Why You Should Be Using Smart Playlists in iTunes and How to Do It, Part 1

I’m a geek. That means i like to organize techy stuff so that it does cool things. This is one of those things i’ve gotten pretty good at, and i want to share what i’ve learned with you.

I have 28 Smart Playlists set up in iTunes. There are also several Smart Playlists that iTunes sets up automatically, but i mostly don’t use those. I also have 23 regular (non-smart) playlists. I’ll explain how and why to use regular vs smart playlists, and what reasons you might have to make use of both for different purposes.

There is a lot of hate towards iTunes. Some of it is even justified. I think Apple made a serious error in combining owned personal music with their streaming platform Apple Music. It gets very complex and confusing trying to make playlists when you are dealing with owned files and streaming music. In addition, the combination of iTunes Match, Apple Music and your personally owned music files has resulted in people accidentally deleting their own personally owned files. iTunes as it currently exists is bloated and confusing. However, in spite of that, iTunes is very powerful and useful, once you can wrap your fingers around its intricacies. That’s what this post is for.

According to Apple. The average iTunes user has between 2,000 and 3,000 songs in iTunes. There are music collectors/aficionados who have well in excess of 100,000 songs. I have right now, 13,768 songs. iTunes can effectively handle each of these sized music libraries when disk space is sufficient.

Examples Of The Kinds Of Things Smart Playlists Can Do

I have several Smart Playlists which i’ll use here as an example of the kinds of things you can do once you start down this path. I will show you how to actually create these Smart Playlists in Part 2 of this post. For now, these are examples of the kinds of things you can do.

Memories – This playlist plays only rock songs released between 1966 and 1980 and that i’ve rated as 4 or 5 stars. Basically, this plays my favorite songs between when i was in junior high and when i got married. That’s the age when we form our most intense musical attachments. These songs will always bring a warmth to my heart when i here them. In order to create a Smart Playlist like this you will need to rate your music, assign genres to all your music and also correct the date of the music. By default, almost every song is dated the day it was released in its most current form, not the date it was originally released. As an example, songs by The Monkees show up as dated 2011 when they were remastered by Rhino and not 1966-1968 when they were actually released. To make a playlist like this work, you will need to google each of your albums to find the original release date. I’ve found wikipedia the best place in general to get this information most of the time. This can be a daunting task when you have thousands of tracks, but is easy to do each time you purchase or rip a song.

CSN&Y – My goal for this Smart Playlist was to have a playlist with songs by every permutation containing one of these 4 musicians and only songs i’ve rated 4 or 5 stars. This is more difficult to construct than you might think, because these 4 guys have produced music in an almost infinite combination. Well, that’s an exaggeration, but not by much. The Smart Playlist must have an entry for each permutation. This includes: Crosby Stills Nash & Young, Crosby Stills & Nash, Crosby & Nash, Neil Young, Buffalo Springfield, David Crosby, Stephen Stills, Graham Nash, Manassas, The Hollies, and The Au Go-Go Singers. In case you are wondering why not just include every artist containing Crosby, Stills, Nash or Young – such an entry would get you songs by Bing Crosby, Lester Young and others. Keeping the Smart Playlist to just these 4 guys took a while and some tweaking.

Summer Music – This wasn’t as hard as CSN&Y, but i took a different approach. I wanted only songs rated 4 or 5 stars, but I wanted songs by The Beach Boys, Bob Marley, The Ventures, and Jimmy Buffett. In addition there is one particular John Denver album (An Evening with John Denver) which has summer memories for me. I also wanted to include the single song Summer Breeze by Seals & Crofts and the single song Summer’s Here by James Taylor.

I’ll show you how to actually create these and other Smart Playlists in Part 2 of this blog post.

