Until iTunes 9.0.2, if you had a smart playlist parameter that said the song had to be unrated un-starred, and — while listening to the playlist — you rated a song, the playlist would stop immediately because the just-rated song would disappear from it.

In the new version if you rate a playing song that disappears from a smart playlist, iTunes simply jumps to the next song and begins playing.

via iTunes gets smart playlist rating bug fix – Finer Things in Mac.

A friend of mine once walked into a souvenir shop and saw a t-shirt with a picture of William Shatner as Captain Kirk screaming “KHAAAAAAN!” from the infamous scene in Star Trek II.  It put a huge smile on his face because we always joked that was Shatner’s finest acting performance, and at that moment he immediately realized we were not alone in our assessment.  There were other people who, unbeknownst to us, shared our amused appreciation of it.

Reading that Apple fixed this smart playlist bug made me feel the exact same way.   I never knew if the “disappearing song” issue was a feature or a bug, but it sure drove me crazy.  I’m glad to see that, once again, I wasn’t alone.

Now that Mac hackers have had some time with iTunes 9, they are uncovering some nice undocumented updates.  These three tips hit the Mac Power Tips feed on Friday, and I thought were good enough to share:

• Create Complex Smart Playlists with iTunes 9

This is great for the playlist hacker.  I have wanted this to be added to iTunes forever and just assumed it was not a priority.  What this does is allow you to create nested boolean queries in your smart playlists, i.e. A AND (B OR C).  Previously the only way to do this was by creating a playlist that was based on an OR clause and then include a rule referencing that playlist in a second playlist (confused yet?).  Great add.

• Add Media to iTunes 9 automatically via Finder

This adds a folder in the Finder that auto-imports any music file.  It is like an Applescript / Automator folder action on steroids.

• Organize the iTunes 9 folder in Finder with iTunes 9

I saw this one first on Daring Fireball. This tightens up the file system under iTunes into a much more logical format as well as doing some house cleaning.

I played around with all of these this weekend – all good stuff.

1. When a co-worker told me Steve Jobs led off the event, I was thrilled.  Best news of the day.
2. I can’t wait to try out Home Sharing on iTunes.
3. Hopefully LPs are retroactive to existing album purchases.
4. Everything else went as expected — evolutionary, not revolutionary.

Andy Ihnatko, of MYDL.me, on choosing the bit rate and file format to use when importing a CD collection:

“Before I did The Big Rip, I ripped a dozen different discs from all kinds of genres at a multitude of settings. In the end, I settled on 256K bitrate MP3, fixed bitrate, as my format of choice.

I’m convinced it gives me the fewest compatibility issues (I had a problem with variable-bitrate tracks on certain streaming devices) and the highest quality audio in a reasonable file size.

I chose MP3 because I couldn’t really hear the difference between an MP3 and an AAC file ripped at the same settings, and I didn’t think the savings in storage was profound enough to overcome MP3’s still-superior acceptance.

I chose 256K because I could easily sense the difference between 192K and 256K bitrate, but I had a hard time detecting improvements in any superior bitrates. Given that my usual music player is a 16 gigabyte iPhone and I dock it every day for fresh content, there’s little need for me to overboard in the pursuit of small files.”

What’s my take?  It is pretty similar to Andy’s.  However, I rip CDs into iTunes at 256K AAC, as opposed to 256k MP3.  I use AAC because it theoretically is superior to MP3, has a slightly smaller file size, and given every device I use can support AAC, I didn’t feel as strong as he did regarding potential compatibility issues.

On the bit rate question, I got to 256K for almost the same reasons he explains.  A couple years ago I did “The Big Rip” at 192K AAC.  At the time I figured it was a good compromise between the higher quality of 256K and the smaller file size of 128K.  Since then, storage of course has gotten cheaper but even more importantly for me, I really began to notice the difference in sound quality when I listened to a 128K or 192K file as compared to a CD, so I’ve been ripping at 256K for a couple months now.

So yes… I have a “Big Re-Rip” coming to get me 100% 256K AAC.  Put that on the someday / maybe list.

