I don't think an artist can make 10-20 classics but I agree some artist are able to stay relevant. It's about experimenting as you said, try to mix their style with the new sound without it becomes to corny and when you take chances as an artist like that it's usually a hit or miss, therefore I don't think an artist can have that many "classics".
I would like to add Ghostface and Scarface to your list.
I would like to add Ghostface and Scarface to your list.
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