How to Improve Your iTunes Experience (Part 1) [Mac Only]

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I love my music and everything else that goes along with it. I love the fact that in my iTunes, every song is properly labelled, is nicely arranged alphabetically by artist and have their particular album artwork attached in high resolution. It is so much easier to search for the songs you want when almost all the fields (i.e. genre, artist, album, year) are completed. Every little bit of information helps Genius to find the songs which match the ones you are listening to, creating a playlist which suits your current musical mood.

I grimace when I browse though some of my friends’ playlists and most of the songs are labelled “Track 1, Track 2…. Untitled Artist”. They must have some kind of ESP or monumental memorizing ability to remember what track is by which artist.

Listening to music on iTunes can be more than simply “listening”. It can turn into a pretty interactive hobby which for me, has become an obsession. A fairly rewarding one, at least. Here’s how you can convert from mere music-listening to actively interacting and expanding your music experience. In this part 1, I’ll show you how to enjoy your current music collection.

How To Organize Your iTunes Library

This is the very first step to improving your iTunes experience. How can you truly enjoy your music if you’re not sure who you’re listening to? Label your music properly, fill in their genre (if you’re not sure of what genre your artist/album fall under, check the iTunes store by clicking the arrow link next to the album title. It might not always be 100% accurate as some might argue but it’s a start), rate the songs you like, enter the year it was released – you get the drift.

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I spend quite a lot of time doing this, especially after I get my hands on a couple of new albums. My friends think that I’m crazy for wasting so much time but in the end, it’s very rewarding.


  • It is easier to search for the song you want to listen to
  • Rated songs automatically gets added into “My Top Rated” playlist for quick access
  • Smart playlists get updated instantly when new song from a particular artist/genre is added to library
  • Instantly create playlists by year (eg. 90’s or Oldies) if you fill in the year it was released
  • Properly labelled songs make it easier to check for duplicates
  • It helps Genius find out which songs you’re listening to and find the songs which are similar by retrieving information from iTunes according to the artist, genre etc.
  • As your music collection gets larger, you’ll find more reasons to organize your music. If you have somehow labelled your songs but haven’t capitalized the first letter of each word and you couldn’t be bothered to redo them again, TuneInstructor can do it for you. It has a lot of other functions but I mainly use it to recapitalize some of the letters which escaped me.

    Add Album Cover Artwork To Your iTunes Songs

    itunes covert artThis is just eye-candy but it subconsciously improves your music experience. In addition to only using your sense of hearing, you’re now adding a visual sense. Wine connoisseurs use this theory – that when more senses are involved, the better the experience. That’s why they look at the wine (vision), swirl it (hearing), smell it (smell) and finally drink it (taste).

    The most reliable way to add cover art to your music is to do it individually by album. It takes a little bit of time and effort if you’re starting from scratch but it prevents mistakes from occurring. To do this, I use Amazon Album Art Widget. I find it very usable and almost always finds the cover art I’m looking for. Other applications you may try are Corripio and GimmeSomeTune (which I covered in a previous article).

    If most of your music have their artwork attached and you’re trying to find those little buggers which eluded you, there’s a very useful script from Doug’s Applescripts called Tracks Without Artwork To Playlist which will find the songs without any artwork and automatically add them into a separate playlist.

    Don’t Settle For Low Quality

    organize your itnues libraryStatic, buzzes and noise in my music really ticks me off. That’s why I always go for a lossless file format if possible. Right now, I’m settled on Apple Lossless but FLAC is still the most popular lossless format. Music, especially classical or jazz are better appreciated in higher quality because of their sophistication. In the long run, keeping your music in a higher quality, either lossless, 320kbps MP3 or 256 AAC will spare you from re-ripping your songs in the future once your taste for music quality has been acquired. For starters, don’t settle for anything lower than 192kbps MP3.

    If you need an explanation about audio files formats, a good introduction would be to check out the article I wrote about audio convertors for Mac.

    As I said earlier, FLAC is the most popular lossless audio format but unfortunately, iTunes doesn’t support FLAC. Previously, I had to convert FLAC files into another format which iTunes recognizes. Every time a music file is converted from one format to another, it loses quality. That’s something that makes me cringe. Granted, that loss in quality might not be audible but it’s a loss nonetheless. Then I found Fluke. Fluke is an utility that allows me to play FLAC files directly in iTunes without any conversion and hence, without any loss in quality.

    Sing Your Songs (Add Lyrics to iTunes )

    How many times have you listened to a song you’d really like to sing along then had to open your browser, search for the song’s lyrics and add them into iTunes? TunesTEXT is a very reliable widget which retrieves the lyrics of the song which you are currently listening to and adds them into iTunes – you don’t even have to lift a finger! Use this together with DesktopLyrics and you will always have your lyrics right on your desktop. No rogue lyric windows to deal with. Whenever you want to view the lyrics, use the Show Desktop Exposé hotkey and boom – sing-along time!

    That’s all for Part 1. In Part 2, I will focus on helping you to expand your music library and few other tips to really enhance your iTunes experience.

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    29 Comments - Write a Comment



    Dude, there’s mac scripts that organize EVERYTHING for you. I can’t believe you’ve wasted so much time doing it manually.

    They come with the added benefit of being FREE.

    You’re welcome.


    Yeah, I know about DougScripts. But no script can help you change the titles of songs from “Track 1, Track 2…” to their corresponding titles. That’s manual labour your can’t avoid.

    Unless you know a script which can magically obtain the artist and song title just by playing the song :)


    There are plenty of programs out there that can “magically obtain the artist and song title” even without playing the song. Check out which has reviewed several for PC and for MAC.

    I’m currently using Media Monkey. I right click on the artist’s folder and then choose “tag from web” and Media Monkey pulls everything from multiple sources (including amazon) and automatically fills in or corrects my existing tags. You can even review the changes before they’re made to quickly check for errors.

