I take my Sony Walkman with me all the time since I go to college. It is convenient to use and offers the best listening experience ever. It is so cool that I cannot love it more. Normally, I prefer to transfer my favorite music to my Walkman for enjoying. Regarding the iTunes music, it is a bit annoying as I have to remove DRM first and then transfer iTunes to Sony Walkman. Fortunately, I have found two amazing methods to do this job for me effortlessly. They will be introduced in this post to help you convert iTunes to Sony Walkman.

Part 1: What is Sony Walkman

As being told in Wikipedia, Walkman is a Sony brand trade name, originally used for portable audio cassette players from the late 1970s onwards. In later years, it has been used by Sony to market digital portable audio/video players, as well as a line of mobile phones introduced in 2005. The Sony Walkman was blue and silver which contained bulky buttons. It also included an extra audio jack so two people could listen at a time. Like many other devices, Sony Walkman does not support DRM protected files so DRM has to be removed before it can be transferred to Sony Walkman for playing.

As Apple music on iTunes is protected with DRM copyright, it can only be applied on Apple devices like iPhone, iPad, Mac etc. Regarding other media players and devices, DRM-ed files lose their compatibility and have to be converted to other format like FLAC in order to win back compatibility with other devices. In the following, two programs, namely Leawo Prof. DRM and Leawo Video Converter will be introduced to firstly remove DRM from Apple music and convert DRM-free iTunes music to FLAC afterwards.

Part 2: Method 1: Convert iTunes DRM Music/Video to Sony Walkman with Leawo Prof. DRM

Leawo Prof. DRM is highly recommended here as it is a professional and efficient program in terms of removing DRM from iTunes movies, TV shows, music, and even audiobooks. It is an all-in-one program suite for iTunes DRM removal, including three independent modules, namely video, music, and audiobooks, without letting users experience any inconvenience during program application. If you are going to convert iTunes to Sony Walkman using Leawo Prof. DRM, the below tutorial guide can be of much help to you.

Step 1: Download and install Leawo Prof. DRM

Click the below button to download and install the program to your PC.

Step 2: Add iTunes music to the program

Click the Add Files button on the toolbar to import your iTunes music to the program.


Step 3: Set a directory to save the converted file

On the bottom area, set a directory to save the file after DRM removal.


Step 4: Edit the file before DRM is removed

Click the editing icon next to the file, and set parameters like channel, sampling rate, and bit rate for the file.


Step 5: Remove DRM and convert the file to mp3 format afterwards

Click the Convert button to remove DRM first from the file and then convert it to mp3 afterwards.


Note: Trust the PC/b>

Enter your Apple ID and password to trust the computer if you are prompted a window to do so.


Step 6: Check the converted file

Check for the converted file on the Converted tab after DRM is removed successfully. Note that now you can freely transfer iTunes music to Sony Walkman for playing iTunes music on Sony Walkman.


Part 3: Method 2: Convert iTunes to Sony Walkman with Requiem

Requiem is a good DRM removal program for iTunes movies and music. It is a program that removes Apple's DRM (called FairPlay) from songs, videos, and books purchased on iTunes, this allows content purchased on iTunes to be played on non-Apple-approved devices. The DRM removal is a lossless process, it is merely decrypting the file, not decoding and re-encoding it, meaning no quality is lost when the DRM is removed. Follow below steps to remove DRM from iTunes music using this program.

Step 1: Download latest Requiem 4.1.

Step 2: Run Requiem: Double-click on the Requiem application to launch it on your computer. It will automatically find DRM-ed files in your iTunes library. You can also drag & drop files or directories (which will be searched recursively) onto the Requiem application or the Requiem window. Starting Requiem with the shift key down will disable scanning of the iTunes library.


Step 3: Remove DRM: Then Requiem will remove the DRM of iTunes content automatically. The original DRMed files will be moved to the trash. Make sure you verify that the songs and videos still work before emptying the trash. After DRM is removed successfully, you can transfer iTunes music to Sony Walkman immediately.


Part 4: Comparison between Leawo Prof. DRM and Requiem

To play iTunes music on Sony Walkman, both the above mentioned iTunes to Sony Walkman converters are capable of removing DRM from iTunes music and convert it to the Sony Walkman compatible format. To better compare these two programs, a chart is given below to show their advantages and disadvantages clearly.

iTunes to Sony Walkman converters Leawo Prof. DRM Requiem
  • Provides professional DRM removal services
  • Supports a full range of media sources, namely iTunes video, music, and audiobook
  • Removes DRM at 6X speed
  • Offers 1:1 quality assurance as original files
  • Provides rich editing features
  • Supports both Windows and Mac
  • Provides up to 12 languages
  • Ensures 100% retaining of output file quality
  • Simple user interface
  • Freeware
  • Offers efficient DRM removal service
  • Ensures lossless output file quality
  • Requires software installation
  • Does not support iTunes 11 or above
  • Requires software installation

All in all, Leawo Prof. DRM is much more competent than Requiem in terms of working speed, media source supporting, and editing features. Therefore, if you are seeking methods to play iTunes music on Sony Walkman, install Leawo Prof. DRM and transfer iTunes to Sony Walkman within a few clicks.