Hi, Every time I boot up my iMac, iTunes starts with it and since I'm lazy I usually just press the play button (F8) on my keyboard so that iTunes plays. However, it always starts with the same song and I'm getting a little tired.

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Is there any way to play a random song when it boots? Or maybe even better select a default artist and play a random song from them? For instance, it could boot with a playlist selected rather than the whole music library I have.

Thanks Edit: Makes me wonder why it does not mimic the iPod application on my iPhone. When I boot up my iPhone it usually plays the last song I was playing, or if it crashed, it plays a random song from the library. Yeah, I just set my iTunes to shuffle mode and when I hit play, as long as I haven't selected a song accidentally before-hand, it plays a random song every time. This is great, but I actually very rarely listen to music in shuffle mode. If only it could remember the last song that was playing when I closed the application and continue from there. This is over my head, I can?t believe this is not how iTunes works right now, at its 10th version. Stupid at its best.

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IPods work that way since they exist. I guess I will just have to file it as a recommendation. Here is a workaround that is quite complicated but has some neat side-effects. It takes some time, though.;) Set up Playlists for every Artist. Or Album or different themes, like 'Spring' or 'Waking up' or 'Party Warm-up' or 'Songs I Love' or something. Put the most important songs in there and essentially stop using that big library. Then, put your library to shuffle.

That way, you can listen to random songs everytime you want to but still have your favourites/the ones you love the most/most important artists/whatever in the regular order. I have a Playlist for every Artist, containing every Album. That way, you can rearrange the songs the way you like. I basically never go into the big library but I do use it for shuffle. I know, it's a lot to ask for but also, once you've done it for the first time, you have a neatly organized playlist-system that you can adjust to your needs like making folders for Artists with playlists for the Albums in there or something.

Whenever you want to listen to some specific music, just head into the playlist. If you just want random songs, head to your big library. Or, alternatively, do one or two clicks more and just play one of the genious mixes iTunes offer.

They usually are pretty great, save for one or two songs.;) But yeah, iTunes acting like the iPod would be way better. Oh and for remembering the last song - get last.fm, scrobble your music and every morning, take a look at your stats - there you have it.

It's complicated, though.:(.