After writing about Genius Playlists, I thought it would be good to talk about some simple tips for building better Smart Playlists in iTunes.  The first step for creating great Smart Playlists is to start rating your music, so I am going to walk through the system I use to rate my songs.

One of my core beliefs behind how to best manage your iTunes library is that while we all probably have acquired a lot of music in our iTunes libraries over the years, there really is no value in keeping music that we do not want to listen to or have flowing through a playlist.  I know that sounds completely obvious, but this is the opposite of what most people I know do.  For whatever reason, many people take pride in hording all types of music in their iTunes library even if they have no intention of playing it.  The end result is their Smart Playlists end up sounding not so smart, and they skip through the contents until they eventually get to the songs they like.

A second belief is that you really never need to get more granular than rating a song as “good”, “really good”, or “great.”  Anything more than that is just overkill.  This rating system takes both of these factors into account, so here it goes:

• 0 stars – This one is simple but important.  A 0 star song has never been rated.  I make this distinction because sometime people use 0 stars to indicate a horrible song.  I do not.  Again, if a song is that bad it should not be in your library.  For me, 0 stars means the song is unrated.

• 1 star - Delete it.  This really isn’t a rating, but instead is a technique to use the 1 star rating as a flag.  As I listen to music, I will occasionally hear songs I want to prune out of my library because I do not like them, they have poor sound quality, or for any number of other reasons.  Marking these songs with a single star is an easy way to tag them.  Once you start doing this, you can create a smart playlist called “To Delete” which only contains songs that are rated with one star.  Then periodically you just check the playlist and delete the songs that are in it.  Done deal – library is cleaned up.

• 2 stars – This is a song that has a reason to be in your library but you would never want on a playlist.  A common way I use this in my library is for what I would call transition songs that have a place when you listen to an album as a whole, but you would never listen to by themselves.  For the Who fans out there, Tommy has a handful of 2 star songs that advance the story, but you would not want on a random playlist.  Two examples from the album: “There’s a Doctor” and “Miracle Cure.”

• 3 stars – At this point, we are entering the “good songs” territory.  A 3 star song typically is what I would call an album track.  These are songs that are good, but not great, and you might have because they are part of an album / CD, but they are not going to find their way onto a greatest hits collection anytime soon.  To continue with the Tommy analogy: “Cousin Kevin”, “Tommy, Can You Hear Me?”

• 4 stars – Really good songs, but not at the highest echelon.  On Tommy: “Sally Simpson”, “Smash the Mirror”, “Sensation.”

• 5 stars – Simply the best.  Again using Tommy as my example: “Amazing Journey”, “Sparks”, “Overture”, “Pinball Wizard”, etc.

This rating scheme provides support for building great playlists and really keeps it simple — there are no 1/2 stars or additional degrees of judgment here (and yes in case you were wondering, iTunes supports 1/2 star ratings although it is not obvious in the interface).

I would also advise that the best way to rate songs is to do it as you listen to them as opposed to blocking out a full day to work through your entire library.  If you try to do it in one fell swoop, it is simply not going to work – you will get burned out.  You will also avoid developing a massive guilt complex about seeing unrated songs if you have set your own internal mental expectations that it is a gradual process.

Rating songs is the basis for creating great Smart Playlists in iTunes.  In a subsequent post, I will talk about some ideas on how to leverage this rating scheme to build various Smart Playlists that should be in your library.

Over the years, I have done a fair amount of tinkering with smart playlists in iTunes in a never-ending quest to get that “ultimate” mix of great music out of my music library, so I was really excited last month when Apple added “Genius Playlists” to iTunes 8.  While I had played around with the feature somewhat, I did not really give it a good workout until this past weekend.  I took advantage of the eight hours I was going to be in the car driving up and back to a friend’s wedding, and loaded up my iPhone with 100% Genius Playlist-powered music to listen to over the entire trip.

What is a Genius Playlist?

Apple released iTunes 8 in September and Genius Playlists was one of the marquee additions to the update  The concept is pretty neat  Basically, you select one song out of your library, and then iTunes will pick songs from your music library that it deems “similar” to the selected song and automatically build a playlist of songs around it.  Apple says that the algorithm to pick songs

is based not only on your individual profile and library, but also data about music preferences that it gets from the network of iTunes users.  As a result, Apple claims that the accuracy / effectiveness of the Genius Playlist system will improve over time.

