I don't think the stocks with big drops were ever meant to be cheeked. The thread here talks about 3" drops, but there are a lot of guns with even more than that - some guns just can't be crawled. Pictures of turn-of-century shooters show them pointing the guns, heads held high.

It can be done competently. I used to shoot skeet with an old guy who shot that way, head high. Clean air between his cheek and the wood. He just pointed the gun, a fine demonstration of eye-hand co-ordination. It was kind of disturbing to watch, but he was an outstanding shooter. He was v knowledgeable, modest, and had a good sense of humor. Some of the things he said hinted that he might have been ex-AMU from back in the sixties.