Strangely enough, it's not iTunes that's made getting legal copies easy for me, tho, it's Amazon. Like anybody who started on DOS and remembers when building your own computer was pretty much the only real option, I have a deep-seated hostility towards closed formats. As such, I won't buy a song from iTunes unless that's the only way it's available. MP3, being an open format, can be played on anything that handles electronic music, and DRM-free MP3s are what Amazon sells.
What really blew my mind was stumbling on the "World of Jeeves & Wooster" album -- small run to begin with and LONG out of print -- buyable as MP3s from Amazon. Ker-YOINK! And today I picked up Depeche Mode's cover of "Route 66" and Weird Al's latest album ("Internet Leaks") ... all fast and easy. While I miss having an actual CD, I don't actually miss it that much, and it's rare that I ever actually play my CDs anyway ... generally having burned them to MP3s for playing on my computer. When I can buy and download it all electronically, quickly, cheaply, and easily, the physical medium itself becomes something of a fifth wheel.
Oh, and I'm finally getting into podcasts ... not to mention it's nice to be able to listen to "Marketplace" when I actually want to, instead of having to be sure I'm in the car between 6:00 and 6:30 p.m. weeknights or miss it.
Now if only Dark Adventure Radio Theatre would go the "MP3 download" route...