    Now….you’re welcome! :)

    Jackson Chung

    Hi Adam,

    Nice of you to drop by. Just a quick note to Mac users: Media Monkey is Windows only.

    Alan Sundry

    Media monkey on the PC, will organise and rename your files and folders based on Tags, it will also retrieve tags and album art from amazon etc

    Blows itunes away for organizing


    Yea well not a script, iEatBrainz. Great for all those track 1, 2s and misnamed tracks as well.

    Timothy Andrew



    Lorne Easton

    Actually, transcoding FLAC->Apple Lossless is NOT lossy. They are both lossless formats. One problem I would point out with Fluke is I believe that it does not support Airport streaming, as FLAC is not a native iTunes format. Try Max: to convert FLAC to ALC.



    Dude, me and you are kindred spirits. I have always organized my enitre library so meticulously that it has become a problem. In fact, this summer when I hit 20 000 songs, I said that it was an addiction not just a hobby. And a serious addiction that needed to get taken care of. Now, only a couple of months later I am at 28 622 songs! yikes. Anyways, I always convert my new music into 128aac, and everyone of my tracks are in that same format now. Keeps my library a little slimmer at 100+GB. Anyways. Talk about scripts next time.


    Dan Warne

    Love that desktop background! Where can I get it?


    Sorry, that’s one of a kind – I made it myself!



    I can understand the obsession as I have had it ever since my first download from Napster. I just wanted to point out that transcoding between lossless formats does not degrade the quality.



    you need to get out more



    great tips man, thanks. looking forward to part 2. what is that program/widget you have on your desktop in the bottom right that displays album art?




    I thought I better clear up either a confusion that you have with regard to lossless audio conversion or a hard to understand part of your article so other readers are not lead astray.

    You mention that “Previously, I had to convert FLAC files into another format which iTunes recognizes. Every time a music file is converted from one format to another, it loses quality. That’s something that makes me cringe. Granted, that loss in quality might not be audible but it’s a loss nonetheless.”. Since Flac is a lossless format, you can quite happily convert it into any other lossless format, such as Apple Lossless or Wav without any quality loss. That’s the point of a lossless format – nothing is lost when it is converted from one one into another. It’s akin to a specially designed zip/rar algorithm for PCM audio.

    Naturally, your concern is valid if you were converting Flac tracks into a lossy format, such as Mp3 and Ogg Vorbis. Each time an audio stream is encoded with a lossy format (which are designed to reduce the size of the file substantially) quality is lost from the original input stream. Your statement “Every time a music file is converted from one format to another, it loses quality” is only true if you’re talking about lossy formats. Lossy to Lossy results in quality loss, Lossy to Lossless results in no quality loss, Lossless to Lossless results in no quality loss and finally Lossless to Lossy results in quality loss.



    I think the cover app shown in the screenshot is CoverSutra.



    An other good little application is Tune•Instructor that will help you automate some of the stuff in iTunes.
    It can be downloaded from apple here:



    I’ve recently started to organize my iTunes library, and I have to say, looking for the lyrics takes so long! Does TunesTEXT work for music in other languages, mainly Chinese?

    Jackson Chung

    Depending on the popularity of your songs. Asian songs take a little longer to find because of translation and transcription into the latin alphabet. AFAIK, TunesTEXT works for Japanese songs because one of its databases is Utamap. Not entirely sure about Chinese songs and I can’t test it because I haven’t any!


    Particle Man

    As this is Part 1, perhaps I’m jumping the gun here, but for a further improved iTunes experience, I set the playback sound enhancer to High, manually configure the EQ, and (on Mac) use You Control: Tunes to control iTunes with global keyboard shortcuts.



    My unique itunes experience would be spending nearly two hours creating ringtones for my iPhone 3G using the music from iTunes library(unprotected music only).
    i followed the step by step guide and finally got it.

    Very rewarding!



    This is a great little addition for your iTunes.

    can’t wait for part 2



    Is the fee for Coversutra a one-time fee, or is it monthly/yearly?


    Coversutra is only a one time payment, and I can really recommend this software! I bought it in a bundle for about half a year ago and have been really happy with it, and it looks great too!


    Jonathan Koontz

    Hey Jackson! I didn’t know how to get your e-mail so I’m sending you a comment. Hope this isn’t too tacky.

    Anyways, my name is Jonathan Koontz, and I am part of a video discussion startup team that will be launching next week called Vokle. Our project is a community network site based upon free browser-based video chatting and social bookmarking. Imagine a super advanced, super simple digg and stickam mashup built around live video chatting and killer usability…we’re proud to say it’s an internet first!

    Our project has been fueled by the frustration towards censorship in mainstream media, which is, of course tragically affecting the global climate in a myriad of ways. We want to provide a platform for people to speak their minds live about current events of all categories, and in the process, maybe, just maybe, raise the collective IQ of the nation!…hopefully!

    With an important election rapidly approaching, we’d like to present a better platform for users to speak up and speak out as soon as possible, so we’ll be having an exclusive invite demo the day before we launch, on October 29th. It would be perfect for you to swing by. We would love to get your take on it.

    Thanks again, and hope to hear from you soon.


    Sounds interesting. I’ll pop on over. Thanks!


    Tsuragi Kim

    sounds like a kick ass site. when does it lunch? i mean..launch hehe >.<



    Do you have like 100 albums or so? Or have you been organised since day one with song tags. Ive just switched to itunes and out of the 2100 albums or so id say 500 have artwork and are organised, its gonna take me a long time to get ontop of it all.


    Hmmm nope I have around 800 albums and getting them sorted the first time is the most challenging part. Now, as I add new albums, I make sure that I get it right.

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