That’s the struggle I see with a lot of big stars. Even T-Pain, whom isn’t playing as large venues right now, can still pump through a huge medley of songs from hits, to guest verses, to songs he co-wrote. You could see the ‘Arthur fists' when he would only sing 30 seconds of a song.
Side note: You should get on the The List App (http://li.st/) when you write your top 5 biggest artists. I think it would be a good first list. I don’t work them, just a good community, and would like to see your content over there.