Originally Posted by Kajmere
You answered your own question with a quote.
By saying 'I could care less' means you care so much, you could actually care less about something. The actual term is 'I couldn't care less'. This simply implies that you don't care at all, therefore you cannot possible have any more 'care' left to actually care more. It's a significant difference.
Edit: I see macho man fan beat me to the punch
On topic; as boring as the streak is, it's still probably one of the best matches on the 'mania card. I actually didn't really think anything of the streak until the Shawn Michaels match. I'm sure this was when the streak became this huge thing?