The cool factor- who has it?

@foggyus91 yeah, not really a debate on vocal chops... if that were the case Joe Strummer & Mick Jones would be in right the mix of your "Tiny Tim" analogy lol. Point is, I think we both find Chet Baker super cool, in spite of his limited vocal abilities, as was asked by the OP 

Mark Knoffler

@bgross Yes indeed, I agree.

if that were the case Joe Strummer & Mick Jones would be in right the mix of your "Tiny Tim" analogy lol

Miles Davis and whoever is #2 is not even close. Miles was cool before being cool was cool. One might assume that anyone who can play a horn should be able to sing as well. Chet Baker disproves that assumption.

We can say anything. We can propose our "taste" as truth...

But facts spoke themselves sometimes : 

I pick and past it from google :

 «Chet Baker’s first vocal album, Chet Baker Sings, released in 1954, was a significant success that propelled him to stardom as both a trumpeter and vocalist. The album, featuring his interpretations of popular standards, was a hit with audiences and critics, and helped establish him as a prominent figure in the West Coast cool jazz scene »

Then Say it in this way : Chet Baker sings crappy  and it is my opinion...

 And i will say it  my way and i am not alone saying it : "the Prince of cool" was Baker because he sing as he play : cool with no bravado...

Not sure who you're directing that to... my opinion, CB has legendary swag and I love CB Sings because of exactly what it is; a bold attempt to let his voice be heard. It's a great LP for so many reasons. I'm on board, Chet Baker = cool!