Oooh! I love this game! A group of friends of mine would play a variant of this where:
Biz Markie (“Oh baby you, you got what I need…”) sings any song at any location/event in history
You can come up with some doozies. So, to conform with the OP, my songs will all be sung by Biz Markie, with the bonus of giving a location:
Biz Markie, “We All Live in a Yellow Submarine”, Battle of Waterloo
Biz Markie, “I’m a Little Teapot”, Impeachment Trial of Andrew Jackson
Biz Markie, “The Good Ship Lollipop”, The Conception of LeAnne Rhymes
Faith No More worked it into their song “We Care A Lot” in concert. Mike Patton would start singing “oh-oh oh-oh-oh oh-oh-oh-oh oh-oh oh-oh-oh the right stuff…we care a lot!” And seque back into the original song. If you want to see it, it’s on the “You Fat Bastards” home video.
I once had a long, rambling nightmare which included a duet. Ethel Mermen and Louis Armstrong. Singing “River Deep, Mountain High”. It isn’t funny in the sense that some of the other pairings here are funny, but it was bizarre enough that I had to get it off my chest. Thank you.