In Which Spotify Leads Me to iTunes Home Sharing

The story of how iTunes and Spotify co-exist as a near-perfect music listening environment.

itunes + spotify = happy music

So I was recently sent an invitation to join the “exclusive” ranks of American Spotify users. I had been hearing about the free all-you-can-stream music service for quite some time, but never gave it much serious thought. Maybe it was my years being stranded in a slow-Internet hell, but I’ve never held streaming services is especially high regard. Besides, with a music library as large as mine, I am usually hard-pressed to find many songs that I want to listen to at any given moment that are not already stored in iTunes. And I’ve invested so much effort into that little jukebox that, at the press of a button, I could literally listen to music for 55 days straight and never hear the same song twice.

Despite that, I signed up for Spotify anyway, just to see what all the fuss was about. My initial impression is that the rave reviews are justified. The program is simple to use: search for song->press play. And though the collection of available songs is quite extensive, it is not quite up to the bold marketing claim of “every song ever”. There have been a handful of (admittedly obscure) tracks and artists that I’ve been disappointed not to find.

Rarities aside, if you want to hear it, you can find it. Around here, Spotify has quickly replaced YouTube as the go-to source for one-off indulgences or for finding songs that come up in discussions but aren’t in my iTunes library.

The real power of Spotify is in its immediacy. Virtually any song can be found in a matter of seconds, which makes it a superb platform for exploration. I no longer have to buy or bootleg an album just to see if I’ll like it. I can listen to it in its entirety as many times as I want. And I’ve already spent a considerable amount of time cruising the full catalogs of artists I hadn’t thought about in a while. I had no idea PJ Harvey had so many albums.

A lot of deep cuts, b-sides and compilation appearances are also available. So if you like to dig into the music of your favorite artists, Spotify is a great way to do so. All-in-all, a big thumbs up for Spotify from me. I can see myself getting a lot of use from the service in the future.

A few other observations:

  • Albums often have the wrong year associated with them. Nine Inch Nail’s Head Like A Hole single/EP was released in 1990, not 2011. And there are plenty more examples where the date is more recent than it should be. So many so, I don’t trust the dates until I’ve seen them confirmed by an outside source. I don’t know where Spotify gets its data from, but this needs to be fixed.
  • Tricksy Spotify pauses commercials if you mute the computer, so there’s no avoiding them.
  • However, songs are not paused if the computer is muted. This is disappointing, especially after seeing the behavior with the ads.
  • The ads themselves cover the usual self-promotion gamut (encouraging the exploration of Spotify’s full range of services), as well as promotions for new content (artists, albums, etc). I don’t mind the promos, but the content ads can be a little jarring. It’s quite disconcerting to have your mellow Yo La Tengo marathon interrupted by boisterous ads for Thug Rapper Whozit or Popstar Whatserface. If the ads were more relevant to my interests (say, based on my listening habits), I wouldn’t really mind them. But as it stands I just find them annoying. Neither the artist nor record companies nor I receive any benefit from having Top 40 content directed at me.

So what does all this have to do with iTunes?

The thing is, I like Spotify. And I can see how it has the potential to be a massive disruptive influence on people’s music listening habits. The murder-obsessed tech media has been calling it “an iTunes killer” for some time, even before it was available in the States.

And it certainly had an effect here; it made me realize how much I missed being able to listen to music at my computer. Crazy thought isn’t it? I love music, but for the longest time, technological limitation has made it difficult for me to listen to it in the places I most often am.

Since the day iTunes came out, my library has been too large to fit on the internal drives of any computer I’ve ever owned. As drives got bigger, so did my library. Thus the library has been forced to live on an external drive connected to my iMac for its entire existence.

I, however, rarely do any actual work on my iMac. I’m more frequently found using a laptop from the comfort of a couch, bed or dining table. These days, the iMac mostly acts as a server and information hub/data manager.

My library is a rather complicated thing. The shear size of it necessitates a rigorous organizational structure (taking full advantage of multiple smart playlists based on play counts, play dates, star ratings, etc) to be used effectively. And traditionally, the problem has been that it’s hard to listen to music in places other than the iMac without corrupting the integrity of the library.

