I downloaded the new Magnolia Electric Co. album on Sunday (don't worry, Jason Molina, I promise to buy it when it comes out next week), and I was going to listen to it while I was trying to sleep. I loaded it into iTunes. I clicked the shuffle icon and the repeat icon so that if I fell asleep before the album finished it wouldn't play all night.
On Monday morning (well, afternoon; it was Labor Day, after all) I woke up and it was still playing. Turns out that I only hit the repeat icon once that it repeated the song that was playing when I got in bed. I guess I fell asleep before I realized what happened.
It played 164 times.
And of course the first thing I thought was, "Shit! That's totally going to fuck-up my Last.fm statistics!"