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.

Smart Playlist Idea: My Favorite Nostalgia

I’ve been having so much fun with a new iTunes Smart Playlist for the past month that I’ve just got to share it. The basic premise is to relive my entire musical history in rough chronological segments, with the goal of drifting through the highlights of the various eras of my musical life. Contemporaneous songs are grouped and played near each other, creating a nostalgic soundtrack to your life.

It’s proving to be a fun trip down memory lane as I associate particular songs with particular moments, like that 10th Grade state science fair trip (powered by grunge supergroup Mad Season), Christmas vacations, the first mp3 I ever downloaded, that first year of college (where my early pop-rock leanings begin to mix with my discovery of electronic music), that first Stereolab track and other sundry milestones.

As I’ve been working my way through the playlist for about a month, each day ha brought great tunes and great memories.

Before we get going, some initial statements about the playlist though:

  • For best effect, you should have a fairly significant musical history. Mine stretches back seventeen years and just going through “the best” songs it’s taken me about a month to listen through the first six of them. The slowness is part of the journey for me though.
  • Chances are, if you have a long music history, you also have a rather large library. Part of the fun that I’m having with this project is the anticipation as I wonder what song will be played next. So, while a large library isn’t necessary for this project, it will be more fun if you have a large pool to draw from.
  • I keep bringing it up, but yes, this works best when the songs in your iTunes Library have the proper Date Added: the date you actually acquired the music, not just the date you added it to your iTunes Library. It’s the backbone of the playlist, really. If you’ve been building your iTunes Library since it came out in 2001, you should be good. If you’ve been collecting music longer than iTunes has been around, see how to back-date your songs. It’s tedious, but worth it.
  • A considerable portion of the songs in your library should be rated. The goal of this playlist is not to listen to every song in your library, but only your favorites from past to present. The star rating is how we filter all the best tunes.

That all said, how do we create this wondrous playlist? It’s actually a very simple couple of selectors.

Making the Smart Playlist

Start a new Smart Playlist and add the following criteria:

nostalgia smart playlist selectors
click to enlarge

My Rating: 5 stars
This makes sure only your favorite songs enter the playlist.

Last Played is Before {today’s date}
This selector initializes the playlist. Any song played before this date is eligible for inclusion. And songs are automatically removed from the playlist after you listen to them.

(Optional) Playlist is masterPlaylist
I use a master playlist to make sure my tunes are on the up and up. It filters my library so that only songs that are properly tagged, with correct date added, etc are included in other playlists. If you don’t have or want a master playlist, you can leave this selector out.

Limit to XX items selected by Least Recently Added
This is what really makes the Smart Playlist work. The number you use for XX really depends on the size of your library and how large a “slice of history” you want to listen to at any given moment. I keep mine between 50 (when I’m listening in iTunes) and 100 (when I’m out with my iPod for the day). The Least Recently Added selector adds the earliest songs (according to Date Added) to the playlist and automatically replaces played songs with the next earliest ones.

Using the Playlist

The most effective way to use this playlist is via iTunes’ Party Shuffle Up Next feature (Party Shuffle is no longer part of the latest versions of iTunes). What I like about this method is that as songs are removed and replaced from your nostalgia playlist, the new songs become immediately available to Upnext, allowing for some really smooth musical transitions. The downside is that you’re chained to iTunes for all your listening.

But you can take that playlist on the road via iPod (or iPhone). It works just like any other playlist. Keep in mind though, that for the true “river of time” experience, try not to listen to the entire playlist in a single sitting when mobile. This has the effect of creating a hard break in the listening by completely clearing out all the oldest unplayed tunes, then replacing them with the next batch of songs. It divides the experience into chunks rather than the “smooth river” that I find so appealing. My solution is to listen to, at most, half the playlist during any given session. That way, when go to update the playlist, the new songs are intermingled with the unplayed ones.


Well there it is, the most fun I’ve had with a playlist in quite a long time. Hopefully, your nostalgic adventure will be as rewarding as mine has been.

Smart Playlist Idea: Eldest Tunes (that need attention)

This is a fun little playlist.

