I would recommend you check out this full DRM removal software review in the first place:

http://www.softdiggs.com/reviews/drm-removal-review.php
References :

http://files.uberdownloads.com/apps/lps/index.php?product=mediacoder

This one is the best I’ve found that’s free (I own several that aren’t). What you need to do is quite simple, and I’ll even give you a step by step guide!

1. Download the software from that link
2. Install it.
3. Take all the music you want onto your phone and add it to the list of songs to convert
4. Convert all those songs TO MP3 FORMAT. This is a format that talk to Windows Media Player
5. Before converting, make sure you know where your music is being sent after conversion.
6. Your new mp3’s will be Windows Media Player usable and you can put whatever you want on your phone.

Now, from a computer junkie to you, I would convert every single music file you own. Why? Because mp3 is a universal music format. Everything can play an mp3. iPods, Zunes, Phones, Gaming Consoles, DVD players, anything. If it’s in mp3 format, you’ll never have to worry about having to post a question like this again.

However, if they are in mp3 and you don’t need to convert them do this instead:
1. Open Windows Media Player
2. Click the "Organize" tab if it’s the newest one, "Libraries" if it’s older.
3. Click manage libraries.
4. You’ll see a list of folders, click "add" then find the folder with your music in it. Add it.
5. Hit okay.

This is the "official" version of how to add music to your Windows Media Player list. As soon as you add the new folder, Windows Media Player will automatically search for, and add, everything in your music folder.

Hopes this helps, merry christmas!
References :
I’m that guy who didn’t get laid until college.

It can automatically transfer your iPod and iPhone music, video, playlist, photos back to PC and iTunes. Backup all your music and video in a couple of clicks. If you own more than one iPods, it can simultaneously manage all the iPods in the same interface, you may transfer files among these iPods by drag-and-drop.

http://www.dvd-video-tool.com/ipod-transfer.html
References :

With it you can:
1: Transfer iPod files to Computer
2: Transfer iPod files to new iPod
3: Transfer iPod files to iTunes
4?Transfer local files to iPod without iTunes
5: Manage your iPod like a movable hard drive and transfer ipod videos/photos/music between iPod and iPod, iPod and computer/laptop, ipod and itunes.

You can find it here:

http://www.topmediasoft.com/ipod-transfer-avcware.html

It is easy to use and you can try it now.
References :

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Key Function:
1: Transfer/Share iPod files from one iPod to another iPod.
2: Transfer/Backup iPod files from iPod to your computer.
3: Transfer/Backup iPod files from iPod to your iTunes.
4: Manage your iPod like an harddisk.

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References :