Regular Playlists

Screen Shot 2016-09-03 at 2.57.21 PMiTunes allows you to set regular playlists by clicking on File -> New -> Playlist. You then give your new playlist a name. Once you’ve done that, you can put any songs you want into that playlist by dragging and dropping them or by my preferred method, right clicking on a song or group of songs and selecting the ‘add to playlist’ option and choosing any playlist from the list. The regular playlist is most useful for setting up specific playlists which don’t lend themselves to characteristics or data available for automatic selection. For example, i have a playlist set up for Romance which has hand selected songs which cross genre lines and other criteria. On the left is a screen capture of my Regular Playlists. You can place any song, regardless of genre, rating, artist or any other criteria into a regular playlist. The positive aspect of regular playlists is that they are easy to set up and populate. The negative is that they are static. They don’t change no matter how many times a song is played, and they must be manually updated when you get new music you want to add or tire of old music and want to remove some songs.

Smart Playlists

Screen Shot 2016-09-04 at 6.09.11 PMSmart Playlists are where the power is. Smart Playlists can change automatically and dynamically as songs are playing and when songs are added to iTunes. You have the ability to have songs automatically added to a Smart Playlist based on all of these criteria to the left. And best of all, you can combine these criteria in many ways to both include and exclude songs from your playlist.

Organizing Your Music Collection

Ok. I know that most of you are not going to like this. Please keep reading anyway. Organizing your song data sounds like work, but the benefits are so significant that it is very much worth the time it may take.

Most people just throw everything they buy or rip into iTunes and then when they want to listen to some music, they select an artist or an album to play and skip songs that pop up which they don’t like. There is a better way, but it involves doing more than just putting music into iTunes. In order to be able to manipulate your music into and out of smart playlists, you need to add or modify some data about your songs.

Data to add to your music:  genre, rating, release date

Genre – Most music comes with a pre-assigned genre from whatever source you obtain the songs. I have two caveats. Sometimes the song genre is wrong (this happens most prevalently with artists who cross genres such as Van Morrison). More often than wrong genres are genres which are not useful to you. I suggest deciding on 5 to 10 genres that you personally want to use for your music as a way to sort and build playlists, then changing your music’s genres to be in one of those genres you’ve chosen. I tend toward broad rather than narrow genres. For instance, in Jazz there are many sub-genres such as vocal jazz, smooth jazz, swing, big band, bebop, dixieland, and many many more. I set all of my jazz music to either Jazz or Big Band because i’ve used those two genres to set up playlists. Blues can have many sub genres, but i just use Blues. I also use the genres: Classical, R&B, Folk, Rock, Christmas, Country, and Gospel (which i use for all Christian types of music from Gregorian Chant to Gospel Quartets to Contemporary Christian). Your choice of genres may be very different than mine. The key is to narrow the genres down to just ones which you find useful for setting up playlists.

Rating – I’m sure you noticed in my examples above that i often only include songs in a playlist which i’ve rated as 4 stars or 5 stars. In order to be able to do this, you will need to rate all your songs. The easiest time to do this is when you first add a song or album. However, you will notice over time that how you feel about a song may change, so feel free to change your ratings up or down for a particular song at any time. If you are using Smart Playlists, they will automatically adjust whenever you change anything about a song (its genre, rating, date, etc). I rate every single song i have, and yes, this can be tedious the first time. Please do not be reluctant to rate songs you really hate. If you are like me, you have a built in resistance to rating a song as 1 star. Get over it. For ratings to work, they have to be realistic.

For me, a 1 star song is one i will never want to listen to again. I have a Smart Playlist set up for 1 star songs. A few months after rating something 1 star, i go back to that playlist and re-listen to each song, at least enough of it to confirm i still hate it. I then delete any song i still hate. Each song with a 1 star rating will either get deleted or have its rating changed upward. Therefore, my 1 star playlist is a temporary holding spot.

I use 2 stars as a rating for things that i never want to have in a Smart Playlist. For instance, I have a regular playlist made up of songs that i use to help me fall asleep or sleep when i am in pain. Those songs are not ones i want to ever play while doing other things. So, i don’t want to delete them, but i don’t want them in any of my other playlists, so i make them 2 stars.

