two at the MIT Media Lab, and writing a back page column for PC Computing magazine, among other things. He mentioned in his .plan once that his intention was to learn something other than show business so he wouldn't end up like some "bush league Chevy Chase".

Penn latched onto computers in the late 1980s, so by the time Wired magazine wrote an article about him in April 1994, he already seemed like a fixture on the scene, and with a fairly impressive rolodex as well. He had a finger-able UNIX account at, access to politicians on technology policy issues, and was rarely seen without the newest, flashiest laptop available.

Don't get me wrong; it's not like Penn cranks out C++ code (at least not as far as I know), but it's somewhat refreshing to see that he cares about something other than screaming into a cell phone and surrounding himself with yes men.