I suppose you need Windows Media Player for horrible purchased .wma files or something?
Otherwise, I recommend Just Not Using It.
For playing mp3s and most other audio files, you can use Winamp. For playing most video formats you can use Media Player Classic, as part of the K-Lite Mega Codec Pack:
http://www.codecguide.com/download_mega.htm
For your iRiver, you can just organise your music in folders using Windows Explorer, can’t you? I’m not sure what you need Windows Media Player for really - the iRiver is one of the few great mp3 player devices that *doesn’t* need some silly program (like iPods need iTunes) in order to put music onto it.

Hi, Peter.

I used WMP because it came with Windows XP and I was happy enough with it to put up with its limitations. After yesterday’s upgrade, I’ve dumped it. I uploaded a neat freeware package called Media Monkey (technically, it’s crippleware, but the “crippled” version is very functional). And guess what? It took me less time to install it, transfer my playlists, and sync my iRiver then it had taken me to fix the creeping errors that accumulate in WMP — and all without slipups, files disappearing, the sync list mutating between connections, or the library developing meta-errors.

You’ve touched on the precise reason I bought an iRiver instead of an iPod. Simple to use and no proprietary b.s. I use eMusic as my main music supplier, which sells mp3 files without DRM. That’s right. No DRM. None at all. So no hassles; you can copy it to whatever player you like, etc., etc., so long your usage is within standard copyright laws. And it’s cheap. The only drawbacks to eMusic are (i) the subscription system penalises you for not using your allocation every month, and (ii) not many Big Acts let eMusic sell their music because of the lack of DRM. Mind you, if you like classical, jazz, or indie music, then eMusic is great. You won’t get U2 or Robbie Williams, but that’s not my cup of tea anyway. There are only a handful of artists I like that aren’t available, and I can always buy a CD the old-fashioned way if I really want.

BTW, Peter, I downloaded a few of your sample mp3s yesterday. You might have noticed me in your usage stats. I’m really enjoying them, and my son Alex found them on the iRiver and has been playing The Levee Breakbeats and Stolen over and over.

Ooh! Yay. I probably have one or two newer Raven tracks I ought to put up there…

We also, by the way, have a FourPlay shop now - http://shop.fourplay.com.au/ (I didn’t want to spam the blog before, but what the hell!) where we sell, of course. DRM-free mp3s :)
Hm, that’s weird - eMusic penalises you for not downloading enough in a month? Bizarre! I’ve meant to get onto eMusic fo a while anyway, ta for the reminder!

Yeah, eMusic’s subscription system gives you a number of downloads a month. If you don’t use them within the month, you lose them.

Hi Chris,
I’d say ditch WMP and try either:

“Easy H10″ (if your iRiver is a H10 series) [http://easyh10.sourceforge.net/] which makes uploading a breeze. I also use ‘Comparator’ for all my synching [http://softbytelabs.com/]

“Rockbox” OS [http://www.rockbox.org/] (to replace the inadequate iRiver OS) - this is an open source OS amazingly more feature rich than any Mp3 player OS I’ve ever seen. I works on most iRiver, iPod, Sandisk and many other mp3 players. I have been using it on my H10 20GB for the past 3mths and could never go back to the flashed OS that comes with the iRiver systems.

Even my iPod lovin’ friends have started the switch to Rockbox :)

Chris, if you really want to play music in a way that is DRM free, and just works in an easy straightforward way, get an iPod and just use MP3s and don’t use by anything from the ITMS. If you use eMusic, an iPod works fine, and you don’t need to use any of Apples proprietary stuff.