To get the Genius Playlists functionality working, you need to activate it in iTunes first by clicking “Turn on Genius” in the new Genius Sidebar.  Once it is activated, iTunes indexes all of your music, and also gets your ok to send anonymous usage data about your music to the iTunes store.  Apple has been very clear that all data sent to iTunes is anonymous, so your individual music preferences are not tied to you.  After this indexing process happens, you are ready to go.

The process of creating a Genius Playlist is simple.  You pick a song, click on the genius icon, decide how many songs to create in the playlist (25, 50, 75 or 100), and optionally click save if you want to permanently keep the playlist.

What Makes A Great Playlist?

If I had put together a wish list of the characteristics of the playlists that I wanted Genius Playlists to create for me, it would have been something like this:

1. Mix in both “hidden gems” and well-known tracks.  For example, if Genius was going to pick a Led Zeppelin song and always picked “Stairway to Heaven” and never anything else, I would have a serious problem with that.
2. Select good music from my library that I have not listened to recently.  I know I have great songs sitting in iTunes that I just have not heard in months if not longer.  I want Genius to pick a handful of those into my playlist.
3. Figure out songs that go great together that I would not have picked if I had manually created the playlist.  I want iTunes to be smarter than I am about why certain music connects to other music in my library.  That is the whole point, right!

When I was loading up my iPhone for the car trip, I decided that I was going to try  it out with a number of different types of music.  My ibrary probably is like yours in that there are several different genres or themes of music in it that would create one horrible playlist if I just hit shuffle on my whole library.  One of my questions going into the test run was if Genius was smart enough to segregate the different genres.

How Did Genius Do?

I created five playlists of 100 songs each, and a couple of the playlists were just spot-on and hit on all of the above factors.  To give you an example, I based one playlist off of The Band’s song “Atlantic City.”  What types of songs did iTunes select?  A smattering of Bruce Springsteen (he originally wrote “Atlantic City”), songs from Bob Dylan (The Band backed Dylan before they made it on their own), as well as artists within the same genre such as the Allman Brothers, the Rolling Stones, and Neil Young among others.  One of the “hidden gems” it selected was “Incident on 57th Street” off of Bruce Springsteen’s The Wild, The Innocent & The E-Street Shuffle album — not a well-known song, but a great one.  This playlist is actually now on a very regular rotation.  Genius Playlists really nailed it.

In another example, I based a playlist on Pearl Jam’s version of “Love, Reign O’er Me”, a song which is originally by The Who.  The Genius Playlist did exactly what I would have expected — it mixed both grunge artists with “Who-era” artists and songs.  The playlist was a good mix of songs from Soundgarden, Led Zeppelin, Stone Temple Pilots, The Who, Smashing Pumpkins, and more.  Another playlist was based on a Mighty Mighty Bosstones song, “Hope I Never Lose My Wallet,” and it did a great job picking ska bands and songs that just felt right alongside the Bosstones.

I did have one playlist that I thought was more wrong than right though.  I based a playlist on “Same Old Song and Dance” by Aerosmith and somehow Genius Playlists made a connection to the “hair band” music in my library, and I ended up with way too many songs from the likes of Poison, Warrant, and the like.  That playlist lasted about 3 songs before the skipped songs outweighed the ones I was actually listening to.

As a whole I would give Genius Playlists probably an eight out of ten.  For the most part, it hit on what I was looking for, but most importantly to me, creating the playlists required basically zero work on my part which was HUGE!  Moving forward it would be nice if Genius Playlists had a feature to give the song selection a thumbs up or thumbs down and then use the feedback to learn your musical tastes  (Pandora has this feature).  Also, at times it duplicated artists a little too much within the playlists, but I do believe Apple will be able to improve the algorithms once they analyze all that data that is getting sent to them.  For me, the killer feature of Genius Playlists is the ease of creating good playlists in a matter of seconds.  I expect to be using Genius Playlists quite often moving forward.  You should definitely give them a try!