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Ben Nadel at CFUNITED 2009 (Lansdowne, VA) with: Garrett Johnson
Ben Nadel at CFUNITED 2009 (Lansdowne, VA) with: Garrett Johnson ( @gjohnson391 )

Attempting Switch To iTunes From WinAmp

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I have been a long time WinAmp user. I love WinAmp; it does just about anything that I want, including downloading album art and mostly integrating with my all my iPods, including my new 160 gig iPod Classic. As of late, though, I have wanted to get more into audio books, so I thought I would try out iTunes again to take advantage of the whole iTunes Store integration where I would be able to easily purchase and download audio books.

I have resisted moving to iTunes for a long time because WinAmp has been so incredible. But, this morning, I gave it a go, and I have to say that I am really frustrated with it. Here's what I'm not liking about it, so someone please tell me if I can fix this:

ONE. My number one issue with iTunes, and this really feels like a deal breaker, is that the media keys on my keyboard no longer work. No pause, no play, no skip to next song. I have searched high and low through all the menus and preferences and I cannot seem to find a way to add hotkey hooks to the iTunes functionality. To be honest, if someone cannot recommend a way to do this, I simply can't use iTunes. At work, music is a background experience and when I hear something I don't like, I move my finger an inch up and hit the Next Track button on my keyboard. If I have to switch to iTunes to actually change the song... absolutely not.

TWO. I don't care about Album art. But, nevertheless, I do think it looks pretty and people always boast about how iTunes will download album art for you. So, I gave it a try. When I clicked on Download Album Art, iTunes alerted me that I needed an iTunes account in order to download the artwork. Are you serious?!? You're telling me, I need special permission to download album art? Are you telling me that WinAmp and Windows Media Player (and I am sure many other players) can do this hassle-free, but in iTunes, I need an account to download the artwork?!?

Ok fine! Let me sign up for an account. But where? To sign up, I did what I thought was the most natural thing when signing up for an account - I went to Right? I mean, to sign up for a Fandango account, I go to; to sign up for a Blockbuster account, I go to; that is the general paradigm of web site integration. Well, when I get to, I am redirected to No problem, I click on iPod+iTunes.

Now what? I can't find any links to "Login", "Account", or "Sign up". I search in vain for something that has anything to do with an account. Nothing. Finally, I figure clicking on the "Redeem iTunes Gift Card" link cause I think, ok maybe that will ask me about my account information (inevitably with a "sign up" link if I don't have one yet). Well, when I click on it, I get a friendly alert from my browser telling me that "An external application must be launched to handle this request" and that if this was not expected, "this request might be an attempt to exploit a weakness".

My iTunes application is ALREADY opened, so I can only assume something has seriously gone wrong?!? After about 10 more minutes of searching in vain, I decide to go back to my iTunes app and start poking around. On the left, I come across the iTunes Store link. I figure this might offer some hope.... but, again, nothing. All I see is a ton of links to albums and movies. No Create New Account. No login. Oh wait, there it is - a tiny little button OUTSIDE the content area at the way top-right of the screen (but at least its a small gray button that blends with the chrome background).

Ok, so I finally get to the Create New Account page. I start entering out the email and password information. I am already irritated that iTunes (just like the Mac's default settings) doesn't TAB to the drop down boxes. What is up with that? Why such a big fear of tabbing? But that's not my biggest problem; on the next screen, I have to enter my credit card information. Are you SERIOUS!?!?!??! I just want to download some album art and you're telling me that in order to do that you need to credit card information?!?!?

Needless to say, I didn't give that info and now, apparently, I cannot download album art.

THREE. The music buttons in iTunes don't respond unless the iTunes application is "in focus". The way I have my computer set up is that I have two monitors - the primary one in front of me, and an auxiliary one to the side. The auxiliary one basically IS my music player. I have iTunes open there. The problem is, it's rarely in focus since I am always in another application, like FireFox or Homesite. So, use case scenario, I hear a song I don't like and, since my keyboard doesn't work anymore, I mouse over to iTunes on the second monitor and click the next track button... nothing happens. I click again, and it works, now that iTunes is the "current" application. Great, so not only do my media keys NOT work, now I have to click TWICE to switch songs!!

