I had to vote Uncool...
BUT, I did love every bike I had from Raleigh, which I think numbers as 6. I still have a Road Ace (Shimano 600 index model), which got a little small for me after a few years and so it was refurbed and gifted to my Sister who still uses it, its 20 years old now.
Raleigh did make some very cool bikes, but they also made plenty that were not, the balance therefore falls on the uncool side for me. I never had a problem with the quality of a Raleigh bike, and had many happy years riding them - as a kid you could get an Iron Horse BMX for about £30.00 when a Burner was over £100, no one was going to be persuaded on the price - the Burners were cool then.
The BMX probably stopped Raleigh going under quite a few years ago, but some of the thing they have produced since have not been inspiring and I suspect that its only places like this website that you can truly appreciate some of the great (and cool) things they have done in the past.