This effectively meant that my music library was isolated from the other computers in the house. All my vast quantities of tunes inaccessible save for some workarounds of various success:

  • Grabbing files over the network directly and/or using a third-party music player program. Advantage: playing music from the laptop itself. Disadvantages: no interaction with the library.
  • An iPod. Advantage: Since iPods are extensions of the iTunes library, I didn’t have to worry about breaking my organization. Disadvantage: requires headphones, limited music selections, metadata/playlists only updated at sync time.
  • iTunes Sharing/LAN streaming. Advantage: Access to the full library from any computer in the house. Disadvantage: does not update song metadata, so I could listen to songs, but my playlists would not get updated or refreshed.
  • Airfoil, essentially pushing music from the iMac to other computers. Advantages: music is sourced from the main library and can be played simultaneously on multiple computers. Disadvantages: cumbersome to set up, difficult to control.

This is the environment I was operating in when I discovered Spotify. Not a group of ideal solutions there.

Spotify’s ease of use reminded me that I wanted to easily play my music on a laptop. But as much as I like Spotify, using it exclusively is out of the question. For one, there are songs in my library that aren’t on Spotify. It also doesn’t share/sync local files (that aren’t in its database) between computers, so the app wouldn’t actually solve my multi-Mac music dilemma. Ultimately though, what’s the point of having a meticulously maintained, tagged and organized music collection sitting in the next room if I’m just going to stream it all over the Internet? Besides, there’s no guarantee on Spotify’s lifespan; its service could change or be shutdown completely in the future. My local library will remain usable even if Apple goes out of business tomorrow.

Also, no smart playlists. And I loves me some smart playlists.

While Spotify isn’t a solution for me, it did inspire me to look for others. My first inclination was to look at iTunes LAN streaming, which allows the client laptop to access and control the music. I’d seen some solutions to the metadata problem in the past, but none of them ever worked for me. I hoped that there had been more recent developments.

Enter Home Sharing

Fortunately, one of the first search results I found pointed out the oft-overlooked preference in iTunes to allow Home Sharing to update play counts. Until this point, I had never considered Home Sharing. When Apple introduced the feature in iTunes 9 two years ago, it was pitched as a way for family members to share music among their computers. Since I’m only one guy, I didn’t think, like parental controls, that the feature would be of much use to me.

So I ignored it.

My mistake. Home Sharing is the next best thing to having my master iTunes library synced up between iMac and laptops. From my laptop, I can load the shared library, play songs and the metadata is updated when finished, which keeps my organizational schemes intact. Plus, I can use Home Sharing to move actual files between the master library and a satellite library, which helps improve my management workflow. The only thing I can’t do is edit the song or any playlists on the remote library. But that’s a limitation I can live with.

This is such a big breakthrough for me, that I don’t think I’ve been this excited since the invention of smart playlists. I’m just ashamed it took me two years to figure it out.

From the comfort of my couch, I can, within the span of seconds, be listening to any song in my collection. And for everything else, there’s Spotify.

App: TonePad- Tenori-On for the rest of us

Allow me to share with you one of my favorite apps in all of Apple’s App Store: TonePad. You see, I’ve been intrigued by the elusive (and expensive) “visual music composition device” known as Tenori-on since I first heard about it a couple years ago. And since I don’t have the time to make the most of a thousand dollar diversionary investment like the Tenori-on, only an intrigue it has remained.

Which is why I took notice when I first read about TonePad, an app for iPhone/iPod Touch that replicates a part of the Tenori-on concept. And since downloading it, I can’t stop making minimalistic, dreamy tunes with it.

Usage is straightforward and simple. On launching the app, the user is presented with a 16 x 16 grid of dots, where the rows represent the beats and the columns represent 16 tones, with higher pitches at the top of the grid. Press a dot to activate that particular note and each time the measure loops to that beat, a tone is played. For visual feedback, each dot pulses as it is played. Combine dots into chords and melodies, and voila, you’re making music.

The tones themselves are pleasant, with a small reverb applied, making it hard to create a “bad” song. Sure, swiping a finger across the interface may not make for the most compelling of compositions, but it certainly doesn’t create the mess that mashing a keyboard or piano does.

