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Shows like John Oliver could go 20+ years easily. If he’s happy and making the exact show he wants to make, I don’t see why he wouldn’t keep going. Bill Maher is on season/year 21. And it really can’t be that expensive compared to their other tent poles.
I’ve got two of Ryan North’s books, “Romeo and/or Juliet” and “To Be or Not to Be” on my bookshelf, but until seeing a Dinosaur Comic again just now, I entirely forgot the connection.