In my last Smart Playlist example, I showed how to create a list of the most recently added songs that had not reached a certain play count. Today’s list takes the opposite tack: what are the oldest songs in the library that haven’t been played a certain number of times. I call it “Eldest Tunes” and it is a great way to give attention to songs in your library that have, for whatever reason, found themselves neglected. I’ve found it to be particularly good for reminding yourself just how much you loved those songs of yesteryear.

Before I continue though, I have to point out that if you started your music collection before July 2002, then this playlist works best if you’ve back-dated your library’s Date Added field.

Setting the playlist up is actually ridiculously easy. Here’s a screen shot of mine:

Playlist is tunequest

Songs must be in my master playlist. If you haven’t set up a master playlist, then you can leave this criterion out.

Play count is less than 4

This number is arbitrary and can be whatever you want. In my case, I want to find songs that have been played 0-3 times. When a song reaches 4 play counts, it can no longer appear on this list.

Last Played is not in the last 3 months

This is a recycling mechanism. If, like in my example above, you’ve set your threshold to 4 and then listen to a song that only has 1 play count, the count increases to 2 and the songs stays on the playlist.

When I first put this playlist together, I found that I was listening to the same songs over and over again for that reason. It was taking multiple listens to rise above the 4 threshold that I had set. So I added this rule that says once a song has been played it is “embargoed” for 3 months, giving other songs an opportunity to be heard.

Finally, the last two criteria:

This is the actual engine of the playlist. Limit your playlist to the number of songs you want, but make sure you select least recently added. That least recent part is why it’s important to have accurate info in your Date Added fields. iTunes uses the date in that field to determine which songs will go on this playlist and in what order.

In my case, the oldest songs that currently appear on my Eldest Tunes playlist are from Primus’ Pork Soda and Blind Melon’s debut. I originally bought them over the summer 1993 (backdated in iTunes), but I’ve hardly listened to them in the past few years, so their play counts are low. But now that I’ve seen that they’ve been under-appreciated for so long, I can take steps to give them them proper consideration.

As for your playlists, I wish you happy listening!

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.

New Hard Drive in the House

coolgear firewire sata enclosure housing a 500gb maxtor maxline pro
My new file storing powerhouse.

I like to keep my eye on on the price of hard disk storage. More storage more better is my philosophy. Not only can I never tell when I’ll need an extra gigabyte or two for projects, but I’m justifiably paranoid about data failure and have become something of fiend for backups as a result. So I’ve been watching with interest as the price of 500GB drives have fallen at a steady clip since the beginning of the year.

My interest was piqued recently when I noticed that a number of external 500GB drives have been hitting the ~$100 area lately, which is nearly too good a deal to pass up. My enthusiasm was tempered though, by the observation that all the drives I found were USB 2.0 only. USB is no slouch and a fine enough protocol, but real file transfers, particularly large ones, are best left to FireWire. Unfortunately, FireWire versions seem to cost $50-$90 more than their USB-only counterparts.

So I did what I’ve done for the last 5 drives I’ve purchased: I looked into do-it-yourself solutions. Assembling an external drive from an internal one plus an enclosure is a trivial task and it helps you get exactly what you want. In the past, that approach has helped me save some cash at the same time.

Unfortunately, the gap in price between internal and external drives doesn’t seem to be as great as it once was. Mail-in rebates can often bring the price of external drives to below that of internals. Realizing that I probably would be out of luck trying to save some dough, I set out to see how much I could get within the price range for an external 500GB hard drive with a FireWire connection ($160-190).

In the end, I think I did pretty well.

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Pioneer DVR-107D DVD burner + Max = Perfect encoding solution

Recently, I’ve taken to re-encoding some of my favorite CDs, mostly ones that I originally encoded long ago, some as far back as 1999. Hard drive space was at a premium at the time, so I traded acceptable losses in quality for a smaller storage footprint. When the music is coming from a beige G3’s internal speaker, 112 kbps and 320 kbps mp3s sound basically the same.

But as I’ve gotten older and I’ve been able to afford audio equipment with higher fidelity, the flaws in those original files have become ever more noticeable.

Since hard drive space isn’t much of a problem these days, I’m endeavoring to upgrade all those ancient files to modern quality standards. As I run across those sub-par album rips during my daily listening routine, I’m replacing them with 256 kbps VBR AAC files or Apple Lossless (if they are deserving of the extra attention to detail).