As fun as TonePad is though, it does suffer from some limitations. For one, the composition options are fixed. The tempo, time signature and tone are set to a default, and on a default they must stay. You can’t make the loop any faster or slower, or change the number of beats in the measure or change the basic sound of the tone (or make it another sound entirely). Also, you’re limited to working within just the one loop. It would be pretty nice to be able to set up a loop and have it continue to play as you put together another loop to layer on top (and it would be especially nice to do it with different base tones). Finally, and this one can’t really be helped, but the dots are small enough that they can be troublesome to accurately press. There have been a number of times when I wanted to turn one off and ended up turning the neighbors on.

But hey, I’m not really complaining. TonePad is both fun and free and a worthy app to carry in one’s pocket.

Enjoy some TonePad improvisation from yours truly:

On the Web:

Smart Playlist Idea: The Anniversary Playlist

Ever wonder what you were listening to three, four, five or even ten years ago? Or maybe you want to look back and wonder “have I really been listening to this album for that long?”.

Enter The Anniversary Playlist.

By setting two simple Date Added parameters in a Smart Playlist, you can make a self-updating playlist of all the music you were listening to a given number of years ago. It makes a great little time machine.

Here’s one to get you started: 5th Anniversary Tunes.

Anniversary Playlist
click for full size

No matter how far back you want to go, you only need the Date Added selectors and a little simple math.

First selector: Date added is in the last XX months
This criteria includes every song you’ve added to your iTunes library in a given number of months. Since we’re talking years here, we need to multiply the number years by 12 to get the number of months. 5 years = 60 months. But since we want to have a slice that’s slightly older than 5 years, we add 1. So all music that was added in the last 61 months is added to the playlist.

Second selector: Date added is not in the last (XX – 1) months
But we don’t really want our playlist to include all the music that’s been added in the past 61 months, so we use this criteria to exclude everything that’s newer than 5 years old. This leaves us looking at a window of exactly one month from 5 years ago. As each day passes, the window moves and older songs drop away and are replaced with the more recently added.

Looking at my library, I see a number of songs from March 2004. It seems that it’s now been five years since I discovered Elbow (which makes me wonder the aforementioned “has it really been that long?”) as well as filled out my Stereolab singles collection. Also, Tortoise needs a new album. It’s been five years since the last one.

To adjust the window, simply change the number of months back to look. One year ago would be 13 and 12 months, six would be 73 and 72, and so on.

iTunes Tip: Back-date the songs in your library

I’ve mentioned before that one of my standard library organization procedures is to back-date the “Date Added” field for all the songs in my iTunes library. That is, if I originally received an album for my birthday in 1999, I make sure the Date Added field in my library is my birthday, 1999. Same goes for every CD I’ve bought or mp3 I’ve downloaded.

Unfortunately, Apple for whatever reason, has decided that the Date Added field should not be user-modifiable. You can’t change it yourself, either manually or via AppleScript. And honestly, I’m tempted to think of that behavior as a bug/product defect. In this digital age, where at some point each and every iTunes user *will* have to rebuild or replace their library after some sort of data catastrophe, it seems like an obvious feature to be able to reconstruct one’s musical history chronologically. Why should users have to settle for the post-reconstruction dates for albums they’ve actually owned for years?

Well, there’s a bit of a workaround, but it is a tedious one. So make sure you regularly backup your iTunes Library file so that you don’t have to do it all over again in the event of a hard drive crash. I use my .mac/Mobile Me account to upload my library file to my iDisk every night at midnight.

How To

The secret is that iTunes relies on your computer’s system clock to assign the Date Added to songs in the library. So back-dating is as “simple” as changing your computer’s clock, dragging your music files into iTunes, then resetting the clock to the current time.

If you have hundreds of albums to do this with, the procedure can get quickly tiresome. Unfortunately, there is no way to automate it. Plus, if you are trying to fix songs that are already in your library, you have to remove them, change the system date, then re-add them. In those cases, make sure you note the play counts and star ratings, because you’ll have to re-enter those manually. Like I said, tedious.

But all that work is worth it when, in the span of five seconds, you conjure up a Smart Playlist called Best Music from High School:

Date added is in the range 8/15/1993 - 5/15/1997
My Rating is 5 Stars

That is truly awesome.


One warning though:

If you are using Mac OS X 10.5 (Leopard) and you use iCal alarms, be sure to disable them in Preferences before setting your clock back. I found this out the hard way when I was suddenly flooded by couple hundred notifications for events that had already passed. It seems that iCal travels back in time with you, then when you return to the present, it feels the need to update you on all the stuff you missed.

