If you're not averse to spending a little money for a fantastically useful app and to running a proprietary, nonfree program (but then again, if you were, why are you using the DRM-laden iTunes Music Store?), CrossOver Office from CodeWeavers is a great way to get your iTMS fix. As a bonus, you'll also be able to run other Windows-based, proprietary programs, such as Microsoft Word, Excel, PowerPoint, and Internet Explorer, as well as multimedia apps like QuickTime and Shockwave. The advantage of CrossOver is that it makes it really easy to run these Windows programs in Linux, and you won't be skirting the terms of their software licenses. The disadvantage is that CrossOver costs $40, which is, IMHO, a pittance for all that it offers you. If you're not sure if you want to buy the program, you can try it for free for 30 days, which should be plenty of time for you to kick the tires and discover how useful this program really is.
To start with CrossOver, head over to http://www.codeweavers.com. CrossOver Office is featured prominently on the home page, with a big red Try Now button that you should press. Follow the instructions on the page and download the software via FTP, BitTorrent, or HTTP.
After downloading the CrossOver shell script, you need to make it executable and then install it. Both actions are performed as a normal user, without sudo:
$ chmod 744 install-crossover-standard-demo-5.0.1.sh
$ ./install-crossover-standard-demo-5.0.1.sh
A GUI installer will open. Click OK to accept the quite reasonable licensing terms (basically that you won't copy the software and let everyone in the world use it), and then you'll be asked where you wish to install the software. By default, CrossOver will install at /home/
The program installs, and immediately the Introduction Wizard opens so that you can tell CrossOver about your Internet connectivity. Click Next, and you'll be asked if you use an HTTP proxy. Most likely you don't, so click Finish; if you do, enter the correct information and then click Finish.
You're back at the main Setup screen, but now there's a new button: Install Windows Software. Click it, and the Installation Wizard opens, displaying a list of supported Windows software, including various Microsoft, Adobe, Intuit, and other companies' apps. Scroll down until you see iTunes, and then click Next.
If it's not clear by now, you are expected to own a license for the software you install, or install freeware like Shockwave and QuickTime. CodeWeavers is a legit company and is not going to provide you with copies of software you're supposed to purchase.
The first screen of the install tells you that CrossOver is going to download and use iTunes 4.9.0, and that you should avoid upgrading. Listen to the folks at CodeWeavers! They test this stuff, and they know what they're talking about.
You're given a choice between the Express and Advanced install; go with the Express unless you absolutely know what you're doing and need the Advanced option. Click Next. CrossOver will download and install iTunes for you, and the whole time Apple's program will think it's running on Windows instead of Linux. I'm not going to walk you through an installation of iTunes, since presumably you're already familiar with how to install (and use) it. It's mostly just Next, Next, Next, anyway.
When CrossOver finishes, you'll reach the end of the Installation Wizard. If you're ready to quit CrossOver, click Finish. Before doing so, you ought to check the box next to "Remove installer files" so you can keep your hard drive tidy. If you had a problem with the installation and you want to help CodeWeavers diagnose the issue, check the box next to "Package log for CodeWeavers support," which saves a logfile detailing the process, so that tech support has some useful info. If you want to place more software on your system, check the box next to "Install more Windows software," which starts the wizard over again. Finally, "View installed associations" shows you what file types are now linked to the program you just installed. It may be handy to see, so feel free to check it.
Now that iTunes is installed on your Ubuntu machine, you'll find a shortcut for it on your desktop, as well as on your K menu (if you're using KDE) or Applications menu (if you're using GNOME). Start up the program, and you can buy as much DRM-laden music as you'd like.
I'm not really a fan of iTunes, or DRM in general. For my reasons why, see an article titled "The Big DRM Mistake" that I wrote for SecurityFocus, available at http://www.securityfocus.com/columnists/390.
If you ever want to uninstall iTunes, go to your K menu or Applications menu, and then to CrossOver Configuration. Select iTunes, and simply press Repair/Remove.
I've used CrossOver to run a wide variety of software; in fact, I've written several books using the VBA-laden Microsoft Word templates that publishers love so much, and they've run beautifully under CrossOver. You'll find that CrossOver is an incredibly invaluable tool that can already run a lot of important Windows apps, including iTunes, with the list growing all the time. Try it out for 30 days and see what you think.