When comparing MediaMonkey vs iTunes, the Slant community recommends MediaMonkey for most people. In the question“What are the best audio players for Windows?” MediaMonkey is ranked 6th while iTunes is ranked 23rd. The most important reason people chose MediaMonkey is:
You can organize music by over 40 different criteria, including common criteria such as title, artist, and album, as well as items like track volume, lyricist, and parental rating. You can even use custom labels by which to organize and you can set how you want to prioritize the criteria. Media Monkey can also rename large batches of files based on set rules.
Specs
Ranked in these QuestionsQuestion Ranking
Pros
Pro Exceptional cataloging options
You can organize music by over 40 different criteria, including common criteria such as title, artist, and album, as well as items like track volume, lyricist, and parental rating. You can even use custom labels by which to organize and you can set how you want to prioritize the criteria. Media Monkey can also rename large batches of files based on set rules.
Pro Helps remove duplicates from the library
MediaMonkey can find duplicate files and songs, helping the user to remove any unnecessary items from the library.
Pro Can pull metadata from the web
Pro Works with almost any UPnP or DLNA enabled media player
MediaMonkey can stream the library to most UPnP or DLNA enabled devices. This allows you to, for example, stream to your Blu-Ray player.

Pro Powerful file renaming system
Pro Advanced automatic auto-dj
MediaMonkey has a built-in auto-dj feature, appropriately called Party Mode, that can automatically play tracks based on set criteria.
Pro Can convert audio and video files
MediaMonkey can convert all common audio formats and some video formats. Supported files include .mp3, .ogg, .aac, and .flac.
Pro Supports most tagging formats
Pro Format agnostic
MediaMonkey supports everything from lossy MP3 files to lossless FLAC files.
Pro Has a decent companion Android app which can sync with / connect to PC server
Pro Can build smart playlists with automatic filters
For example:
- 4+ stars jazz songs
- Top played recent songs
- Best rated classic rock
- Unplayed recently added songs
- Build your own "smart" radio station, etc.
Pro Can create a playlist based on rules
There is a feature included in iTunes called Smart Playlists that allows the user to create playlists based on criteria such as BPM, Genre, Artist, Album, Plays, Rating, etc.
Pro Can automatically create playlists based on a chosen song
There is a feature called Genius included in iTunes that allows the user to select a song and create a playlist based on that song. It will analyze the music library and choose songs similar in tone to the one chosen.
Pro Syncs across devices
Synchronization of playback information, podcast subscriptions, and settings is possible in iTunes. It can also automatically download purchases made on other devices.
Pro Airplay support
Streaming audio to all Airplay enabled devices within WiFi range is permitted by iTunes. It's also possible to select more than one device to play a song at the same time.
Pro Can auto-import CDs
The user can set up iTunes in such a way that media (from CDs) can be automatically imported once a CD is inserted. This also comes with customizable import settings (bitrate, codec). Additionally, iTunes can automatically fetch track names from the Internet.
Pro Built-in parental controls
iTunes parental controls can be used to deny access to certain parts of iTunes such as podcasts, internet radio, store, or shared libraries, as well as restricting access to media that has a certain rating or warnings.
Pro Can autopull information about songs
Track names and album artwork can be automatically obtained by iTunes.
Pro Sleek interface
The interface of iTunes presents a flat, clean design with playback controls at the top-left, search at the top-right, and a row of ways to categorize available media beneath that. It can also be minimized to take up much less space. The minimized interface is called the Mini Player and it can be set to display on top of all other windows. It's possible to show iTunes on top of all other windows when playing movies as well.
Pro iTunes store has a huge selection of media
The iTunes store offers a huge catalog of videos, songs, and podcasts.
Pro Advanced podcast management
Pro iCloud integration
Pro Internet radio
A music streaming service called Radio is available in iTunes. It creates stations based on chosen genres, songs, or artists and requires Apple ID for access.
Pro Ability to add RSS feeds
The ability to add RSS feeds in iTunes keeps the user informed of the latest web content.
Cons
Con Not really "multi-user" friendly
Example: If you have a family, not everyone has same tastes or star ratings. You CAN achieve a somewhat multi-user experience, but it's overly complex and clunky.
Con Really buggy at times
- Biggest annoyance: Often get database errors (data corruption?). Usually, you'll end up clicking "cancel" in some dumb cryptic error prompt and/or restart app.
- Android sync isn't a breeze.
- Multiple instances sometimes open up (due to unknown cause) can cause the corruption / database issues. You should backup often just in case.
Con Accuracy of automatically pulled meta data can be spotty
In cases where a song is a part of multiple albums, or there's a re-release with slight changes (such as track numbers, bonus songs, etc.), MediaMonkey can get confused and apply wrong titles to songs based on their track numbers. It then ends up mislabeling content that has already been labeled correctly. There's also no way to manually set what album to base the auto-tagging on in order to work around this.

Con Heavyweight
With each update, iTunes appears to get bigger and bigger, though adding little more value, especially for the user who just wants to listen to and organize music.
Con Unfortunately required to fully manage iPods
Con Buggy iTunes app
Immediately after the worldwide launch of Apple Music, a new version of iTunes was released (12.2). Many users have reported issues with this release, such as music lists getting mixed up, music having wrong metadata, etc.
Con Duplicates media files
Con Album organization can be fragmented
Songs purchased from the same album at different times will be added as separate albums.
Con Authorization limit