Smart Playlist Ideas: Master List and Newest Tunes

With more than 16,000 songs to manage, there is no more essential a tool in my library than iTunes’ Smart Playlists. From building simple playlists for listening to creating complex queries for examination, Smart Playlists turn what would be a tedious burden into a trivial task. At the moment, I have more than 50 of them slicing, organizing and corralling my expansive collection of tunes into an easily navigable, self-sustaining ecosystem of music.

It seems a shame to keep all those playlists to myself when they could be benefiting other iTunes users, helping them find new ways to organize and listen to their libraries. On this first of a new tunequest segment, I’ll share some of the criteria for playlists that I’ve developed to help manage my library.

This first installment is a two-for. We’ll start with the foundation of my listening habits: the master tunequest list.

The master tunequest list was one of the earliest Smart Playlists I created. Its job is to act as a filter on the main iTunes library and determine which files are eligible for inclusion in other Smart Playlists. The premise is that only properly tagged music without any playback glitches should be included in subsequent lists.

Podcasts, audiobooks, iTunes U courses, videos and other files that are not strictly musical should be excluded from the standard rotation. But how to do it?

master tunequest smart playlist selectors

This is the actual criteria for my master list. There are multiple ways to create one, you just have to tell iTunes what to exclude. Here’s a brief description of the selections I’ve made:

Date Added is not 1/3/02.

I had a major hard drive crash on 1/2/02 which wiped out an early version of my Library. When I restored it from back up the next day, I discovered that the id3 tags for 5 years worth of mp3s had only been made on the library, not the back ups. I took the crash as an opportunity to re-evaluate my songs and make sure that all my files were “up to code” with proper tags and acceptable bitrates.

When Smart Playlists were introduced later that year, I didn’t want songs that I hadn’t checked going into my rotation. With the Date Added for all 7500 songs (my library size at the time) set to 1/3/02, I was easily able to exclude those songs that were pending evaluation. After evaluation, I re-imported my songs with the appropriate Date Added and they were automatically re-included in the master list. Today, about 200 rather obscure songs remain that I haven’t had the wherewithal to track down, so excluded they sit.

Date Added is a powerful tool for segmenting your library based on time period. You can set it to before, after or between dates to isolate just those songs, like a “Songs of Summer 2005” playlist (Date Added is in the range 6/1/05 and 9/1/05).

My Rating is not 1 Star

Rating a song 1 star is my arbitrary way of taking a song out of circulation. If I notice a song has glitches or that its tags have errors, I’ll mark it as 1 star until such time as I can fix it.

Podcast is false

Keeps podcasts out.

Playlist is not SpokenAudio

I have several playlists of just spoken audio that isn’t an iTunes Audiobook: iTunes U courses, comedy albums and other spoken word pieces. These playlists are kept in a sidebar folder called “SpokenAudio,” which iTunes treats as a single unified playlist for the purposes of Smart selecting.

You can create some complex hierarchies and conditional listening schemes using nested folders and playlists.

Kind does not contain video

Keeps all video content off the list. Movies, TV shows and video podcasts are not welcome here.

Playlist is not Audiobooks

Keeps files from iTunes’ Audiobooks sidebar from mixing with music. iTunes offers similar selectors for Movies and TV Shows as another way to exclude video content.

Genre is not Podcast

Another method to exclude podcasts from everyday listening.

Playlist is not xmas

I have a playlist dedicated to Christmas and other holiday tunes. This selector keeps it out of the way for ~330 days of the year. I remove it on or around Thanksgiving and replace at after New Year’s.


Now that we’ve cordoned off our healthy files, we can slice and sub-slice it to fit as many different listening schemes as we have whims. This is a relatively recent playlist I’ve been using to handle new music.

Newest Tunes

Some music falls through the cracks around here. Some albums get overshadowed and as time marches on, they don’t get the attention they deserve, receiving only cursory glances before being supplanted by newer music. This playlist is meant to allow all new acquisitions to have an full opportunity for listening.

It takes 4 parts:

Playlist is master list

The master list ensures that only “safe” music is eligible for inclusion.

