Best iPod-compatible iTunes alternatives

For better or worse, buying an iPod also means committing to Apple's iTunes software. Apple's seamless combination of hardware, software and online store has made it many fans, but for some folks, the iTunes way of doing things feels unbearably confining.

If you love your iPod, but can't stand being tied to iTunes, there are some compelling and capable Mac and PC iTunes alternatives that can sync with your iPod. Depending on your iPod model, you'll probably still need to keep iTunes around for firmware updates, video purchases, games and some advanced features (calendar syncing, for instance), but there's no reason you can't sync your music and podcasts using a different program.

Each of the following media jukeboxes has its own set of advantages and disadvantages. This list isn't meant to be comprehensive (by all means, add your own suggestions in the comments section), we're just taking an opportunity to highlight some personal favourites. Also, every application listed here is free, so there's no reason not to try them all and see what sticks.

Media Monkey is a control freak's dream come true.

Media Monkey

Ideal user: File hoarders, control freaks, meticulous taggers, boutique format users (FLAC, Ogg), people with messy collections.

  • Pros
  • Ideal for large, scattered collections
  • Advanced tagging features and auto tagging
  • Supports iPhone 3G and iPod Touch 2G
  • Copy songs from iPod to computer
  • Album art lookup
  • Skinnable
  • Podcast catcher
  • Plug-ins
  • Generate HTML reports
  • Cons
  • Overwhelming for nontech users
  • Doesn't manage videos
  • No Mac version
  • Folder monitoring requires upgrade to Gold (US$20)

Like Floola, SharePod launches directly from your iPod and offers utilitarian control over managing and backing up your iPod's tunes.


Ideal user: Anyone lacking administrative rights on a work or loaner computer who wants a basic way to manage and backup their iPod without installing an application.

  • Pros
  • Launches directly from your iPod
  • iPhone and iPod Touch compatibility
  • Copy songs from iPod to computer
  • Advanced tagging capabilities
  • Basic video management
  • Exports iPod contents to iTunes (including ratings and playlists)
  • Drag-and-drop operation
  • Friendly GUI for the technologically timid
  • Backs up and restores your entire iPod
  • Cons
  • Windows only
  • No podcast management
  • No CD ripping or burning
  • No photo import
  • Too basic for demanding users

Ten years of development has made Winamp an impressive iTunes adversary.


Ideal user: Perfect for people who crave lots of features and flexibility from their jukebox. Especially good for Internet radio fans.

  • Pros
  • Tons of integrated streaming radio channels (shoutCast, AOL, CBS)
  • Multiple folder monitoring
  • Flash video support
  • Multiple language support
  • Auto-tagging function for cleaning up your music collection
  • Ability to stream music collection remotely
  • Skins and plug-ins
  • Copies media from iPod to computer
  • Visualiser
  • Built-in Web browser
  • Podcast lookup and catcher
  • Song recommendations
  • Album art lookup
  • Cons
  • You'll need to upgrade to Winamp Pro (US$20) for speedy and flexible ripping, burning and encoding
  • Overwhelming layout (not everyone wants to fiddle with skins)
  • Deep features may confuse some users
  • No photo management
  • No Mac version

Songbird's clean interface integrates free music downloads from around the Web, as well as local concert listings.


Ideal user: Music addicts, hipsters, concertgoers, file hoarders, people who often jump between Mac and PC.

  • Pros
  • Mac/PC compatible
  • Free music downloads integrated and continually refreshed from Hype Machine
  • Attractive GUI (also skinnable)
  • Plug-in support (Flickr,, Lyrics, etc.)
  • Integrated Shoutcast Internet radio
  • Built-in Web browser
  • Concert listings
  • Attractive GUI
  • Cons
  • No multifolder monitor, yet (February '09)
  • No CD ripping or burning
  • No video or photo management
  • Doesn't support iPhone, Touch or 4G Nano
  • No Podcasts

Floola launches directly from your iPod and works with Mac, PC and Linux.


Ideal user: Nomads, the Internet cafe crowd, anyone working on a computer without admin rights for installing applications.

  • Pros
  • Mac/PC/Linux compatible
  • Launches from iPod
  • Manages videos, photos
  • Converts videos from Web
  • Copy songs from iPod to computer
  • scrobble support
  • Converts music formats on the fly
  • Drag and drop operation
  • Podcast catcher with auto-delete management
  • Multifolder synchronisation
  • Cons
  • Doesn't support latest iPod Touch or iPhone
  • Not the prettiest thing to look at
  • No CD ripping or burning
  • Solicits donations every time you close the application

Add Your Comment 15

Post comment as

hermero posted a comment   

iTunes is upsetting....Little troubleshooting support, on top.
I have an i-Pod Classic and only
want to import my music from the Windows library ( sync ).
Like all the albums neatlytagged with songs well identified. Will
greatly appreciate recomms from you, my friends. Tks.


sginthehouse posted a comment   

Hiya! am music sick. would download the entire world but cannot put all my music on my ipod as i download music from music site (such as bearshare), which are not supported by itunes.So, have to copy everything on CD AND save it on itunes then. Anybody has a better idea?? Many thanks! take care


elbravo posted a reply   

hey there I got your message, well I'm gonna tell ya what I actually use to get music and video into my ipod without pay anything at all but it's takes a little while but you'll get used to it. anyway here I go.

the program for video it's call,
total video converter(it basically a software that allow you to convert any kind of format to Mp4 etc for your ipod, xbox moval phone and more)
use that software to convert any video you wants except RM(real media) you can even convert music but I woud'nt use it because sometimes doesnt work.

for music use video MP3 extractor (software use to converte any kind of video to a mp3 and more there's another one but i dn thave the name right now cos i've just format my laptop but I'll let you know when I got it back, meantime that's all you need.


elbravo posted a comment   

you know guys all of you are silly I dont use any of those programs i can manage to introduce any video or music on my ipod whitout paying anything at all free free Ive got 200 song and 15 videos(from everywhere) if anyone is interesting on this send me an email
to send you the programs(only names)


Durham posted a reply   

Wow a whole 200 songs, that kind of destroys my collection of 100,000 songs.


Killerfoe posted a reply   

100,000?.. excuse me while i laugh..


Killerfoe posted a reply   

100,000?.. excuse me while i laugh..


Manny Munster posted a comment   

My Choice is MediaMonkey V 3.2 and plus. Is not the best software of the world, but is able to manage music better than iTunes


klas posted a comment   

Media Monkey is the best program i ever had


DW posted a comment   

Floola is the easiest to use/quickest for an itunes alternative. Since I switched from Itunes to Floola like a year ago, I've never gone back.


TallicadaZ posted a comment   

great review, thanks

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