My 3rd grade teacher long long ago used to pronounce it "drawrings". I always thought that was odd, especially coming from a teacher. When I saw the SNL skit I immediately thought of her. I knew a few people who didn't know how to pronounce certain english words, and they weren't foreigners.
Reeboot and re-imagine are just silly euphemistic excuses for the dirty word remake.

They'd frequently show "Simon" vignettes about a little British boy who'd take bubble baths and sing "You know my name is Simonand I like to do dwraw-rings"
I don't know what you're talking about, but there used to be a cartoon or really series of shorts called, "Simon in the Land of Chalk Drawings".
The theme song went, "Well you know my name is Simon, and the things I draw come true. Oh the pictures take me take me over, climb the ladder with you." This is what the sketch was based on.
Each episode was the same. Simon, the titular boy, would draw something on his chalkboard then make his way to a vacant lot, climb the ladder over the wall and there would be a series of chalk fireworks. The land of chalk drawings would appear and whatever it was he drew would appear there. Then he'd go on a little adventure with his chalk drawing friends, things would get wrapped up nicely and it would end with him going home.

Myers is a bit older than I am (I was born in 1977) but like me, he might have also watched "Romper Room" as a kid. They'd frequently show "Simon" vignettes about a little British boy who'd take bubble baths and sing "You know my name is Simonand I like to do dwraw-rings" and "Paddington Bear" cartoon shorts.

Did you just look at my bum?! Bum looker! Cheeky monkey!