Play Count is less than 4

I generally feel that 3 plays per song is enough to consider a new album adequately vetted. You can adjust it to suit your tastes.

Limit to 150 songs selected by Most Recently Added

This limiter means that the 150 most recently added songs that have been played 0-3 times (and are on the master list) will be included in the playlist. When one song on the list reaches 4 plays, it disappears from the list and is replaced by an older song that meets the criteria. When new songs are added to the library, they automatically appear on this playlist, pushing off older songs.

Since I implemented this playlist, I’ve been able to keep a handle on the inflow of new music into my library. Enjoy.

iPod: Sort Your Albums by Year of Release

daft punk sorted by album title
The iPod’s default behavior is to sort alphabetically.
Here’s Daft Punk’s albums:
Discovery (2001), Homework (1997) and Human After All (2005).

Not that long ago, I was asked by a commenter if I had any suggestions for getting the iPod to sort albums chronologically. By default, the iPod’s behavior is to sort albums alphabetically by title. In iTunes, there’s the option to sort “Album By Year” but the iPod features no such function.

At the time, I didn’t have much of an answer for him other than to put the albums in a playlist and just listen to the songs in chronological order. But in an interesting twist, the pixels in that reply were barely dry before Apple released version 1.3 of the firmware for 5G iPods. After some further discussion, this trick was discovered:

The most noticeable change in firmware 1.3 is the application of iTunes’ “smart sorting” (ignoring “a” “an” and “the”), including recognition of iTunes’ custom “Sort Fields” (Sort Album, Sort Composer), for Album and Composer. The Sort fields allow you to enter any text that you want and iTunes/iPod will use that to order the list of items, while displaying the text from the actual field.

Using the Sort Album field, you can easily put albums in whatever order you like. For example, you could put the Halo number of Nine Inch Nails releases in the Sort Album field to have all items, including singles and remix albums, displayed in the order they were released.

For basic chronological sorting, just put the year in the Sort Album field and voila, the iPod will show the album title, but they will be ordered by the year.

UPDATE: The previous version of this post recommended putting the year of the album in the Sort Album field. This, however, effectively changes the name of the album within iTunes’ logic, making it group all albums of the same year together.

The revised method is to simply prepend the year to the album name in the Sort Album field. This way, each album gets a unique identifier that still sorts by year.

Additional caveat: this tip has the potential (there have been mixed reports) to reorder the listings of the “Album” browser, as the Sort Album field may be applied to it. So if you ever use the iPod’s Album View, keep this in mind. See the discussion in the comments for effects and solutions.

For this demonstration, I’ve selected Daft Punk’s three studio albums:

  • Homework (1997)
  • Discovery (2001)
  • Human After All (2005)

As you can see in the image at top, the default behavior is to display the albums in alphabetical order, with Discovery as the first. How do we fix that?

add a year to Sort Album to sort by release date
click to enlarge

  1. In iTunes, get info on the first song of the album.
  2. Click the Sorting tab.
  3. Enter the year of the album then the album name into Sort Album field
  4. Click OK.
  5. Select all the songs on the album
  6. Right-click/Control-click and select Apply Sort Field > Same Album
  7. Repeat for as many albums as you care to customize

When you next update your iPod, the new data will take effect and the albums will be sorted by release date.

daft punk sorted by year
Daft Punk albums sorted chronologically.

This process works for any 5G iPod that has been updated to firmware version 1.3 (and I assume iPods/iPhones released subsequently) So if you haven’t updated yours, hop to it and then get customizing.

UPDATE 2: As mentioned in the comments, if you have an artist who released two or more albums in the same year, there are two options you can use to sort them appropriately:

  1. If you know the more specific album release date, you can prepend that to the album name.
    Example: If one album was released in March and another in October, use 2008-03 and 2008-10 .
  2. If you don’t know the date, you can order them with a number.
    Ex: 2008-1 , 2008-2 and so on.

Diversion: SRSLY, 1000 SONGS

I enjoy reading Captain Future’s Soul of Star Trek blog for its insightful reflections on the franchise and the role Star Trek has played in changing and shaping attitudes, cultures around the world. I couldn’t help but be inspired by a line in a recent post, and I was off to the LOLbuilder:

SRSLY, 1000 songs in your pocket

We’ll return to your regularly scheduled programming shortly.