Max Icon

And so was this situation that occurred last week when listening to Velocity Girl’s ¡Simpatico!, one of my all-time favorite albums. The music sounded “off” and it reminded me that I’ve been meaning to create a new encoding for a long time. I grabbed the disc off the shelf, fired up Max, the handiest freeware audio converter/ripper/encoder available for Mac OS X, and set it to work.

But it did not take long for an anticipated problem to rear its head. The seventh song on the disc, Rubble, has had a pretty nasty scratch for I don’t know how long, a scratch that marred the original file years ago. As I feared, the encoding process stalled, so I canceled it. I’ve known my iMac’s built-in Matshita UJ-846 drive to be problematic with flaky discs, frequently getting hung up on them, so I pulled out my external Pioneer DVR-107D and hooked it up via Firewire.

The DVR107D was one of the first DVD burners available for less than $100 and I got one to use with my G4 iMac, which couldn’t even read DVDs, much less write them. I crammed the drive into an old LaCie case I had and, let me tell you, this thing has performed like a champ for the entirety of my ownership. It has read every disc I’ve put into it. And recently, it allowed me to consolidate some old, and I mean old, CD-Rs onto DVD when the built-in drive balked at them.

So I slipped my CD into the Pioneer and resumed my encoding task. No hang-ups whatsoever. But the thing that blew me away, and I have Max to thank for this, was that when I listened to the new song, all traces of the disc damage were gone.

It turns out that Max leverages the power of an obscure CD audio extraction tool called cdparanoia which uses “high-level error-correction” to resuscitate heavily flawed discs, and completely compensate for scratches on CDs.

Combined with Pioneer’s hardware, Max turns out perfectly encoded songs. Just give it a listen. The following are from multiple encodings excerpted from the damaged section of Rubble from my Velocity Girl CD:

This first sample was encoded to 128kbps AAC/M4A by iTunes 4.7 using the built-in CD drive on the iMac G4 I owned two years ago. The glitches on the disc is quite prominent:

Audio clip: Adobe Flash Player (version 9 or above) is required to play this audio clip. Download the latest version here. You also need to have JavaScript enabled in your browser.

This file, however, is golden. It was encoded to Apple Lossless by Max using the Pioneer DVR-107D. Pristine; nary a hint of trouble:

Audio clip: Adobe Flash Player (version 9 or above) is required to play this audio clip. Download the latest version here. You also need to have JavaScript enabled in your browser.

Frankly, I’m amazed by the results. Max + Pioneer makes for a seriously perfect encoding solution.

The DVR-107D shipped as the standard optical drive in some (but not all) of the PowerMac G5 towers, so you may already have one. If not, at the time of this writing, Other World Computing has its descendant, the DVR-112D for less than $50.

Even if you don’t have access to the drive itself, download Max. It’ll go a long way toward creating higher-quality files.


PS: Google Docs, which I use to store drafts for this site and other correspondences, now works with the new Safari 3 beta from Apple. This post was written using the combo and it’s nice to have my familiar Mac OS Services, integration and text and keyboard handling at my disposal.

The $200 terabyte has arrived

western digital my book

A couple months ago, I wrote about the advantages of maintaining a large digital music library, specifically with regards to cost and storage as compared to maintaining a large physical music library. One of my points was that the decreasing prices of hard drives makes it increasingly easy to store, as well as backup large quantities of high-quality music.

I even went so far as to say that “before too long” we’d see the $200 terabyte, which is roughly enough storage for 80 continuous days of lossless quality music plus a complete backup of it all.

Well, that day has arrived. OfficeDepot currently is listing a Western Digital My Book 500GB for $99 after mail-in rebate.

At that price, you might as well get two and secure all your digital media.

Tagging Remix and DJ Albums for iTunes and iPod

Remix albums and DJ albums have always proved a challenge to tag in a useful and logical manner because of how they differ from the traditional song-artist-album tagging model. Like compilations, remix albums typically include songs by a variety of artists and musicians. But they are released under the banner of a single artist and it is that artist that I associate that album with. For example, the album Brazilification has tracks by 18 different artists, all remixed by Fila Brazilia. Most, if not all the songs had been published before on each of the remixed artist’s own records or singles, but Brazilification collects them all and releases them under Fila Brazilia.