FOUR. Network music? With WinAmp, there is a very clear and powerful separation between the "Media Library" and the "Playlist". As such, I could add shared files to my play list without messing up my core library. For example, one of the guys at the office has a Christmas Songs folder shared from his local computer. How can I play that such that it won't mess up my media library in iTunes? I can't seem to figure this, out, but I assume there is a way, since this seems like such an obvious use-case.

FIVE. This is minor, but the scrolling in the media library just feels very unresponsive. There seems to be a highly noticeable lag between where my mouse is on the scroll bar and what scrolling is actually taking place.

Ok, that's about it. I am gonna give iTunes the full day of use. I don't want to jump to any conclusions, and if someone out there can PLEASE tell me how to get my media keys to work from the keyboard, I would gladly bear your first born. But, I have to say that my initial experience has not been a pleasant one.

Note: I am running late, so I did not proof read this.

Reader Comments


Not a complete solution, but FoxyTunes can interact and control iTunes, which will help with some of your points.

Of course, being a web developer, I assume you use FireFox and spend the majority of your day staring at a web browser. :)


It's interesting how relatively small things can lead someone to love or hate a program. Maybe it's because so many programs do what itunes and winamp can do (basically play music) that the small things start to matter more.

Anyway, in response to number 4, i think itunes only plays well with network music shared throught itunes. Then it will come up as a network library, much like you describe in winamp, pretty sure that this is the only easy way to do it.

Also you have to remember, iTunes is the front end of a shop in reality, and therefore requires a certain amount of 'loyalty'.

hope you get on better with it over time, if not just use it for audio books, and keep winamp for the music :)



I will take a look at MediaMonkey - the screen shots look pretty cool.


You're damn right that I stare at FireFox all day ;) I will take a look at FoxyTunes.


I think you raise the best point, that iTunes is the front to a store. Yes, it is a media player to a certain extent, but really, when it comes to media functionality, it falls a bit short. I think the way it is marketing is a bit misleading. But, perhaps that is all part of the marketing strategy... or maybe that is just what the "iLife" is.


One easy way to add album art is to select all of the songs in the album and then right click and select Get Info. A Window will pop up and over tot he right in the middle will be a box for album art. What i usually do if iTunes can't find any artwork for some of my albums I'll search for the cover art in google images or amazon's music store. I try to find a high res photo that is square. All you need to do is drag that image from the browser straight to that drop box and you've got album art.


As far as clicking on links in the web browser that cause pop ups to occur when trying to open iTunes, it doesn't matter if iTunes is open or not, this message is mostly a warning that something on the internet is communicating with an application on your computer. The reason it pops up even when your iTunes is open is because simply, the web application doesn't know that it's already open, all it's concerned about is getting the message delivered to the application to open or start, in fact i think if it's already open iTunes will navigate to the link that is being passed, like an artist's page in the music store or something. You haven't done anything wrong nor is anything going wrong, it's just a necessary step to let you know what's going on. I say give it some time... iTunes holds alot underneath it's hood that you won't find right away. You don't have anything to lose but you have a lot to gain!


Hey Ben, Sorry for the many comments. I thought of one more. I suggest using Quicksilver ( for controlling iTunes with Hot Keys. This will definitely be using Quicksilver's most basic task but it will atleast introduce you to life with Quicksilver and at the same time fix your iTunes dilema. Alright, I think I'm done!


Lehi, I think QuickSilver is a Mac only deal and I think Ben is on a PC.

Ben, you seem to have enough obstacle that you'd probably be better off with WinAmp for your purposes. Use iTunes simply to download the audio books you want, then import them into WinAmp.

I use iTunes only for the management of my music, iPod synching, and occasional purchases. I decided to keep my work computer free of music and games, etc., so I use my iPod in an iHome player (also has AM/FM). I prefer to not use extra computer resources just to play music. But this is just me.

Good luck with it all...



Thanks for the comments (no need to be sorry for educating me!). I tried the album art thing, but the Get Info didn't seem to do the trick. My iTunes version is pretty new (I think), so maybe its something they got rid of (or maybe its too old).

I will look into this Quick Silver thing. Not sure if I am considered a "power user" on a computer, but certainly, I am always looking for ways to make the keyboard a more effective tool. Going to the mouse does nothing but give me repetitive stress issues :)


Todays update....

I answer the phones a lot at work (I like that kind of hands-on touch with the clients) and as part of that, I have to answer a main line that rings for everyone. When I do this, habitually, I would move my hand to the phone, and on the way, I would hit pause on my keyboard. Now, when I answer the phones, I have to answer the phone with one hand while simultaneously trying to "focus" my iTunes and click the Pause button with my other hand.