5G iPod Problems with Audiobooks, revisited

Lately I’ve been on a tear with audiobooks, managing to cram a number of books in between my regular music and podcast listening. The sudden upswing in interest has prompted me to renew my investigation of the problems the 5G (fifth generation) model iPod has with long-playing books. As I noted last summer, the 5G has troubles with homemade m4b files (bookmarkable AAC) longer than a certain play time.

The iPod will suddenly stop playing an audiobook within a few minutes and return to the main menu. This happens when resuming a book, after having listened to something else or resyncing the device, basically anything that stops rather than pauses the book. When selecting the book again, the iPod starts from the beginning, having lost the bookmark and updating the play count/date as though it had properly finished playing.

Since I knew I would be delving into book territory, I decided to figure out the optimum way of working around the iPod’s inexplicable limitation. And really, for all my experimentation, the only concrete result I’ve been able to find is: 4 hours. 4 hours is about the maximum running time of any homemade m4b audiobook file before the iPod starts wigging out about it. It didn’t matter what I used for my encoding settings, my sample rates, or bit rates or channels or workflow or program. No combination of settings allowed the iPod to play longer than 4 hours without a hiccup, always stopping in the middle of the same phrase.

I even tried this little ingenious trick:

audiobook start time option

I manually set the audiobook’s options in iTunes so that the start time was at the 4 hour mark, hoping to persuade my iPod to at least go for another 4 hours. No dice.

I can say however that the sample rate seems to have the most effect on how long you can listen before the iPod won’t let you pick up where you left off. 22 kHz seems to be the trick. Whether your book is stereo or mono seems to matter little, giving about the same performance. Same for bitrate. However, higher sampling rates seems to reduce the amount of time before you lose the bookmark feature.

There probably are a handful more combinations and techniques I could try, but it takes quite a while to join, encode, test and evaluate each option. If anyone finds something with significantly different results, feel free to drop a line this way.

audiobook builder max part length

In the meantime, I’m glad Audiobook Builder can set a Maximum Part length and will split files so that nothing is longer than what I need them to be. It’s a groovy little workaround.

AirTunes returns to casa tunequest

airport express by Jared C. Benedict (

After more than two years offline, the sweet sounds of AirTunes once again bless the tunequest abode. AirTunes, of course, is the technology that allows wireless music streaming from iTunes to Apple’s Airport Express wireless router.

A few years ago, shortly after the Airport Express was introduced, I picked one up for my apartment when I first moved to Atlanta. I was fortunate that my DSL modem hookup and stereo system sat near each other: the proximity made it simple to share my Internet among my computers as well as play my iTunes library from the office on the other end of the building. But when I later bought a house and moved out of that apartment, the stereo and Internet turned out to not be so conveniently located.

The Airport Express was repurposed exclusively for networking, leaving the stereo woefully underused (for some reason, iPods never quite sounded right with it). And so it remained, collecting dust until yesterday.

After putting off the purchase for quite some time, I bought a new wireless router to take over the networking duties (a Netgear Rangemax WPN824v2), and for nearly half price thanks to “Black Friday” deals. Set up of the new device was rather straightforward. Though not as elegant as the Airport solution, the Netgear offers a handful more features that are suited to a dedicated router, such as site blocking and dynamic DNS services.

Needless to say, after making sure the network was up and running, the Express found a new home under the stereo system. A quick reset and some relatively quick reconfiguration (the AX couldn’t “see” the Netgear network, so I had to manually type its name), and I am once again able to seamlessly play my iTunes library in the living room and entertain the whole house if I want to.

Color me bliss.

airtunes multiple speakers

One thing that has changed with AirTunes since I last used it is the ability to stream to multiple locations simultaneously. Until iTunes 6.0.2 (01/2006), streaming was limited to one destination, either the computer or a single Express. Since then however, it is possible to play music from the desktop as well as up to six Airport Expresses on the same network (depending on network conditions) at the same time. I find that very cool as I can be working in the office, pick up my PowerBook and move to the den and not have any interruption in the music.

With OS X Leopard’s Screen Sharing/VNC, I can quickly and easily control iTunes from my PowerBook as though I were sitting at my iMac. Plus, Party Shuffle suddenly got a lot more useful.