OS X open Flac files with iTunes - VLC to the rescue
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Ok, so you've gotten some high quality Flac lossless audio files, or are converting your CD collection to lossless Flac audio so you can carry it around on your hard drive. They aren't opening in iTunes, that's odd you tell yourself.

What's that you say? Nothing happens? iTunes isn't playing it? The NUMBER ONE and DEFAULT lossless audio file format in the world!!?? Not working in iTunes?

Why? Because flac cannot be use used at all in iTunes. This is disgusting, of course, and it's a blatant attempt by Apple to force you to use their iTunes profit generator store. So screw Apple, we'll use free software, which rides to the rescue for us.

First thing's first, let's check out the Flac main operating system tools page

What's going on here? I'll tell you what's going on. Apple wants you to go to iTunes store and buy their DRM encumbered proprietary Apple lossless or compressed formats. Why? Because iTunes is a HUGE money generator for Apple.

Install VLC and configure OSX to use VLC for flac
First download and install VLC free media player for OS X

Click on a flac files, and some other application is offered to open it with. This isn't what you want.

Please note, I can't use OS X without a standard 3 button mouse, it's too hard to find stuff in it, so I always plug on in to make the system more standard behaving.

So to change this default, I'm sure there is some other way to do this.

Right click on any Flac file, select 'Open With..', click 'Other..', this opens a new window, where you can set your default application. Basically the same as Windows has always been, that is.

In the new window, take the top drop down list and set it to Applications, then type in 'VLC' into the search box, and hit enter. Highlight the 'VLC' item, then click 'Always Open With', and click 'Open'.

Now your system should be set to use VLC (or whatever your default preferred audio player that isn't iTunes in OS X is).

Then you'll need to add the Media Library

:: Quote ::
From the "VLC" menu select "Preferences...". It will not matter which tab you select. The desired option is an Advanced option: in the Preferences window, in the lower left hand corner find radio buttons labeled "Basic" and "All". Click the "All" button.

The preferences window will change to show a narrow left-hand pane and a wide right-hand pane. The left pane lists categories of preferences that may be adjusted. Most items have triangles(Mac) or "+"(Qt) next to them, which may be clicked to show subcategories. For the moment we don't need to click any of them. Just know that expanded subcategories give quick access to particular options. Occasionally a subcategory may be the only way to gain access to the options desired.

If the left-hand pane is too narrow to view the list, click on the divider between the panes and drag it to adjust the width.

In the left-hand pane find and click the word "Playlist" to view the Playlist controls.

In the right-hand pane, next to "Use media library", ensure the box is checked. If it was necessary to change this option, be sure to click "Save", at the bottom right of the preferences pane.

On this control pane, note "Play files randomly forever" - uncheck this if desired. (Users have reported files playing in random order even when they don't want them to. For 0.98 it is uncertain whether this control is working. If you have not enabled it, but are getting random play, consider reporting it as a bug.)

To close this window, click either the "Cancel" or "Save" button.

Once "Use media library" is enabled, open the Playlist window to see the Media Library in action. There are several ways to accomplish this, but one certain way is: from the media player's menu bar,

* Mac: click "Window" menu and select "Controller...". The last time the VLC media player was used, if the playlist window was already opened, then it will automatically reopen. If not, then click the "Window" menu again and select "Playlist...".
* Qt: click "View" menu and select "Playlist".

Due to redundant controls, there are other ways get this done. On the basic controller, in the lower right-hand corner, is a pair of buttons. The left button when toggled will open and close the 10 band audio equalizer. (If you want to use it, be sure that there is a checkmark in the "Enable" box in the Equalizer's window.) The right-hand button when toggled will open and close the "Playlist" window. You can also open and close the "Playlist" window by grabbing and dragging the very edge of the lower right corner of controller window. At a certain shape and size, the "Playlist" window will snap opened or closed as appropriate.
To add files/folders to your Media Library:

1. Select "Media Library" in the left pane of the main window.

2. Right-click the Media Library area, and click Add Folder (or Add File)

3. Select the file/folder you wish to add, then click OK.

Note 1: to add to VLC media library, just drag and drop the folder to the 'Media Library' folder in the playlist viewer of VLC

Note 2: To sort the list, right click on the Media Library option and select Sort Node by Author.

Or, install Cog, a clean simple flac/shn gapless player
I found VLC somewhat weird and non intuitive to setup and use, especially when it comes to importing the libraries, so depending on your system and preferences, give Cog audio player a try. It's a very simple app, all you have to do is set the path to your music directory in the Cog preferences, then there's a small icon to the upper left of the left end of the track position slider, you click that and your collection pops out on the right, then you just drag over to the main window a folder with the audio files, or a single track, and it plays them.

Perfect if you have your collection all in one place. I didn't see any way to add locations though, so it seems it's all or nothing, so I guess if you use external disks to store your music, you might want to create a symbolic link to the collection in the main user music folder.

If you think Microsoft is bad about their decisions, Apple makes them look like virtual saints. If Microsoft tried doing anything like this they'd be in court for monopoly violations in a heartbeat.
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According to wikipedia, iTunes can currently read, write and convert between MP3, AIFF, WAV, MPEG-4, AAC and Apple Lossless (.m4a). That is we still cannot import and play FLAC in iTunes.

In order to play FLAC in iTunes, we had better convert FLAC to iTunes more supported audio format with a third party software like dbpoweramp, fluck, idealshare videogo.

I use iDealshare VideoGo which has both Mac and Windows to convert FLAC to Apple Lossless, MP3, WAV, AAC, AIFF. And it works very well.

Just google search How to Use iDealshare VideoGo to Convert FLAC to iTunes, you will find a detailed guide.

Resources: <removed blatant link drop, please don't insult our intelligence here, it's annoying. Also remember, are you sure you want to use software that does forum spamming to try to promote itself? Real world users, take note, use VLC, which does not need to do forum link spamming to promote itself since it's an actually good useful open source/free software project>
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Joined: 26 Sep 2003
Posts: 4122
Location: East Coast, West Coast? I know it's one of them.
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Even though this is obviously a link drop attempt, I'll leave the post up, but remove the link. Our forum explicitly states that no link drops are allowed, yet people always insist on trying anyway.

Toss out your itunes garbage and use vlc, then you don't have these problems, or, better yet, just dump apple and use stuff that supports free methods and codecs naturally, without contortions.
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