MediaMonkey Gold

Thomas Boldt

Effectiveness: Lots of powerful media library management tools
Price: Starting from $24.95 USD for all 4.x upgrades
Ease of Use: User interface could be polished for better usability
Support: Emails for technical issues, forum for community support


For users who are looking for a powerful program to manage their large media libraries, MediaMonkey provides a comprehensive range of features that cover virtually any media situation imaginable. Whether you have a thousand files to manage or a hundred thousand, MediaMonkey can process and update all your files and then organize them automatically however you like.

Unfortunately, that degree of control comes with a trade-off in terms of user interface and ease of use. Basic tools are easily usable, but the more powerful features require a bit of time to learn. Once you see it whip a mess of media files into a coherently organized library, however, you’ll be happy that you took the time to learn its little tricks!

What I Like: Multi-format Media Player. Automatic Tag Editor. Automatic Library Organizer. Mobile Device Syncing (including iOS devices). Community-developed Feature Extensions. Skinnable Interface.

What I Don’t Like: Default Interface Could Be Much Better. Difficult to Learn.


What is MediaMonkey?

Is MediaMonkey free?

Is MediaMonkey safe to use?

Does MediaMonkey work on Mac?

Is MediaMonkey Gold worth it?

Is MediaMonkey better than iTunes?

Why Trust Me for This Review?

My name is Thomas Boldt, and I’ve been working with digital media on my home computers almost since the concept was invented. Downloading media files over a dial-up internet connection was a painfully slow process, but it was also what started my media collection.

Over the years since then, I’ve only grown my collection, which has given me a clear understanding of how the world of digital media has evolved. As part of my later training as a graphic designer, I spent a long time learning the ins and outs of user interface and experience design, which makes it easy for me to spot the differences between a well-designed program and one that needs some work.

MediaMonkey did not provide me with a free copy of their software in exchange for this review, and they have had no editorial input or control over the content. All the views expressed in this review are my own.

Also, it may be worth noting that we actually purchased the program on our own budget (receipt below) in order to conduct this review. That allowed me to access and test all premium features.

Detailed Review of MediaMonkey Gold

Note: First of all, I have to say that there’s more to this program than I can fit into the review. I’ve broken down the primary functions of the software into a few main sections, but there’s still more that this software can do.

Library Management

Initially, the interface looks a little bare. There’s very little in the way of helpful instructions in this software, which is one of the few things about it that needs to be improved. However, a tap of the ‘Insert’ button or a visit to the File menu gets you started importing media into your library.

For this review, I’ve separated out a segment of my personal media library for testing. I’ve been meaning to clean it up for quite a while – almost 20 years, in the case of some files – and I’ve just never gotten around to it.

The program supports an impressive range of files, from the extremely common but aging MP3 standard that kickstarted the digital music revolution to the audiophile’s favorite lossless format FLAC. All of my files are MP3s, but most are files that I ripped myself during the early 2000s, long before the days of online databases integrated into every program so there are large gaps in the tag data.

The import process went smoothly enough, and I was able to configure MediaMonkey to constantly monitor my Media folder for changes, but you can already see that poor lonely Rage Against the Machine MP3 that has lost the rest of its album in the first library screenshot. There are a few other issues that I’d like to clear up, including missing track numbers and other hassles that are a pain to fix manually.

I also added in a few audiobooks to test how well the program handled different audio types – you wouldn’t want to be playing your collection on shuffle only to suddenly be dropped into the middle of a book. While MediaMonkey supports audiobooks, the collection isn’t enabled by default.

After a bit of searching, I found that it’s possible to enable the collection separately – but not all of my audiobooks were tagged properly.

Interestingly, this section also allows you complete control over the way you segment your collections. For example, it would be possible for me to create a Chillout Music collection that played only music files tagged with the genre Downtempo or Trip-hop, a BPM of under 60 and play them all cross-faded.

Whenever I added new media to my general library, the custom collection would automatically update. The possibilities are only limited by the amount of configuration you’re willing to do, but it’s also only available in the Gold version of the software. This same degree of control can be used to generate playlists based on any criteria, but again only in the Gold version.

One of the most powerful tools in MediaMonkey Gold is the automatic organizer. It makes it possible to completely restructure your folder system based on the tag info that is associated with each file. Typically, they are organized around artist name and then album name, but you can separate them out into new folders based on almost any criteria you want.

In this example, I’ve configured it to restructure the library based on the year the music was released, but I could start with genre, speed, or any of the other taggable aspects of my media files.

This is something to be extremely careful with, in case you accidentally wind up making a giant mess of your folders. While you can always correct it again with the same tool, it will take a little while to process a large library with tens of thousands of files. This makes it extremely important to have all of your media files tagged properly, so it’s time to move on to my favorite feature of the program.

Automatic Tagging

This really is MediaMonkey’s best time-saving tool: intelligent automatic control over the tagging of your media files – at least, as long as it works properly. Because most of the library browsing features assume that your library is correctly tagged already, it can’t properly sort out which files are in need of tagging.

I could try updating them all at once, but that might be a bit ambitious and slow down my review process.

Since everything is correctly organized in my file system, however, I can search them out that way and see how well the program identifies the files. Here’s a version of Rage Against the Machine’s self-titled debut that I never got around to tagging with the album name or proper track numbers, which makes it frustrating to listen to since most players just default to alphabetical order when they have no other info to work from.

