How mobile can – and should – change the way we think about entertaining ourselves and each other.

Conventional wisdom has it that entertainment applications will be the key to unleashing the next great wave of handheld mobile activity. If only handset manufacturers and mobile operators could figure out just what games people want to play, music they want to listen to or content they want to access, the industry will get through its current doldrums and escalate to the next level. Everybody who needs a cell phone already has one, now it’s time to get the people who don’t need one. And in a world where we’re either working or playing, the only other avenue is entertainment.

But what is entertainment, really? The roots of the word may surprise you. To entertain literally means “to hold within” (tain, as in “container,” and enter, as in, well, “enter”). And for many centuries, this idea of produced fun being forms of entertainment has held.

In Ancient Greece, the epic storyteller stood in the village square and attempted to hold the street audience within his spell of words. The great theater piece is called “captivating” for its ability to hold our attention long enough to watch the hero succeed or fail. Film, which has for all intents replaced theater, has the advantage of a tremendous screen and special effects, making it all the more easier for its craftspeople to hold us within the worlds they depict. Most movie trailers now begin with the phrase “in a world where…,” only underscoring cinema’s potential to bring us into another place, and keep us there.

Even television – “the idiot box” or “the boob tube” – induces us to be “couch potatoes,” so entrapped by its hypnotic spell that we may not move for hours. All of our “entertainments” throughout history, from peep shows and carnival acts to NASCAR races and religious revival meetings, strive to keep us captive to the content, eyes open, jaws lax and passive to the story. Though we may be at the edge of our seats, the only place we have to fall is further into the world of the entertainment.

That’s why “interactive entertainment” has always seemed to me something of an oxymoron. The moment a person truly interacts, she is brought out of that spell. And even if we decide that the kid playing Doom is just as captivated by the world of her game as someone else is watching Jaws in a movie theater, what about when that kid begins playing a networked game with some other kid? Is she captivated? Yes. Is she held within a particular world? Not necessarily.

Handheld devices, in particular, have trouble holding our attention in quite the same way as IMAX screens and immersive environments, but they weren’t really meant to. I mean, how long can you stare at your watch? And even though a Gameboy can hook a 14-year-old into its Liliputian reality for hours at a time, and an iPod can envelop us (via earplugs) in its musical swirl, is the “entertainment” model of captivation appropriate for wireless mobile devices? I don’t think so.

These kinds of devices differ from mobile in that they are self-contained. The data on them is generally fixed for the length of the performance or game. The “entertainment” is a matter of exploring the databases or, at best, opening data structures in a new order, as in a computer game. Networked play, via mobile devices, occurring anywhere and at anytime, might actually comprise the opposite experience. Not captivation, at all, but liberation.

A playful mobile device need not entrap its owner within its own RAM. Rather, it can connect the owner with other people, the environment, or the temporal reality in new ways. Who is available? What is around me? What’s going on right now? Instead of enter-taining, these devices might do better to inter-tain us – that is, hold our connection to other people, places and things.

The mobile intertainment device depends not on captivation, but on introduction, orientation, and interconnection. Although very few companies are conceiving of mobile fun in this way, the early interest in services from UPOC and Dodgeball prove that people are seeking a different sort of fun through their phones – a fun that involves experiences with other subscribers rather than some company’s content.

Even information portals like Vindigo and Avantgo base their success less on what they provide themselves and more on how these pointers direct users to things in the real world that they want or need. A restaurant or movie recommendation is not the entertainment itself. It’s intertainment to entertainment.

Finally, self-publishing services like Phlog.net, which allow people to post moblogs and cell phone photos, promise a lot more than entrancement – they allow expression and connectivity. Indeed, there are a range of ways to have fun that may not involve what is traditionally known as entertainment.

While it may be more challenging to develop business models for user-generated social, artistic and self-expressive experiences, I think we have to accept this dilemma of our own making. After all, here we are declaring that mobile really is something new: a tide change worthy of massive investment, speculation, consumer interest and cultural attention. Are we ready to accept the fact that the interactive communication devices we’ve been celebrating may actually be worthy of the pitches we’ve been making for them?

I think so. And this means developing new approaches to mobile experiences, and finally evolving a two-thousand-year-old understanding of showing people a good time. The new rule of thumb, so to speak, may be to create experiences that do not contain the user but rather give the user a way out. Landlines are not radios, and cell phones are not Gameboys.

Wireless intertainment doesn’t involve people interacting with data; it’s about people interacting with the world or, at best, with one another. It’s time for the entertainer to end his song and dance, and make room for the next era of players. The industry winners will be the ones who stop thinking about creating the whole show, and learn simply to set the stage.