If you've ever owned an iPhone or an iPod, chances are you now manage your music using iTunes--because that's the way Steve Jobs wanted it. iTunes is pretty good, but it's not perfect. The duplicate killer that's native to the app, for instance, can be confusing and ineffective. The good news is that you can make iTunes better by using the following tips, tricks, and add-ons.
Drop your duplicates: iTunes does its best to let you know when you have duplicate tracks in your library (you can search for them by selecting File•Show Duplicates), but it's best simply isn't good enough. Free application Meta-iPod quickly digs up and clears out your dupes like a pig hunting truffles. Fire it up, and click the Start button to let it analyze your library; if it finds repeat entries, click the 2x button to view the duplicates, with Meta-iPod's best guesses for which ones you should save and which ones you should ditch. Then click the Delete checked tracks button to remove them.
Find free music: Though the iTunes Music Store isn't big on handing out free tunes, the Free on iTunes page hosts a regularly refreshed lineup of tracks, music videos, TV shows, and other special content for free downloading.
Remote-control iTunes: If you have an iPhone or an iPod Touch, you also have the best iTunes remote control money can buy. Download Remote to your iPhone or Touch (it's free!); pair it with your iTunes library (run Remote on your iPhone, tap Add Library, and follow the pairing wizard on the next screen); and then use it to control your iTunes playback, make playlists, and adjust the volume from Remote's iPod-like interface.
Clean up your metadata and album art: You could painstakingly correct every mislabeled track in your iTunes library, or you could let TuneUp do the job. This clever application scans your music, finds messy or incomplete metadata, and automatically fixes it, figuring out where all of your tracks by that versatile and prolific figure currently known as Unknown Artist really belong. Missing album art? TuneUp can take care of that, too. The limited program is a free download, but if your library needs a lot of work, you'll probably want to upgrade to TuneUp Gold, for unlimited metadata cleaning.
Let iTunes be your DJ: Want to listen to music selections that have something in common, without building a playlist of your own? iTunes' Genius feature creates playlists based on songs that it thinks (binarily speaking) sound good together or share a similar mood; and iTunes' DJ feature lets any guest with an iPhone or iPod Touch request, add, reorder, or remove songs from the DJ playlist on-the-fly, using the Remote application (mentioned above).
Automatically sync any iTunes folder: If you're like most folks, much of your iTunes library's music originated from ripped CDs and, ahem, unspecified online resources. Instead of adding new tracks to iTunes manually, point iTunes Folder Watch at any folder(s) on your hard drive, and this free app will automatically add new tracks to iTunes as soon as it sees them.
Get to know your smart playlists: Smart playlists do a great job of slicing and dicing your music into playlists without requiring you to spend hours sifting through every song yourself. Just set your criteria and let the smart playlist create itself. Make a best-of playlist from your most-played tracks added in the last year, for example, or rediscover songs with a smart playlist that looks for songs with a low play count.