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Use a Smart Playlist to Fill Your MP3 Player

While yesterday's review of Microsoft's new Zune was being edited, a question came up: What's a good way to describe a "smart playlist" to the uninitiated?

As we tossed around a few phrases to add to the story, I showed how I used one smart playlist to automatically load a new selection of songs on an iPod. My editor (and podcast co-host) Greg Schneider thought this playlist recipe was worth sharing, so I said I'd document it here.

The first step is to figure out how much music you want to load each time. In my case, that's not as much as the iPod's capacity -- I like to carry around a few of photos and maybe a subway map or two. On a 4-gigabyte iPod nano, that means I'm going to want about 3.6 GB of music each time.

Then you want to tell iTunes to vary the selection, but without giving you things you might have just heard or skipped past. The last ingredient: Make sure you're not presented with any Christmas music in in the middle of June.

The screen capture here shows what I came up with:

* "Last Played... is not in the last... 60 days" should keep me from hearing anything too familiar;

* "Last Skipped... is not in the last... 60 days" does the same for music I disliked enough to jump past instantly;

* "Genre... is not... Holiday" clears out the Christmas music (provided it's all been filed under that genre);

* "Limit to... 3650 MB... selected by... random" is the most important part (my initial version of this recipe consisted only of this item);

* "Live updating," when enabled, tells iTunes to reshuffle this selection.

(You can do about the same thing in Windows Media Player, except that program doesn't track when you last skipped a song. Go to the Library menu, select "New Auto Playlist"; click the plus signs below "Music in my library" to limit the playlist to songs with a "Date last played" before the last 30 day and a genre that is not holiday, then click the plus sign below "And apply the following restrictions to the auto playlist" to limit its total size.)

Name this playlist something obvious -- in my case, "Random." Finally, tell iTunes to load the iPod with that playlist only. Select your iPod in the left-hand column, click the Music heading in the center pane, click the button next to "Selected playlists:" and then click the checkbox next to your new smart playlist.

Does this recipe work for you? Any changes you'd make? Let me know in the comments...

By Rob Pegoraro  |  November 16, 2007; 1:00 PM ET
Categories:  Tips  
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The Windows Media Player auto playlists are annoying in the respect that they don't handle multiple criteria very well.

So if I say that I want all tracks which are performed by X, OR are written by X, then any tracks where X performed and wrote will be added twice. If you have additional criteria that are met, then the track will be duplicated for each criterion.

Posted by: Mike | November 16, 2007 2:01 PM | Report abuse

Nah. I've never been satisfied with any smart playlist program. My thinking on music selection is essentially the logic mind-bender Kirk would use to confuse the logic robots.

Posted by: dgc | November 16, 2007 4:08 PM | Report abuse

I've done this in the past, but I recommend adding playlists of songs you like a lot (either a smart playlist made up of songs with high ratings or just a manual playlist) so when you're on shuffle you don't start thinking to yourself "so that's why I haven't listened to this in a while." :-)

Posted by: BDR | November 16, 2007 4:26 PM | Report abuse

Cool ... now what I'd like is similar.

I have a large ripped CD collection in iTunes.

I'd like to sync libraries like the ones you describe to PocketTunes on my Treo 650.

I believe that this can be done in several steps, which involves using WMP.

Can anyone offer a relatively simple solution?

Posted by: JAE | November 16, 2007 4:40 PM | Report abuse

I keep all my holiday music is one giant playlist, and then choose:

playlist... is not... christmas

So I don't have to use the holiday genre. I can keep my New Wave Christmas tunes filed in the "New Wave" genre.

Posted by: Tony | November 16, 2007 5:25 PM | Report abuse


What would be categorized as "New Wave Christmas"? I think I have to have those tunes!

Posted by: catester | November 16, 2007 7:18 PM | Report abuse

JAE: If you value your metadata, then make sure all your music files are properly backed up AWAY from iTunes and WMP. Apart from the issues they have running on their own, if you have both re-tagging and possibly rearranging your files at the same time, then you have a disaster on your hands.
The two programs don't even delimit field values the same way. Even if you're just using iTunes to convert files to another format, it will touch all your original files.

Tony: WMP allows you to have multiple genres for any track. So they can be both Christmas AND New Wave.

Posted by: Mike | November 16, 2007 7:58 PM | Report abuse

I like this recipe. The only smart playlist that I really would like to have (that i don't have already that is) is one that plays the music that I have been into recently, sort of a "flavor of the month." However, as far as I can tell this is not possible in iTunes because iTunes only tracks the last-played date and not all of the previous dates... or if it remembers the previous play dates and not just the play count, it isn't obvious to me. I wish there was a filter for "times played in the last x days is greater than"

Posted by: Jen | November 16, 2007 11:33 PM | Report abuse

Rob, can you come up with some good playlist ideas for the iPhone? One problem I am encountering is iTunes will list a single selection by an artist under Albums on the iPhone. I will think I have a full album by the artist only to be disappointed when just one song plays. The other most significant problem is trying to have an iPhone selection that is representative of my tastes. Since I have always owned full size iPods until recently, the content on my iPhone feels amputated.

Posted by: Podesta | November 17, 2007 9:21 PM | Report abuse

Nothing Like a Zune in the Morning!
I love the new zunes! Our friends at ZuneScene (yeah baby) are doing a great grassroots job of promoting them too. The iPud has nothing close to ZS, you see, nobody feels passionately about their iPud. The Zoonies have zune body art, Zune haircuts, they name their children Zune, Zunette, Zunisha, Zubert, ... The Zune is a lifestyle, a mindset. They even name their trailers after the Zune. I got my Z-tat last week, I can't post a picture of it because of it's location, but let me just say it's beautiful!
My favorite new Z-colors are the Military Avacodo and the ManPink (pink for real men)! What's yours?

Posted by: Steve ballmer | November 19, 2007 8:17 AM | Report abuse

I use smart playlists in order to vary what is loaded on my 20 G iPod. I have lists for specific artists as well as some for my own compilations (70's rock for instance). When I get tired of listening to the songs in one of these playlists, I empty it and iTunes automatically refills it with new songs.

Posted by: Bruce | November 19, 2007 4:14 PM | Report abuse

I am blind and therefore can't use ITunes. My screenreader can't handle the graphics. Have any of you seen a plug-in for Winamp that can accomplish the same thing? Winamp has full keyboard support, so it's how 99% of blind computer users play music. Thanks for any tips anyone can provide.

Posted by: Monica | November 20, 2007 4:04 PM | Report abuse

Rob (and others), is there a way to make a smart playlist that includes only one song per artist? I have tons of albums by some of my favorite bands (Stereolab, for example) in my iTunes, so every time I make a smart playlist, I end up with tons of songs from each of those - but I don't want to exclude them entirely. Is there a way to automate this? Thanks!

Posted by: Stef | November 25, 2007 3:44 AM | Report abuse

You can't set this up to assess your playing on your ipod, can you?

This only picks up your listening habits while using iTunes?

Posted by: Darrell | December 3, 2007 11:46 PM | Report abuse

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