Songs i rate 3 stars are songs which i don’t mind hearing once in a while, like every 6 months or year or so, but songs that i’m not really excited about.

Songs which i rate 4 stars are those i enjoy listening to and never mind how often they may pop up, but usually that’s every few months.

5 star songs are those that get me very excited, make me feel happy, and songs i wouldn’t mind hearing every few days.

In my music collection, about 50% are rated 3 stars, 30% are rated 4 stars and 20% are rated 5 stars.

Release Date – When i say “release date” i’m only interested in the year. I haven’t found any use for knowing the exact date of a song’s release. By default, almost every song is dated the day it was released in its most current form, not the date it was originally released. You will need to use google and wikipedia to get the correct release dates. If you want to use release dates in your Smart Playlists like i do above in my Memories playlist, then you will need to correct their dates. The albums which always need this done are Greatest Hits albums. You may need to google each individual song to find its release date. Often the original release date will be in the album booklet of the CD. If not, then you’ll need to google each song.

Part 2 of this post will contain actual “How To” construct these playlists.

I’ll add a link here when it’s ready.

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The 2 Best Jazz Albums of the 20th Century

There seems to be a solid case for there being two best Jazz albums from the 20th century. However, the two albums are praised by two different groups of fans for two completely different reasons. Jazz enthusiasts mostly consider Miles Davis “Kind of Blue” to be the best Jazz album because of the music. Audiophiles mostly consider “Jazz at the Pawnshop” to be the best Jazz album because of the audio quality, mastering, and the ‘you are there’ presence of the recording.  I have both so i thought i’d compare and contrast them and give you some details about both albums.

Kind of Blue

Kind of Blue

I think the reason this album is so well regarded is that it seems very relaxed and listenable while at the same time being extremely complex and nuanced. Those who are not jazz enthusiasts can listen and enjoy the music on this album because it just seems easy to get and enjoyable, while a real jazz enthusiast can find layers of complex things going on because of the modal base of the music and the extreme talent of each of the musicians to play expertly both individually, yet also as a group. It’s difficult to explain in words, but above all other jazz albums, this one stands up to repeated listening and enjoyment by both true jazzophiles and also average listeners.

The recording process for this album highlights the talent of these musicians as shown in this quote form the Wikipedia article on Kind of Blue:

As was Davis’s penchant, he called for almost no rehearsal and the musicians had little idea what they were to record. As described in the original liner notes by pianist Bill Evans, Davis had only given the band sketches of scales and melody lines on which to improvise. Once the musicians were assembled, Davis gave brief instructions for each piece and then set to taping the sextet in studio.

Kind of Blue has been released, re-released, mastered and re-mastered more than any other album i am aware of. You would think that the reason is because of its popularity, but there is another more complex reason. The album was originally recorded in 1959. It was released on vinyl many times but it was discovered that the original master tape of side one of the album was recorded slightly ‘off’ speed resulting in the pitch of the first side being wrong. This problem was not corrected until a re-master done 33 years later in 1992. All subsequent re-issues and re-masters have also corrected the pitch problem on the side one songs. In addition, an alternate take of “Flamenco Sketches” from the original sessions has been added to re-masters done after 1997. There have been many additional re-masters done since that time using improved technology to attempt getting every single bit of nuance and clarity from those original tapes. The process has been successful to a degree. The newer post 1997 remasters are better than the original releases, but as with most of these kinds of things, it takes some sophisticated (read expensive) audio equipment to catch the minute improvements in clarity of the music and reduction in noise. For most of us, any re-master done after 1997 will give you an excellent listening experience.

In fact, i did a specific blog post comparing the best of the re-masters with a regular CD re-master. If you are interested you can read that post from This link:

Comparing normal and hi-res versions of Kind of Blue and Jazz at the Pawnshop 

Jazz at the Pawnshop

Jazz at the Pawnshop

This album, recorded in 1976,  has long been considered by audiophiles to be one of the best sounding, best mastered jazz albums ever made. It truly makes you feel like you are right there in the club listening to this performance.

