How many pieces of music do you have multiple recordings of?
In pop/rock, it's mostly limited for me to They Might Be Giants. With 475 TMBG tracks in my library including multiple compilation albums (which probably shouldn't count) that's no surprise. Some of the double-ups are studio versus live versions.
There's a lot of doubling-up on Jazz standards, Mozart and Bach (helped by the fact I have both the complete works of Mozart and Bach as well as many individual recordings).
But what about more than 5 recordings? I can think of only three off the top of my head: two of them are Charlie Parker's Yardbird Suite (my favourite Jazz piece) and Bach's Goldberg Variations (including 3 recordings just of Glenn Gould if you count the Zenph reconstructions).
The third is in a totally different category as I actually have over 10 recordings of it.