I think there is a lack of art and play in computing, particularly around more advanced subjects. While it is sensible for academic papers to be serious, and not to force readers to experience art when they are just after useful information, pretty much anywhere else it could fit fine in small amounts, without obstructing usage. While occasional jokes are not too bad even in papers.
Hacker culture combines both art and playfulness, and I think it is pretty much what I perceive a lack of.
Too often people are grumpy and serious even in online games, arrogant or solely profit-seeking around programming, use generic templates and stock images for visual design. The split between software for beginners and for advanced users seems unfortunate and related as well: seasoned programmers tend to be less motivated to make software (and GUIs in particular) a beginner computer user would like. The priorities and requirements change as one learns a subject, including computing, and perhaps those are beginner programmers (or simply younger people) who seem to be more inclined to incorporate some humor and creativity into their works, as well as to target beginner users.
There are occasional examples of such playfulness referenced from my collection of links. Such examples include demoscene, ASCII art, articles like those by James Mickens, perhaps the materials found on Gopher and telnet BBS, which are dominated by hobbyists, chatter on some IRC channels. Web comics and humorous websites in general, too. And games, and maybe some of the GNU projects, with their documentation. Of course more traditional and standalone forms of art and play are also around, including visual arts, music, writing, but here I would like to focus on those intertwined with computing.
Cyberpunk may be remotely related to this, although its connections to actual computing cultures (Internet culture, hacker culture, etc) seem rather limited.
The Phrack magazine combines relatively advanced topics with the additional fun ones (culture, style, art), but it is heavily geared towards security hacking in particular, which is reflected in the style as well. Other online magazines, as well as different kinds of media, can similarly gather communities around them, as can software projects.
artscene.textfiles.com hosts a large "art scene" collection (not just ASCII art, but also music, writing, demos/intros), while web.textfiles.com hosts e-zines and similar bits of information, adjacent to ASCII art and other fun with computers.
Maybe I will try to collect more of inspirational examples here, or to expand more on it, but for now this note is intended to work as a reminder to aim inclusion of more fun into produced works.