Overall, I’ve been quite pleased with my iPod. However, like most tech-heads, I do have my 
power user 
I leave my iPod on shuffle by song all the time; I basically treat it as a personal radio. I like being surprised with what the next song will be - often it is a really bizarre playlist (Lyle Lovett to Eminem to Indigo Girls to Frank Sinatra is a combination you rarely hear on the radio).
Using it in this manner, I wish the iPod had the equivelent of a contextual menu. This menu would help you navigate from the currently playing song to ‘more songs by the artist’ and ‘more songs on this album’ or even ‘more songs with this name’.
In several cases, I have a several artists that have covered the same song and want to hear the other version of it. For example, I was listening to Bob Dylan’s Don’t Think Twice, It’s All Right and wanted to follow it up with the Eric Clapton cover from the Bob Dylan 30th Anniversary Concert.
More frequently, I’ll enjoy the mood from a certain song and want to follow it up with another song by the same artist.
Is something like this in the new iPods?
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alexking.org: Blog adds this Trackback:
iPod Wish List Part III forgot to mention the #1 wish I’ve got for the iPod. I want the shuffle mode options to include a "Random (each song once)" mode.
The iPod seems to fall in love with certain songs/artists from time to time and ignore others. An option …
September 29th, 2003 at 3:55 pm
(a different) Alex adds this Comment:
this is an old post, but if you haven’t figured it out you can get something very close to your #1 wish by creating a Smart Playlist that draws on Last Played information — there are a few different ways to do it, and you’ll have to scale the selection size and time back based on your listening habits and library size, but it should make sense (and you can look at the list in iTunes). This assumes that you use iTunes and synch regularly, though — Smart Playlists are actually loaded into the iPod as static playlists. Skipping to a random point in the list should reshuffle you out of the relisten range, though.
Non-shuffle listens will affect your shuffle playlist, but that’s really what you want, isn’t it?
April 20th, 2004 at 2:50 pm
Alex adds this Comment:
Unfortunately, you need to have a new iPod for the Smart Playlists.
April 20th, 2004 at 3:30 pm