While this is a bit confusing at first, eventually it becomes clear that the yellow highlights showcase the changes that will be made to my files – and the program even went so far as to find me a copy of the album cover and download the lyrics (with the exception of track #5, apparently due to some licensing issue).

A single click on ‘Auto-Tag’ to confirm the changes, and a split second later everything has been updated with the proper album name and track numbers.

I’m quite pleased with this result, especially when you consider how long it would take me to do by hand – finding the correct tracklist, selecting each file, opening tag properties, adding the number, saving, repeat 8 times – all for a single album.

All of the other albums that I needed to correct worked just as smoothly, which will save me an uncountable amount of time processing my full media library.

Device Management

No modern media manager would be complete without the ability to work with your mobile devices, and MediaMonkey immediately recognized and functioned with both my Samsung Galaxy S7 (and its SD Card) and my aging Apple iPhone 4. Transferring files to my iPhone was as fast and easy as using iTunes, and was a refreshingly simple way to copy files to my S7.

I never use automatic syncing features because my library has always been larger than the available space on my mobile devices, but the option is there for those who prefer to work with smaller libraries.

Regardless, one of the most interesting Gold features can be found in the mobile device management section. When working with a media library on a computer, it’s a relatively simple thing to download additional codecs that expand your computer’s ability to play different file types – but it’s not so easy on a mobile device.

Instead, MediaMonkey offers you the ability to automatically convert files to a compatible format while transferring to your device. You can even change the sampling rate to reduce file size for media files like podcasts or audiobooks, since you don’t really need CD-quality audio for speech content.

This allows you to dramatically increase the amount of those files you can fit into the limited space available on your mobile devices, and is another feature that’s only available in the Gold edition.

Unfortunately, working with my Galaxy S7 was the only time I ever ran into a bug with MediaMonkey. I was worried that I had accidentally triggered a sync of my media libraries, and so I quickly unplugged it – but when I plugged it back in, the program refused to recognize it even though Windows did without issue.

Luckily, all I had to do was close the program and restart it, and everything was back in working order.

Media Player

All of this media management is extremely useful, but only once it’s combined with a solid media player. MediaMonkey has a well-designed player system that integrates with the rest of the library management tools, and can play any file that the rest of the software is capable of reading. It has all the equalizers, queuing tools and other playlist controls you’d expect from a great media player, and it has a few extras as well such as volume leveling, beat visualization and party mode.

If you’re fiercely territorial about keeping control of your music during parties, you can even password protect party mode in the options to stop anyone else from mucking around with your settings or even put it into total lockdown mode – though I do not recommend that, the best parties usually shift and change organically as they go on!

If you use your computer to play yourself to sleep at night, you can even enable a highly configurable sleep timer that’s only available in the Gold edition. It can even shut down the computer or put it to sleep once your preset time has elapsed!

The Reasons Behind My Ratings

Effectiveness: 5/5

The program really does do it all when it comes to media, and do it all quite well. As a media manager and player, it never had issues with any of my files. I’ve been looking for a solid iTunes replacement that offers the kind of power-user options that I require, and MediaMonkey is perfect solution to that problem.

If you need a feature that this software doesn’t provide built-in, it’s entirely possible that someone from the community has already written a free extension or script for the program to expand its capabilities.

Price: 4.5/5

Since version 4 already does everything that I want, there’s no need to go for the most expensive license, and $25 for such a powerful tool is a small price to pay. If you don’t need any of the more advanced features found in Gold, then the free version should be more than adequate and should really earn it a 5/5 for price.

Ease of Use: 3.5/5

This is one thing that MediaMonkey could really use some work on. Since it’s designed for power users who are willing to learn complex tools, it doesn’t really need to be filled with tutorials – but even power users can appreciate a well-designed user interface. The entire interface can be customized and re-skinned, but that doesn’t necessarily make the program easier to use – sometimes, quite the opposite.

Support: 4.5/5

The official website is a trove of useful support information, from a knowledge base with lots of articles to an active community forum of other users. You can also easily submit a support ticket to the developers of the software, and it’s quite easy to do – although the program is so well-coded that I never ran into a single bug.

MediaMonkey Gold Alternatives

Foobar2000 (Windows / iOS / Android, Free)

I never really liked Foobar, but I have friends who have been using it for years and swear by it. It actually makes MediaMonkey look like it’s a well-designed, easy-to-use program, but that may just be because whenever I saw it, the user interface had been completely customized. It offers decent media library management, but none of the advanced tagging and organization features that make MediaMonkey so useful.

MusicBee (Windows, Free)

MusicBee is probably the best competitor to MediaMonkey, but it also happens to be the one that I tried first and eventually moved on from. It has a highly customizable user interface and a more appealing layout than MediaMonkey, but its tagging and organization features are not as powerful. It also features some odd UI choices that are done to prioritize style over usability, which is almost never the right design decision.

You can also read our guide on the best iPhone management software for more options.


If you’re a power-user who knows exactly what they want and who is willing to spend some time learning how to accomplish it, MediaMonkey is the perfect solution that checks all the right boxes. It’s definitely not aimed at the general or casual user, although it provides a lot of the functionality found in simpler programs as well.

The automatic tagging feature alone is going to save me countless hours cleaning up my own media library’s gaps, and I’m looking forwards to having a properly organized collection for the first time in… well, since it began!

So, do you find this MediaMonkey review helpful? Leave a comment below.