I use iTunes when I listen to songs. My buddy listens using Winamp. We both have Last.fm and PC’s. We have similar music collections, if not same songs here and there.

We like to instant message [IM] each other and listen to songs or entire albums together. He’s in Virginia, I’m in Buffalo.

To do this, we both IM each other and say “ok – hit play – NOW”. We do that, then we IM each other to get each other sync’d up – “10 secs”, “20 secs”, then we are basically in sync.

I WISH IT WAS EASIER. In fact, I wish I could just “tune in” to his music player. It wouldn’t even have to stream the song to me if I already have the same song on my computer, it just needs to start playing the song exactly sync’d with his.

This seems like a plugin that we could both install — like Last.fm, sitting in our system tray. Or maybe it needs to be in iTunes and Winamp.

I’d also love the ability for us to basically create a playlist that plays for both of us — let’s say it’s 10 songs long — he’d get to put 5 songs into the queue, and I’d get to put 5 songs in the queue. This way we could expose each other to new songs that we really love.

It’s basically like a radio station with interactivity and customization to just the people [friends] listening. This could be a few of my friends and I doing this together — exposing each other to the same songs.

I don’t know what the revenue model is — but maybe it’s “buy this track”, and if the thing really takes off you’ll probably have influencers and have data on what tracks are getting the most exposure between friends. But hell, I’d personally pay money for this software — but you’d likely need to make it free to gain traction.

Here’s an example IM session between us regarding a new track by Wolf Parade: [pardon the vulgarities]

Steve: 10 secs

i wish we could easily collaboratively listen

Steve: i do.