I Deleted My Entire iTunes Library And You Can Too

TJ Connelly
Jul 10, 2015 · 8 min read

I’ve been using iTunes to manage my music library since it was first released in 2001. I’ve always been a music collector, and now I’m a professional DJ.

I do radio shows, sporting events, parties, parades, and yes, weddings. I’ve saved my playlist from every gig I’ve ever had. My iTunes Library has folders full of playlists for family, friends, and others along with mixtapes both natively digital and those I’ve reconstructed from actual cassettes.

Today I deleted my entire iTunes library: music, playlists and all. And you can too.

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The only real argument I’ve ever had with iTunes is DRM. In order to get record labels on board with the iTunes Music Store, Apple agreed to develop and implement FairPlay, a proprietary system for controlling access to downloaded content. iTunes itself set restrictions on burning CDs and connecting to shared music libraries.

In 2007, nearly four years after the Music Store launch, Steve Jobs wrote “Thoughts On Music”, in which he called upon record labels to abandon the DRM strategy:

Now, we have Apple Music. Added in the 12.2 release, the Apple Music story thus far has been a series of horror stories for the music collector: tracks mismatched or replaced, tags munged and deleted, and in one case a user reporting six million copies of a Lorde song had been copied to his library.

The most chilling development, however, came with the revelation that Apple Music could replace your local library with DRM versions of songs you’d already purchased. Whether the original source is the iTunes Music Store, Bandcamp, Soundcloud, or just a CD you purchased and ripped to your library, Apple would now control your ability to access your own songs, including locking you out of music on some devices purchased from Apple.

Analysis and accusations are flying back and forth in headlines, comments, and support threads with no word from Apple. After spending half the week reading every article I could find, I came to the first of two conclusions:

I am not (currently) at risk.

The iCloud Music Service allows me to upload my library and have my tracks ‘matched’ with their Apple Music equivalents. In the event a match cannot be found, Apple Music will upload my local track. Since I need to have my music on disk for work, I have no temptation to free up hard drive space and keep my library on iCloud, no matter how convenient it sounds.

As long as I never delete my local copies, I should be safe from Apple Music DRM.

The second conclusion is far more dire:

I don’t trust Apple with my music anymore.

I’ve been an Apple user all my life. I wrote Logo programs on my school’s Apple II’s. My first computer was a Mac SE 30. I took shit from the other indoor kids in high school for using a Mac and I was never tempted to change.

When Apple announced iTunes, I rejoiced. Thus far my digital music collection had mostly existed on Linux boxes running xmms. The idea of having my music on my PowerMac G4, with a massive hard driveseemed like such a paradise I immediately started to wishfully spec out a PowerBook for DJ gigs. I could carry every record I owned in a box that weighed less than seven pounds.

Even when one of the 10.0 releases of Mac OS X destroyed my hard drive and by extension my nascent music library, I stuck by Apple. I built a larger and larger music collection, started working as a DJ professionally, and saved the playlist from every gig in iTunes.

Now I have a maxxed-out MacBook Pro, and even when iTunes pinwheeled the second time I opened it I took a deep breath and persevered. After all, I have 2500+ playlists managing tens of thousands of songs. I read some articles on library optimization, backed everything up a couple more times, and moved forward.

For any other piece of software, the bloat would be enough reason to punt and start looking for alternatives. But now, in a move reminiscent of the ultimate evil in the galaxy, Apple Music is bringing back DRM. And I’m out.

Help me Swinsian-Wan Kenobi, you’re my only hope.

Search ‘iTunes alternatives Mac’ and you’ll find stacks of articles discussing the same 5–8 apps. The clear standout is Swinsian, a word I have become far more used to typing and saying aloud in the last week.

Swinsian looks and feels like what iTunes would be if it had stuck to being a music player and library manager. The software is $20, and offers a 30-day trial period free of charge. The app has easy functionality to help you migrate from iTunes or run in parallel, so you can try it out for a few days without having to commit and make the leap.

The second item on the File menu is “Import iTunes Library”, which works perfectly. Previous versions couldn’t import Smart Playlists, but the current release handles them perfectly. The terminology is all the same between the two apps so there’s not much of a learning curve.