I know that my situation might be somewhat unique, but certainly, having to coordinate both hands is becoming a little irritable.

Along the same lines, if someone calls me across the room, traditionally, I would just hit the pause button on my keyboard and roll around in my chair. Now, the act of pausing just has a relatively large amount of overhead to it.

I am still gonna give it the full day of use, but this hotkey issue is becoming a deal breaker for the way I interact with my work environment.


Slightly in regards to the network music comment. All the itunes users in the office will "see" each other in the interface (provided you have it turned on) and you don't have to mingle each other's libraries together at all.


Time to get an office standard. ;)

My only complaint about itunes is that it's a pig and at work, where I don't use an iPod, I have to install their silly device drivers / services in the extreme case that I would ever want to plug an ipod in (which, I'll never do at work). Plug-n-play is cool and all, but sometimes it's overkill.


+1 for MediaMonkey on Windows.

I gave up iTunes when at some point it deleted/rearranged a load of stuff - I think I was playing with the find duplicates function or something. Anyway - it totally butchered my existing file organization.


Ben, I don't have much to offer in the way of tips/suggestions, but I second all of the issues you have raised. It seems you and I have a very similar setup (dual monitor, firefox, CF Studio) and I'm a long-time Winamp user. I tried and tried to switch to iTunes when I got my first iPod 3 years ago, and while it was a pretty app, it was an absolute pig, and limited me in many ways as you've described. For me, the hotkey thing was the dealbreaker as well. I have all of my Winamp hotkeys mapped to the number pad and I can skip tracks, volume up/down, pause/play, bring Winamp into focus with a single stroke and without ever leaving the keyboard. Funny, because it's the same reason I can't, for the life of me, abandon CF Studio. The custom hotkeys mapped to snippets are invaluable. I end up being able to code very effectively (while listening to music, and still interacting with the world around me) without much need for a mouse.

Anyway, I've done as Matt described above. I open iTunes only when I get new music (CD or digital download) to organize the actual files and get them synced to my iPod. I know I could do that other ways, but that is one thing iTunes makes very easy...which, I believe, is the reason so many people swear by it. If you've never used anything else, it's really easy to use, to organize your library and you don't know what you're missing in other tools.



With WinAmp, I use the ml iPod plugin:

It seems to have a lot of the features that iTunes supports. And, on top of that, I can add music TO my iPod directly from my playlist which may have songs that not even in my media library. So, often times, I will drag something from my desktop onto my playlist, then right click and Send To - iPod.

It looks like it has a lot of other goodness, but I have not taken the time to explore it yet.

But, I agree, hotkeys with any app are super important. One thing that Mac does (to a certain extent) is not just make something user friendly, but ALSO seems to limit the power of more advanced users. I find this especially true of the ALT-TAB functionality; in Windows, this will go between all open instances of an app; in Mac, this will only switch between applications. So, if I have 4 FireFox windows open, in Windows, easily switch back and forth; in Mac, not so easy :(

Don't hate on advanced features :(


@Jeff, you're aware that both Dreamweaver CS3 and CFeclipse has snipplets and such, right? o_O - I confess, I understand that CFStudio had some pretty cool snipplet management and stuff. Only thing that annoys me about DWCS3 is that I can't just make cntrl+alt+c my "comment" snipplet, but I've since changed that to cntrl+shift+c and it works well enough.

CFeclipse's snipplet management is a cross between Lifehacker's Texter ( ) application and the old snipplet command style.


Don't buy audio books from iTunes. I believe that Apple made an arrangement with Audible to provide the book sales. If you sign up with, they have a monthly plan where you essentially get 1 book a month from around $15.00 and able to buy the rest at a considerable discount. The iPod is supported as well as other players, and purchases made directly through audible will load into iTunes.

The audible book format (AA) is proprietary, but I've been very happy with their service. They have a nice selection of unabridged volumes, though you may miss a couple of major titles (i.e. Harry Potter series)



I was actually looking through last night. It looks like a cool service, but their site seemed very difficult to find information about the plans. FOr example, if I do the bottom plan and get one book a month, what happens if I want a second book? Can I buy extra credits? Do I pay normal price? Is it still discounted?

I couldn't find any of these answers online.


