I think Cannondales are very good bikes, would love a BOTE. Made very well, good graphics and can look really good.
BUT that doesn't make them cool. Cool is something that you can't quite put your finger on or describe properly.
Cool isn't being technically advanced, having great paint jobs or breaking any moulds.
It's something much more.
And Cannondales just aren't there. Maybe it's some of the wacky designs. Maybe it's their (maybe poorly deserved) reputation for cracking. Maybe it's because they eventually sold out. I don't know.
I don't think they are UNCOOL but they certainly are NOT COOL. As there is no middle option I have to vote in the negative.