Of course there's an easy way to setup a playlist to do this already (by creating a sub-list for each pair and then selecting "always randomize" at the parent level), as long as all you want is originals and Weird Al songs bound together. Don’t think I’d want a straight diet of this though . . .
The flaw in this strategy is that it requires that shuffle is turned off. Shuffle modes will also randomize within each sub-playlist, which is not the desired effect.
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- Tony C
my empeg stuff