I've tried the Mozilla-based open-source music player Songbird twice before, and each time I reluctantly retreated to iTunes for a variety of reasons: Songbird wouldn't play my DRM-encumbered iTunes Store tracks, it was cumbersome to use, it kept crashing or wouldn't start, etc.
But in August I stripped the DRM from my 50 encumbered songs by burning them to four CDs and then ripping them back. And then I heard that the latest version of Songbird (0.7) had a redesigned interface. So I decided to give it another try. And this time it stuck.
The major reason is the interface redesign, which has simplified the application considerably, making it much easier to navigate. But it also doesn't crash much anymore and has started up fine every time.
I've been using Songbird almost exclusively for the last few weeks, except when I need to burn a CD (which it still doesn't do) and during the occasional foray into the iTunes Store to see if it has DRM-free versions of songs I can't find in the Amazon MP3 Store, like Ministry's original recording of Jesus Built My Hotrod or The Damned's remake of Jet Boy, Jet Girl (sadly, it usually doesn't).
I even activated its scrobbler support, and it's been pushing my listening habits to my public last.fm profile, which feels uncomfortably revealing, although no more so than having dozens of my colleagues following my decidedly non-work-related tweets.
And I've tried out its Songkick functionality for automatically finding concert dates for the artists in my library, which feels like a killer feature, since it's so much easier than searching for concerts manually (or tediously programming Ticketmaster/Live Nation to keep me in the loop).
Finally, I've sampled its SHOUTcast internet radio integration, which seems like it could be a great way to get someone else to mix my daily soundtrack for me, except that I haven't yet put in the effort to find the stations I want to listen to from the overwhelmingly voluminous selection of them.
Overall, I'm pretty happy with Songbird. Support for burning CDs and better integration with the Amazon MP3 Store are the only major features I'm missing. The rest is just nits.
(Note: recent versions of Songbird supposedly play DRM-encumbered iTunes Store tracks just fine, although I'm glad to be DRM-free anyway and plan to remain so from now on by not purchasing any more encumbered music.)