The jazz music on this album is good. It just isn’t in the same league with Kind of Blue which is why there is considerable consensus that Kind of Blue is the best jazz album of the 20th century because of its music while Jazz at the Pawnshop is the best sounding jazz album of the 20th century. Both have many who fervently espouse their convictions and i think both can be and are true.

My recommendation to you: get both these albums. Both are listenable and enjoyable even if you are not a jazz aficionado. Both sound good, really good. So if you want to listen to the best jazz music ever recorded in the 20th century, buy Kind of Blue. If you want to listen to one of the best sounding, best mastered, clearest, ‘you are there’ live jazz albums ever recorded, get Jazz at the Pawnshop.

Or, do like i have, and get them both.

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Christmas Music by John

By request, here are two Christmas songs i recorded in 1978. The first one is just me singing White Christmas over an instrumental record by The Rainbow Strings from sometime in the 1960’s. The second song, What is This? is me playing guitar and singing a duet with my brother David.


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All About HDTracks Hi-Res Audio Files

Questions to answer:

  1. Can you hear the difference in hi-res files?
  2. Are the hi-res files worth the extra cost?
  3. Can/How do i play hi-res files in iTunes or on my iPod/iPhone/iPad?

First, here’s why i’m doing this:

I purchased two of my favorite albums from HDTracks.com over the past few months just to play with and see if i can hear the difference between these files and those i ripped from CD’s as Apple Lossless (ALAC) files.

The two albums i purchased are:

Kind of Blue

“Kind of Blue” by Miles Davis (one of the best jazz albums of all time)

Jazz at the Pawnshop

“Jazz at the Pawnshop” (an album widely praised by audiophiles for its sonic awesomeness)











Both of these are albums i’ve owned in several versions over the last 35 years from vinyl through CD and then remastered CD and now in hi-res audio files. I know and like the music very well.

So . . .

1. Can you hear the difference in the hi-res files?

I’m listening with my desktop computer/iTunes and also on my iPod Classic (7th gen) as sources through a Fiio E09i headphone amplifier and AKG K550 headphones with Alpha Pads. Yes, it’s not end game high end audio equipment, but it is decent audio equipment.

In order to be sure that I am comparing apples with apples, I took the hi-res files from hdtracks.com and converted them to standard Apple Lossless (ALAC) files using the process listed below in the answer to question 3.

The answer for me, with my equipment and hearing is an absolute NO. I suppose it is possible that someone with better “ears” and better equipment might be able to hear a difference. However, thorough research in multiple audio forums and articles seems to say that at best, more than 99% of listeners can not tell any improvement in sound quality of the same exact mastering of a musical file based solely on the resolution of the file.

2. Are the hi-res files worth the extra cost?

Unless you are one of those in the less than 1% who can hear a difference, the answer is often (but not always) NO.  As an example of the cost difference, the remastered CD for Kind of Blue costs $7.29 on Amazon.com and $24.98 on hdtracks.com. That means that a hi-res audio file costs more than 3 times what the CD costs for an audio difference that almost no one can hear. HOWEVER, please note that most people can hear the difference between an MP3 file of 256 kbps or less and an ALAC or hi-res file from the same master on good audio equipment.

However, there are several reasons you might, perhaps, want to buy the hi-res file anyway. It might be possible that at some future time audio equipment will be able to play the hi-res files in a way that could make the audio difference hearable. It’s also possible that you have exceptional hearing and are one of those who truly can hear the difference. However, the most likely reason to go with a hi-res music file from hdtracks or from Pono would be because the music files have actually been remastered using superior mastering techniques to those of the commonly available CD version of an album. This actually does happen. Better mastering is often a good reason to buy a high resolution file instead of the CD. BUT, buyer beware. that the mastering actually has to be better than that found on the normal CD and there is no guarantee that just because it is a hi-res file, it has been remastered in a better way. In fact, this is usually not the case. Improved mastering by a good engineer can make a very audible difference, and in those cases, the high resolution file actually does sound better even to my ears on my equipment.