Oh what to do, what to do? The standard tagging fields don’t offer a clean way to deal with remix albums, so I’ve had to cobble together my own solutions. The methods I use have to be simple and straightforward to use on an iPod, whose navigation options is more limited than iTunes, but it also has to include all the pertinent information, song name including remix title, remixer, original artist and the album (plus genre and year).

Below are the two approaches I’ve developed. Neither one has really worked to my 100% satisfaction, though.

Method One: Remixer as Artist

This scheme is the more predominate one in my library. I’ve been using it for a long time, but have never been that happy with it. In a sense, the remixer is treated as though they have created a cover version of the original.

Artist Tag

Iin my mind, I associate the remixer/dj as the primary artist. It does have their name on the album cover after all. Thus, using the example above, Fila Brazillia is listed in the Artist field.

Album tag

The album tag, of course, is the album name.

Song Title

There’s no easy way to account for, identify and display the originating artist when the remixer is using the Artist field, so they are added to the beginning of the song name using this syntax:

Radiohead: Climbing Up the Walls

This way, I can easily navigate to the album on my iPod, glance at the track listings and see both the original artist and the song title.

Composer Tag

To make locating remixes in general easier, using my Composer tag guidelines, I identify the original artist again in the Composer tag, but surrounded by parentheses to separate them from actual composers.


This approach doesn’t work semantically. It puts inappropriate data in inappropriate fields in order to make the system function. To continue with the example above, song is technically titled Climbing Up The Walls (Fila Brazillia Mix) and the actual artist is Radiohead. If I had a copy of Radiohead’s Karma Police single, where the remix originally appeared, Radiohead would, quite properly, receive the artist tag.

Also, The scheme doesn’t play nice when my iTunes library interfaces with third-party applications. The song above is submitted to as Fila Brazillia – Radiohead: Climbing Up the Wall, which acheives a disservice for both artists. On the site, it pollutes Fila Brazillia’s database of songs and at the same time, doesn’t provide proper credit to Radiohead.

Because the Artist tag has been misappropriated, this contorted design can interfere with statistics. And anyone who’s spent time around here knows that when it comes to my iTunes library I’m a statistics nut.

Brazilification using this first method. click to enlarge.

Additionally, I find it redundant to enter the original artist in two different places. I’ve been relatively unhappy with the scheme, so I recently began to explore other options.

Method Two: Remixer as “Composer”

One idea I’ve been toying with is swapping the Artist and Composer tags in the above scheme. Thus:

Artist Tag

The original artist name. (Ex. Radiohead). Gives appropriate credit source artists and allows them to be included in Smart Playlists that factor artists.

Compilation tag

Under this configuration, there would be multiple artists on the album, so the Compliation check box must be checked.

Album Tag

Takes the form of Remixer/DJ: Album Name (ex: Fila Brazillia: Brazilification). For easy identification when browsing. However, it does present another semantic problem in that it offers more information the album’s actual name. So the remixer could be left out. I’ll have to see how it works in practice.

Song Name

Song name (remix) (ex: Climbing Up the Walls (Fila Brazillia Mix). It’s only appropriate to give each song its appropriate name.


The remixer, again surrounded by paranthasese to keep it separated and sorted from actual composers.

Instinctively, I like this design. I’ve not really had a chance to implement it on a large scale, but it holds potential to address the concerns I have with my current scheme.

Yes, it still has some redundancy, with the remixer listed both in the song name, album title and composer tag. However, with direct compilation support on newer model iPods, the use of the remixer in the album or composer tag could be omitted.

Using the Album Artist tag to identify the remixer/dj would actually solve all the problems with this plan. But the iPod’s current lack of support for the field leaves me having to use these workarounds. Let’s hope that Apple adds that increased functionality soon.

In any case, this new tagging format promises to make it rather easy to locate and identify all the songs, artists and remixers in both iTunes and the iPod. It also will work with submissions and sorts everything nicely for my all-important statistics.

Brazilification using this second method. click to enlarge