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I can only think of 2 that would count that I wouldn't be cheating: They Might Be Giants and Weird Al. If it's their full discography and any other releases they've done, that's already way too much music for me to ever listen to in my lifetime with my listening habits.
I would love to cheat with something like Hatsune Miku, but that wouldn't be fair considering it's tons of people using software to create songs with that specific voice rather than a single singer/band performing.
I cannot think of anyone else I listen to with nearly as expensive of a list of music as TMBG or Weird Al, so I'd probably end up going to the next best thing: Jam Hsiao. He's got a lot of music, so I'd have a lot to choose from. Choice would be the spice of life for me.
Absolutely no clue for the 4th, so I'd probably pick a group that I like at least a couple of their songs and think they have a large amount of music: Meat Puppets.
In the end, due to their probably high song count, these would probably be my top picks right now.