An example in point is the high resolution version of Jazz at the Pawnshop. This album has been remastered many times and the differences are audible, but NOT because of the high resolution files, but because of the mastering techniques used. If you take the newest, best mastered version, and down sample it to standard 16/44.1 CD resolution, there is no audible difference between the hi-res file and the standard file, to me, and to almost all listeners. However, the sound of the newest remastered file in both hi-res and standard is better than the earlier versions, and those were good, in fact, better than good.

3. Can/How do i play hi-res files in iTunes or on my iPod/iPhone/iPad?

Have you ever wondered how to convert hi-res 24/96, 24/192 or other hi-res files to versions playable on an iPod or iPhone? Me too. So i spent a few days doing a lot of googling and reading and then trying the stuff i read. I’ll give you the end result so you won’t have to do all the research.

I am using dBpoweramp R15.3 for all my bit rate and bit depth conversions. There are other programs which can do this, but i’ve been a dBpoweramp user for many years and their software works great and their support forum https://forum.dbpoweramp.com/forum.php is excellent with answers often supplied directly by the software author. The software isn’t free, but it is worth the cost.

I am working under some assumptions:

  1. You want to use the high resolution file in iTunes and possibly on an iPhone/iPod/iPad.
  2. You want the best sounding version of the file possible.

If that applies to you, here is the process to accomplish this. Follow these steps, and do them in this order. Doing these steps out of order can lessen the quality of the audio and/or cause artifacts to be inserted into the music.

Get the file as an ALAC file or convert a FLAC file to an ALAC file.

High resolution files are almost always available as ALAC or FLAC.  There is no reason to get any other file format. Trust me on this. If you want to play your files in iTunes, get an ALAC file. iTunes will not play FLAC files. If you already have a FLAC file, it can easily be converted to an ALAC file using the convert option of dBpoweramp. Make sure you have the codecs installed (they are free) for both FLAC and Apple Lossless. Then right-click on the file and select convert. Choose Apple Lossless as the file type to convert to. Presto-Chango, you end up with an ALAC file!

Convert the sample rate to one which can be used in iTunes or on an Apple device.

The highest sample rate which an Apple device can use is 48 Khz. If playing the file on an Apple device is your goal, then you want to down sample the file to 48 Khz or less. If you want to play the files only in iTunes (either on your PC. Mac or via an external DAC) you need to convert to 96 Khz or less.

You can purchase FLAC and ALAC files at 44.1, 48, 88.2, 96, 176.4, 192 and 384 Khz. Here is the important key: you want to down sample your file to an even multiple of either 44.1 Khz or 48 Khz. This is important. Let me give you some examples:

If your file is 384 or 192 you can convert it down to 96 or to 48. Those sample rates are exact multiples of 48 so when you down sample them, no interpolation is done, it’s an exact division and you will get a new file free of artifacts and errors. If your file is 176.4 it can be down sampled to 88.2 Khz or 44.1 Khz without error or artifacts.

Itunes can play 96, 88.2, 48 and 44.1 Khz files. Any Apple device (iPod, iPhone, iPad) can play both 48 Khz and 44.1 Khz files.

For maximum compatibility, convert your files down to either 48 Khz or 44.1 Khz, which ever is an even multiple of your original file. This keeps the process clean and error free and will give you a file playable on any Apple device. Remember that 99% of us can not hear any audible improvement for a file higher than a 48 Khz sample rate, so my advice is to down sample to 44.1 or 48 Khz (which ever is an even multiple) and not worry about the higher resolution numbers. You won’t hear the extra information, and the higher resolution files take up MUCH more disk space.

To do this in dBpoweramp, go to the add DSP box and select Resample and then click on the settings button and select either 48000 or 44100. You will have to change this setting whenever you start with differing sample rate original files.

If you are going to “volume normalize” using EBU R128 or ReplayGain, do that now.