@Todd, yes I'm aware of those capabilities. To be clear, it's not the snippets that are lacking in these apps, it's the ability to assign ANY hotkey combination to ANY snippet, without needing to first type in some snippet code or abbreviation. I want ctrl+shift+l to insert a single line comment, and ctrl+shift+8 to insert a javascript multi-line comment, etc. It's that flexibility (which is very similar to Winamp global hotkeys) that make the app extremely customizable to my unique work style.

And FWIW, I've tried a DW demo three times and it always feels to me like CF Studio on steroids...including the unnatural body hair and anger management issues. Eclipse (or maybe it's CFEclipse) is still too buggy for my use. That's not intended to start a holy's just my opinion. There are a few key bugs that have been around for quite some time, that have royally screwed up my code before and are show-stoppers.


Give up on it man... Itunes just sucks so bad it's not even worth attempting to use it again...

Just wait till you get the next update request in a couple of weeks and need to download the whole program again, and the Quick Time icon magically shows up again in yout task bar.

Even better, you gotta go into control panel preferences and open the quick time preferences just to change the sound source from headphones to speakers.

You would think play online radio stream is under file but no It's under Advanced menu...

The one positive is the search button. I have about 7000 songs and that helps a bit, but then you need to clear the search if you just wanted to find a quick song to play and then go back to the playlist.

I use Itunes for one reason and that only... FinalScratch which I use for DJing needs that to sink in new songs and playlists with the Itunes music folder.

Out side of that, I get mp3s from so the applestore can kiss my $#%


I have a Windows ergo keyboard with media keys. I never use them :)

I'm wondering now though if they can be mapped with AutoHotKey. That might be useful!



I've never heard of before, but I've been going through it this morning and it is an awesome site! I've been on it for about 15 minutes and here's what I love about it:

1. I can bookmark artists / labels to my account.

2. The previews really give you a good chunk of the song (like a minute or two) so you can really get a sense of what the song is like.

3. Easy genre navigation.

4. Good suggestions based on current selection.

Anyway, thanks for pointing this site out. I think I am really going to like it.


I use for my audiobooks. I import then into iTunes. You could import this into WinAmp.

I use iTunes but I do like WinAmp.

iTunes gripes...I personally would like to have more control over my file organization. Duplicates from my previous library, file name screw ups and other crap in my archive (built since 1998) creates a special amount of misery for me.

On is one audiobook I highly recommend. Hitchhiker's Guide to the Galaxy (read by Stephen Fry). Possibly the best fiction audiobook in my collection.

As far as iTunes goes. I am happy with it but I was a bit more excited about it than most people were when it came out.


*WAY* out of date response, but I thought I'd add this.

I gave my Dad an iPod Shuffle for Christmas and while setting things up for him, I used iTunes for the first time. I found the Music Library management interface far superior to WinAmp, the application as a whole far less system-intensive, and since I can control iTunes from FireFox accessibility isn't a problem. The Album Art thing doesn't bother me, because I can grab album art from the web and add it myself. CD ripping is very convenient (Dad had 4 CD's ripped by the time he got tired of playing with it). ID3 tagging seems easier, too.

In essence, everything that annoys me about WinAmp is vastly improved in iTunes. Sorry, WinAmp- it's the Uninstall Bin for you.



I actually have iTunes open right now because I was buying an audio book. I am gonna leave it open for a while, give it another go.


I just had the same problem with the media keys working with iTunes on my new Saitek Eclipse II keyboard, but I found a solution. Apparently it also works with the G15 keyboard, as well as most others with media keys. I am currently using this with the lastest version of iTunes, 7.6.

Go to this forum topic, and download the file in the first post (you must register before you can download).
It's a simple dll file that you drop into your itunes plug-ins directory. If you are using XP or earlier, put it in C:\Program Files\iTunes\Plug-Ins

If you are using Vista, install it here: C:\Users\<username>\AppData\Roaming\Apple Computer\iTunes\iTunes Plug-ins


Ben i have the exact problem with the keyboard hotkeys that you are facing. If you find a solution id appreciate if you could send me an email.


Hey I found a program for hotkeys ( It works for windows, and it allows for itunes to be minimized while still allowing me to use my keyboard media keys. It's actually pretty cool, check it out.


iTunes sucks. I just use it for iPhone apps.

I think Jobs has much much to learn from winamp.

Like every other software that apple created iTunes is also a crap

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