Those are the questions I pondered while playing with my new video-enabled iPod ($299 for 30GB, $399 for 60GB). Apple's handheld player is easily the slickest I've ever seen. Video playback is sharp (the smallish 2.5-inch screen makes it seem even sharper), and it's a snap to use. (See our full review of the iPod.)

What makes this iPod truly innovative is that Steve Jobs managed to convince Hollywood to loosen its death grip on content and allow shows to be sold on iTunes.com. Though this content is exclusive to the iPod, the deal could lead to a tsunami of video-to-go for other portable players.

The Vids Are All Right

At press time iTunes served up more than 2000 music videos, a half-dozen Pixar short films, and a handful of TV shows--including ABC's Desperate Housewives and Lost, as well as NBC's Law and Order and Surface--for $2 a pop. You can view 30-second samples and pithy summaries of each episode, like this one for Desperate Housewives: "Gabrielle causes a prison riot while visiting Carlos, while Lynette learns that Parker has an imaginary friend." Who could resist that? I immediately bought it along with four Green Day music videos.

Purchasing video content from iTunes and moving it over to the iPod is a breeze. Click the Buy Video button and enter your account name and password, and the file starts downloading. Plug the iPod into your computer's USB port, and the file transfers automatically. It took about 12 minutes to purchase and download 200MB worth of data on a cable connection and a few minutes more to transfer the video files to the iPod.

But transferring other video is less snappy. You have to use Apple's iTunes software, which is mighty finicky about the types of video files it supports. To transfer home movies or other unsupported content, you'll need to buy a copy of QuickTime Pro ($29) and convert the files to the iPod's H.264 MPEG-4 format. (So much for Apple's famous devotion to ease of use.) You can also try a third-party tool such as the free Videora iPod Converter. With Videora I could convert AVI and MPEG-2 files, but I had less luck with other formats.

TiVo also has announced it will let subscribers transfer shows they've recorded to an iPod or a Sony PlayStation Portable, though details were fuzzy at press time.

Dearth of Content

Other players have their own content problems. If you have a Windows Portable Media Center like Samsung's Yepp YH-999 ($500) or iRiver's PMC-120 ($550), you can use Windows Media Player 10 to convert home movies into a viewable format. You can also record shows on a Windows Media Center PC or TiVo Series2 and export them to the PMC, spend $20 a year for news and sports clips from MSN, or rent films from CinemaNow. Otherwise, video fare is hard to come by.

AOL and Warner Bros.' In2TV network plans to stream old shows like Maverick to PCs for free (with ads), but without support for portable devices. NBC and CBS will sell shows on demand for 99 cents apiece, but only for DirecTV satellite and Comcast cable subscribers. For now, most portable content is likely to come from video podcasts, which are a) usually free and b) worth every penny.

I like the iPod, but I can't say it will cure my TV jones. It's great for watching 4-minute music videos. But when I want to view a 43-minute show, I'd rather do it on my couch, with a Duff beer in hand, just like my man Homer.

Contributing Editor Dan Tynan is the author of Computer Privacy Annoyances, published by O'Reilly. Contact him at gadgetfreak@pcworld.com.