I am a fan of EBU R128 volume normalization. What is that? Have you ever been frustrated by playing songs in a playlist in iTunes or on your Apple device when one song is quiet and you have to reach and turn up the volume and then the next song blasts your ear drums? Volume normalization fixes that problem.

Apple has a way of doing this called Sound Check. If you enable this feature in iTunes and on your Apple device, then every song you add to iTunes will be adjusted to a common volume level and when played back on an Apple device, you shouldn’t have to keep reaching for the volume control.  Sound check has a few flaws: 1) better methods of analyzing files have been developed which do a significantly better job of matching (normalizing) volumes and 2) this ONLY works when you play back a file on an Apple device. Sound check has two advantages: 1) it does not alter the original volume of the file, it just adds a tag to the file which tells the Apple device how much to raise or lower the volume and 2) you can turn off sound check if you ever want to.

ReplayGain uses a better algorithm for adjusting the sound level. It also works on non-Apple devices, but not on all devices. In order to use ReplayGain, you need to use a program outside of iTunes. dBpoweramp can use the ReplayGain algorithm in its Volume Normalize DSP (digital sound processor).

The best method of Volume Normalization is relatively new and is known as EBU R128 or simply R128 for short. Its algorithm is an improvement on ReplayGain and it works extremely well. I use R128 on all of my music files and i use the dBpoweramp volume normalize DSP to do this whenever i rip a CD or convert a music file. Simply add the Volume Normalize DSP to your conversion setting in dBpoweramp after the resample DSP and then click on the settings button and select EBU R128.

Lastly, convert your bit depth from 24 down to 16.

This should be the very last step in any file conversion. iTunes will play 24 bit files. Apple devices claim they will play 24 bit files, but in reality they do not. They simply lop off the extra 8 bits to get from 24 bits to 16 bits, adding distortion to the music playback. You do not want that to happen, so you should convert 24 bit depth files to 16 bit depth files using a process known as dithering (and selecting triangle for the dither method). I won’t go into the whys and wherefores concerning dithering and why you should use it, but you should.

Let me briefly explain bit depth. When listening to a music file, every file has something called Dynamic Range. Dynamic Range is the difference (measured in db’s) between the loudest sound in a file and the quietest sound in a file. The maximum dynamic range that most humans can hear is 100 db. 16 bit depth files contain 96 db of dynamic range. This is very close to the maximum a human can hear. 24 bit depth files contain 144 db of dynamic range, far more than a human can hear. 24 bits are used when mixing and mastering digital files by engineers in order to allow for extra headroom to avoid clipping. That is a valid reason for using 24 bit files, but a reason which disappears when the file is finally mastered in its last step. Recording engineers use dithering to turn their 24 bit master into a 16 bit master ready for making a CD. You should also use dithering to convert from 24 bits to 16 bits.

Since we are dealing with final files, and since no Apple device will correctly play a 24 bit file without actually cutting out 48 db (144 db – 96 db) of dynamic range in a very harsh manner, we should make converting our music file to 16 bit the last step we take.

Using dBpoweramp, add the DSP Bit Depth to your conversion step. Click on the settings button and select triangle as the dithering method. Using dBpoweramp, you can do each of these steps one at a time. or you can do them all at once. However, dBpoweramp will execute the DSP steps in the order they are entered. You absolutely should drag and drop them so that the Resample step occurs first, volume normalization second, and bit depth is the last DSP.

If you have any questions about any of this information, please leave them in a comment to this blog post.


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B.B. King: A True Legend Has Passed From Us

BB King

B.B. King died last night at the age of 89.  I’ve been listening to his music for around the last 30 years.  My sons have grown up listening to his music.  He had a way of playing a lyric line of blues on his guitar Lucille which was moving and that reached inside you.  He could make you feel his music in a unique and powerful way. He wasn’t concerned with dazzling guitar pyrotechnics. He just let the music flow out.  He also could sing. Better than most, and in a way that complimented his sparse guitar playing.  His voice and his guitar interacted and perfectly complimented each other.

I’m including two of my favorite B.B. King songs for you to enjoy.

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