I have a nice program called
Instant Elevator Music, which, quite appropriately, plays elevator music (or rather, music of the user's choice) when it detects a loading bar. I have exactly one song in that program's playlist. Quite appropriately, that song is a percussion cover of
Sburban Jungle (the theme song for Sburb from Homestuck, hence the choice).
...Assuming a sufficiently long loading time, I may have listened to that song as many as 30 times or more in a row at some point.
I don't think the program keeps track (I'm on a different computer right now, so I can't check). I never tire of the song, though, so everything works out.
(*edit: It doesn't keep track of play count, but it *does* keep track of total play time (or, as it calls it, how long I've been "stuck in an elevator"). My laptop's previous hard drive bit the dust recently, so this count only totals the past month or so, but that song's played for 48 minutes and 3 seconds since then.*)