The app will set up a library folder at by default. When you first import your iTunes library Swinsian doesn’t move anything, so your Swinsian library references the files in your iTunes Media directory. This is the time when you should play around with the app a bit and see how you like it. For me, the ease of use along with the return of playlist windows and the addition of regex-powered search were easy clinchers. And Swinsian is not a perfect solution: there are a few drawbacks. If you’re ready to make the leap, read on.

How To Delete Your iTunes Library

I won’t lie: this was a little bit terrifying, or at least as terrifying as any other experience you can have sitting at a desk. I checked my backups like four times and was still nervous I’d wake the next day to discover a missed checkbox has vanished my playlists, or sent my music to the big iCloud in the sky.

My end goal was to move all the music out of iTunes and leave things like Movies and TV Shows behind so I can still make use of my Apple TV. I don’t particularly care about things like Date Added and Watched status for these items, so I was free to handle this fairly simply.

If metadata for your non-music media matters to you, do not follow these instructions. Otherwise take a deep breath and follow along.

1: Back Everything Up.

Make sure you have a full copy of your iTunes Media folder along with your ‘iTunes Music Library.xml’ and ‘iTunes Library.itl’files on an external drive or three. We’re only focusing on the Music folder in iTunes Media, but if you aren’t already backing everything up you should be.

2: Import iTunes Library

Probably you’ve already imported your iTunes Library as mentioned above. My import was fairly smooth, though Swinsian did grab some extras I wasn’t intending to include like TV Shows and Podcasts. You can repeat the import if you’re not sure, just be aware the process will bring back files you may already have cleaned up.

3: Make Sure You Have Everything

Reviewing every track in your Library is impractical (at least for me) but do some casual checks to make sure playlists look right and you have roughly the same number of tracks in your Swinsian library that you do in iTunes. Once you’re satisfied, quit iTunes.

4: Consolidate Library

In Swinsian, open the Swinsian->Preferences->Library pane.

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Boldly click the ‘Delete originals after copying’ checkbox.

With great resolve, click ‘Consolidate Library…’ and confirm that choice in the dialog box that follows.

Wait patiently for this process to complete.

At this point you’re 95% of the way done. All of your music and playlists should be imported to Swinsian.

5: (optional) Collect Detritus

Assuming you haven’t put your iTunes folder somewhere crazy, open a Terminal window and type the following (you can cut and paste if you like):

Everything you see listed is what’s left in your Music directory. In my case this was a bunch of scattered PDFs and image files attached to Deluxe editions of albums I’d never really looked at before. For safety’s sake, I created a new folder in ~/Music called ‘iSkeleton’ and moved my iTunes Media ‘Music’ folder to it.

6. Delete iTunes Library Files

Arguably the truly logical move here is probably to delete all the music listed in iTunes and carefully delete every playlist one by one. In my case this would take actually forever, so I didn’t go that route for the reasons outlined above.

Again, I first backed these files up to my new ‘iSkeleton’ directory. I’m paranoid; your call.

Navigate your way to ~/Music/iTunes/, drag both ‘iTunes Music Library.xml’ and ‘iTunes Library.itl’ to the trash, and empty it.

7. Reopen iTunes

The light is green, the trap is clean. All my music and playlists now live in Swinsian.

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Rather than allow iTunes to scan for media, I re-added my other media folders (‘Movies’, ‘TV Shows’, ‘Podcasts’, etc) to my library and now I have a great little app for streaming to my Apple TV.


As mentioned in the Swinsian FAQ, if you want to use a mobile MP3 player it won’t be your phone anymore. I picked up a refurbished 80G iPod Classic for $150 on eBay and it’s working great for me. I had forgotten how much I enjoyed the tactile experience of a clickwheel and I can actually carry more music than I did before.

The strangest part of this whole experience? Dragging the ‘Music’ app on my iPhone from the dock to the folder on the last screen with all the other useless built-in Apple apps.

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I have no idea what to do with all the space, but I look forward to spending a lot less money on the iPhone 6S upgrade this fall.

TJ Connelly

Written by

DJ @RedSox @Patriots @NHLBruins 🔊 host NPI @WZBC 🎙 startup founder, freelance music curator & software developer 💻 Dr. Dre said i was a good DJ once

TJ Connelly

Written by

DJ @RedSox @Patriots @NHLBruins 🔊 host NPI @WZBC 🎙 startup founder, freelance music curator & software developer 💻 Dr. Dre said i was a good DJ once

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