That dialog happens when you've added some songs to Up Next, then double-click on a new playlist/album. Double clicking on a playlist/album means play this song and all the ones that come after it in the album. So you've given itunes conflicting instructions. Without that dialog, there's no way of resolving the conflict without pissing someone off.

> But they should just have moved the song you selected to the top of the Up Next queue.

You can do this by right clicking a song, and clicking Play Next. There is no dialog for that. But imagine how frustrating it would be if they adopt your proposed behavior for someone double clicking on an album. What if I just want to clear everything and just play this album? I want to hear it now, not wait until this song ends.

Honestly, I don't know, about that particular detail. I haven't seen that, though. Which version of iTunes was this?

Anyway, the question itself isn't that offensive, right? They want to know whether you intend to play your selected song and THEN the things in queue, or clear out the queue instead. I admit that a modal dialog is...sub-optimal here, but I'm not sure how else to do this.