This is a variation of Probable Proverbs that involves rephrasing the lyrics to a well known song using as much alliteration with the same letter as possible. Bonus points if the meter works, too, so that one could actually sing the new version, and extra bonus if the rhyme scheme is maintained. Is it possible to get all the way through something like "Stairway to Heaven"? or even "American Pie"? Get out those Thesauri!
I can imagine categories for other types of things besides song lyrics. Nursery rhymes, famous poems, speeches (e.g. Gettysburg address?), Extended lines from books or movies ("This here is a 44 magnum, the largest, etc...you've got to ask yourself one question. Do I feel lucky? Well...Do ya PUNK?" -- how many ways could that be done with alliteration?)